Alkite Synthesis

Alkite Synthesis
On 1/7, the Alky started to only process FCCU BB and no longer process Coker BB. Alkylation
chemistry neither likes contaminants nor diluents. Contaminants are direct acid consumers. The
more contaminants in the feed, the more often the unit will be at an acid constraint. Diluents do not
reaction in alkylation chemistry but they take up space and decrease the effective area for isobutane
and olefin to contact. With less contact, side reactions like polymerization are more likely to occur;
polymerization reactions are a direct acid consumer.
Comparing the FCCU and Coker BB, Coker BB contains far more contaminants and diluents than
FCCU BB (see Table 2, pg.4).
By lowering the amount of contaminants and diluents, acid consumption was reduced ... Show more
content on Helpwriting.net ...
The best way to decrease acid residence time is by lowering the level in the settlers. PAR has
abnormally high settler levels (45–60% vs. typical 15–20%). The acid consumption impact of
running at the appropriate levels in the settler is –0.15 lb/gal or 1.3 MM$/yr in savings (1.1 MM$/yr
at cooling constraint and 1.3 MM$/yr at acid constraint). Process Support recommends maintaining
a level of 15–20% in C and A settler and a level of 40% in B settler. B settler should be run higher
than C or A because of risk of sending lighter hydrocarbons to the spent acid tank.
3. Emulsion recycle
Emulsion recycle minimizes undesirable side reactions, such as polymerization, in the acid settler by
keeping the olefins and alkyl sulfates (esters) in contact with isobutane. This results in improved
Alkylate quality with reduced acid consumption. Process Support recommends opening all emulsion
recycle valves 100%.
In general, maximum acid recycle rates and minimum acid residence time promote better Alkylate
product quality, and decrease the potential for polymerization. Net effect of implementing these
steps is $5.3 MM$/yr due to reduced acid consumption and lower endpoint.
Operations began lowering settler levels and opening acid recycle valves in February. Progress on
this effort will be reported in the next bi–monthly
... Get more on HelpWriting.net ...

Hydration Of Alkenes Lab Report
Introduction Hydration of alkenes is the acid–catalyzed addition of water to a carbon–carbon double
bond, which will form an alcohol. The alkene in this experiment is norbornene. An equilibrium can
be established between hydration and the opposite reaction, dehydration. These are two competing
processes. The position of the equilibrium is dependent upon the reaction conditions, which are:
hydration of a double bond requires excess water to drive the reaction to completion, whereas,
dehydration of an alcohol required the removal of water in order to complete the reaction. The
product produced is exo–norborneol.
The percent yield of the reaction can be calculated by using this equation:
% yield=(mass product obtained (experimental))/(mass product (theoretical))×100.
Procedure
Results
Table 1: Data collected in grams for the experiment Weight (in grams)
Norbornene 0.519
Pre–weighed vial 7.693 ... Show more content on Helpwriting.net ...
The crude weight of the product formed was 0.067 grams. The theoretical mass that was used to
calculate percent yield was calculated using the weight of norbornene, 0.519g and converting it to a
product weight of exo–norborneol, which was calculated to be 0.620g. The percent yield was then
calculated to be 10.81%, which can be found in table 3. A melting point was determined from the
crystals formed in the vial by using a DigiMelt melting point apparatus. The melting point for the
crystals was 90.0–106.8°C with a range of 16.8°C, which can be found in table 2. The literature
melting point value for exo–norborneol was found to be 124–126°C with a range of 2.0°C, which is
larger than the melting point obtained in the experiment. Because of steric hindrance from other
groups on the carbocation, the nucleophilic attack of water occurs solely in the exo position, located
farthest from the longest bridge, as opposed to the endo position located closest to the longest

Essay about Wittig Reaction: Synthesis of Trans-Stilbene
The purpose of this experiment was to perform a wittig reaction, the horner–emmons wittig
specifically, reacting an aldehyde with an ylide to make an alkene. This particular variation of the
wittig reaction has several advantages: It gives only the trans product; it uses a much milder base
that is easier to handle; and it gives a water soluble byproduct which is easy to separate from the
product. The reason that these advantages occur is a change in the structure of the ylide. Instead of a
tripheylphosphine ylide, we use a diethylphosphonate ylide. The protons are much more acidic and
its byproduct is negatively charged.
The reason why we chose to create trans–stilbene is become of its many practical applications.
Stilbene exists as ... Show more content on Helpwriting.net ...
This modification is similar to a standard Wittig reaction in that the first step, which has already
been done for you, is the reaction of a trialkyl phosphite with a suitable alkyl halide as shown below
in two steps:
In the first step the trialkyl phosphate acts as a nucleophile and, in a typical Sn2 reaction, forms a
phosphonium salt. The salt is unstable and a halide ion X displaces R in the Sn2 manner to form a
dialkylphosphonate. It is the phosphonate that, in the presence of base, is converted to a Wittig–like
reagent. Normally the Wittig reagent is an ylid and neutral, but the modified Wittig is analogous to
the carbanion of an aldol intermediate. Due to its resonance forms, the phosphonate anion is able to
attack the carbonyl much like acarbanion in an aldol reaction to give an oxyanion species. This is
where the analogy with the aldol reaction fails. The oxyanion undergoes a reaction analogous to
nucleophilic substitution at an unsaturated center to form the olefin, normally as the E isomer, and a
water soluble phosphonate anion. In this particular experiment, diethyl benzylphosphonate is used
with benzaldehyde as the carbonyl component. Since phase transfer conditions are used, we can use
a weaker base, the hydroxide ion. The reactivity o the anion formed is very high, resulting in
excellent yields of trans–stilbene. The trans form of Stilbene is more favored than the sterically
hindered cis form. Although

To Convert A Ceclohexanol To Cyclohyde
Aim The purpose of this experiment was to convert a cyclohexanol to a cyclohexene through E2
reaction by dehydration.
Introduction
An elimination reaction is a reaction where a molecule is lost in the reaction which leads to a
formation of a double bond. An elimination reaction is very useful in producing a double or a triple
bond. An E2 reaction is one of the elimination reactions where a base deprotonates from the
adjacent carbon which leads to the formation of a pi bond and kicks out the leaving group. E2
reactions happen in a one concerted step without any carbocation formation. Unlike a substitution
reaction, an elimination reaction needs a strong base and a weak nucleophile, so the base is able to
deprotonate without competing with substitution. Strong bases such as ... Show more content on
Helpwriting.net ...
The distillate was swirled and mixed and was transferred to an Erlenmeyer flask. CaCl2 was added
to the flask so it can absorb any water which formed as the by product. Next, the product was
transferred into a vial without the CaCl2 The mass of the product was recorded. To test for the
alcohol, 3 test tubes were labeled for cyclohexanol, cyclohexene and the product. 5 drops of
Ammonium cerium (IV) was added into all the three test tubes. In the first test tube, 2 cyclohexanol
was added. In the second test tube cyclohexene was added and for the third test tube 2 drops of
product was added. The observations were recorded. Similarly, for the alkene test, 3 test tubes were
labeled, and 20 drops of dichloromethane was added to each. Next, cyclohexanol was added to the
first tube, cyclohexene in the second test tube and the product in the third test tube. Then, 5 drops of
PBP which is the source for Br– was added to each test tube and the observations were recorded.
Table of Chemicals
Compound Structure Physical Appearance Boiling point Safety Hazards

Synthesis Of Stilbene Dibromide
Synthesis of an Alkyne: Bromination of Stilbene and Dehydrohalogenation of Dibromide Maya
Yagan Fall 2015 Lab Section 355–01 Lab Partner: Kristine Thao Abstract Trans–stilbene (1,2–
diphenylethene) was synthesized in a two–step reaction. Trans–stilbene was brominated to give
meso–stilbene dibromide in the first reaction. The stilbene dibromide was heated with base in order
to induce dehydrobromination. One of the methods used throughout this experiment was vacuum
filtration. An 81% yield was obtained due to a few minor errors. The compound seemed to be pure
due to the relatively close melting point ranges. Introduction The experiment that was conducted in
lab was synthesis of an alkyne. Now, what exactly is an alkyne? An ... Show more content on
Helpwriting.net ...
The mixture was warmed in a hot water bath until the solid dissolved and then 1.0 g of pyridinium
hydrobromide perbromide was added. With a little acetic acid, the crystals of reagent from the sides
of the flask were rinsed and then heated for an additional 1–2 minutes. Immediately, stilbene
dibromide precipitated as small plates. Once the mixture has been cooled under tap water, the
product was collected by vacuum filtration. Ice cold methanol was used to wash and the isolated
solid continued to dry for a few minutes. To achieve maximum drying, the crystals were pressed
with a spatula. The yield, percent yield, and melting point of the product was recorded. About 0.8 g
of stilbene bromide should've been obtained with an expected melting point range of 236℃–237℃.
The IR spectrum was obtained and compared to that reported for the pure

Dehydrobromination Lab
For this experiment, a dehydrobromination was performed on a meso–stilbene dibromide to form an
alkyne. The meso–dibromostilbene was converted into diphenylacetylene, an alkyne, through two
E2 elimination reactions. The dibromostilbene reacted with a strong base, potassium hydroxide, at a
very high temperature. The hydroxide, from KOH, deprotonated one of the aliphatic hydrogen
atoms or protons which formed an alkene and broke one of the C–Br bonds releasing the bromine.
This process does not take much energy to remove one of the H–Br. This process was completed
twice, and the second C–Br bond was broken, and an alkyne formed. This process was more
difficult due to the rotation needed to perform the initial elimination. The elevated temperature ...
Show more content on Helpwriting.net ...
Very high activation energy is required for this reaction to occur. Therefore, heat is applied at around
190 degrees Celsius. This breaks the second C–Br and C–H bond which forms an alkyne to produce
diphenylacetylene. The E2 elimination occurs on hydrogen atoms that are anti–periplanar to the
leaving group which means that the hydrogen and bromine are on opposing sides. The ideal
orientation of the bromine and hydrogen is anti–coplanar but this not achievable. This is caused by
the orbital overlap of the sigma (σ) orbital that makes up the C–H bond and the antibonding sigma,
(σ*), orbital of the C–Br bond. Therefore, bond rotation is needed to make the dibromostilbene into
the anti–periplanar orientation. The first elimination reaction can occur once it is in this orientation.
When these two groups are right next to one another there is very little orbital overlap that occurs
and requires much more energy to perform the second elimination

Dehydration Of 2-Methylcyclohexanol And
Introduction
An elimination reaction is when an atom or group of atoms, the leaving group, leaves the molecule
along with the loss of a hydrogen atom that is part of an adjacent carbon that results in an alkene
(Ketcha, 98). Dehydration is an example of an elimination reaction. Just likes its opposite
(hydration, the addition reaction), it could also result in multiple products: one product would be
"major" where it is one that was mostly form as it is mostly stable, and one is the "minor" which is
less stable then the major and least likely to form (Ketcha, 98).
The mechanism of dehydration is a three step process. First the protonation of the –OH, then the
loss of the H–O–H + Leaving group, resulting in a carbocation intermediate, and finally the removal
of H+ ... Show more content on Helpwriting.net ...
Procedure
(Ketcha, Daniel; Turnbull, Kenneth; Grieb, Jonathan. Organic Chemistry Laboratory Experiment,
"Dehydration of 2–Methylcyclohexanol and Gas Chromatography." Cincinnati, OH: Van Grinner
Publishing, 2016.)
2–Methycyclohexanol (15mL) were added to H3PO4 (1mL) and H2SO4 (3 drops) in a 100mL
round bottom flask. The distillation apparatus was assembled and the mixture was moderately
heated to avoid bubbling during the distillation process. During this time, some of the equipment
was not 100% secured, and some product was lost. Distillation was stopped when a black, oily
substance started to form at the bottom of the flask. The distillate was collected in the Erlenmeyer
flask, at the temperature of 109 degrees C. The organic layer was dried using the anhydrous MgSO4.
The MgSO4 was filter off and the alkene mixture was collected. The liquid alkene was weigh.
The final product was analyzed using the gas chromatography, where the retention time of each
product was determine and compared to the standard

Alkene Addition Bromination Essay
Old Dominion University
ORGANIC 214
Alkene Addition
Submitted by:
Alkene addition: Bromination of (E) Stilbene
Introduction:
In this lab we used the greener approach, which involves the addition of bromine across a double
bond. When bromine reacts with E–stilbene (trans–1,2–diphenylethene), two new chiral carbons are
created from the sp2 carbons, therefore 3 different dibrominated stereoisomers are possible: meso–
(1R,2S), or the raceminc mixture–(1R,2R) or (1S,2S)–dibromo–1,2–diphenylethane (Gilbert, 2010).
When the bromination ion intermediate proceeds through a stereospecific mechanism, then the meso
dibromide is formed exclusively. The racemic dibromides are formed from the concerted syn
addition if the mechanism proceeds ... Show more content on Helpwriting.net ...
When the product was completely dry two different melting points were recorded, averaged and
then compared to the standards in order to identify the product. The theoretical yield and percent
yield were also calculated.
Results:
Reagent | Amount | (E)Stilbene | 0.200g | Cold Acetic Acid | 4mL | Pyridinuim Tribromide | 0.394g |
DI water | 4mL | Methanol | 3mL |
Table 1: Amount of Reagents Used
Reagent and Products | Standard MP | Product MP1 | Product MP2 | Avg. MP | (E) Stilbene | 122°C
–125°C | n/a | n/a | n/a | Dibromostilbene Meso Favored | 241°C – 243°C | 242.2°C –246.4°C |
243.0°C–247.1°C | 242.6°C –246.7°C | Dibromostilbene Racemic Favored | 113°C –114°C | n/a | n/a
| n/a |
Table 2: Melting Point
Percent Yield Calculation | 0.200 g (E)–stilbene / 180.25 g/mol (E)–stilbene = | 0.00111 mol (E)–
stilbene | 0.00111 mol (E)–stilbene X 1 mol dibromostilbene / 1 mole (E)–stilbene = | 0.00111 mol
dibromostilbene | 0.00111 mol dibromostilbene X 340.058 g/mol dibromostilbene = | 0.377 g
dibromostilbene | (Actual yield 0.275 grams / Theoretical yield 0.377 grams)x100 = | 72.9% percent

yeild |
Table 3: Calculations
Discussion and

Lab Report On The Dehydration Reaction Of 2...
DEHYDRATION OF METHYLCYCLOHEXANOLS
Nicholas Van Horssen
CHMY 321
TA: Michael Giroux
10/31/17
Introduction: The purpose of this lab was to carry out a dehydration reaction of 2–
methylcyclohexanol by heating it in the presence of phosphoric acid and determining which alkene
product would be the major product. Methylcyclohexanols were dehydrated in an 85% phosphoric
acid mixture to yield the minor and major alkene product by elimination reaction, specifically E1.
The alkenes were distilled to separate the major and minor products and gas chromatography was
used to analyze the results and accuracy of the experiment. The hypothesis was the major product of
the reaction would be the most substituted product. This conclusion was made because of ... Show
more content on Helpwriting.net ...
Distillation of the first product began at 83 °C. A Pasteur pipette was used to remove 1–ml of the
distillate into a vial. A second vial was filled with distillate until it reached 1–ml. As the second vial
is being filled, observe the temperature and remove the apparatus from the heat source if there is an
observed drop in temperature. Once the distillate had been collected into two separate vials, both
distillates were washed with aqueous sodium bicarbonate (1.5–ml, 5%). The aqueous layer (lower)
was extracted from both vials using a pipette and put into a chemical waste bin. The organic
(alkene) layer was then dried with anhydrous calcium chloride pellets (3 pellets per vial). Both
distillates were analyzed using gas chromatography, and each peak shown was identified to be one
of the alkenes. Analysis of the graph was used to determine the major and minor products of the
reaction.
Results: M.W. (g/mol) Boiling point (°C) Density (g/mL)
2–methylcyclohexanol 114.2 166 0.930
Phosphoric Acid (85%) 98.0 – 1.70
1–methylcyclohexene 96.2 110 0.813
3–methylcyclohexene 96.2 104 0.801
Table 1: Properties of the reagents and possible products for the reaction. The boiling point of
Phosphoric acid is not important because it is a reagent.
Figure 2: Gas Chromatography analysis from the first sample. From top to bottom the peaks are
ordered as followed: 3–methylcyclohexanol (A), 1–methylcyclohexanol (B), and 2–
methylcyclohexanol

The Synthesis Of An Alkene 4-Methylcyclohexanol
The goal of this experiment was to synthesize an alkene (4–methylcyclohexene) from an alcohol (4–
methylcyclohexanol) by dehydration. The reaction, consist of 4–methylcyclohexanol, phosphoric
acid, and sulfuric acid, was refluxed at a given time frame. The product was isolated by distillation
and purified by adding sodium chloride to help the extraction. The final product had a 125% yield
and was characterized by the IR spectroscopy and chemical reaction. The alkene resulted in a
colorless liquid after adding molecular bromine dissolved in dichloromethane.
Introduction One of the most important things organic chemists do is synthesize new and complex
structures from simpler structures by chemical reactions. The techniques done in ... Show more
By heating to refluxing, the temperature and thermal energy were controlled during the experiment.
Heating the reaction is important because it is required in order for the bonds to break to cause a
chemical reaction. Breaking bonds also means requiring energy and that is where activation energy
comes into play. All chemical reactions has to overcome an energy barrier to generate the product
from the reactant. The chemical yield is a measurement of how efficient the organic reactant was
synthesized into the desired product. The chemical yield will be lower if there are unreacted
reactants or too many side products in the reaction. Unless the product was isolated properly during
the distillation, it will negatively affect the chemical yield too. The chemical yield is measured by
dividing the number of moles of product to the number of moles of reactant then multiplying it by
100 to get the percentage. The final product formed was characterized by using an infrared
spectroscopy and chemical reaction. The IR spectrum was expected to show a carbon double bond
(alkene) and many C–H sp³ hybridization bonds (alkyl) from the final product. This was compared
to the authentic sample with its vibrational bonds. Once done identifying how close the sample is
with the authentic sample, that would be the evidence to support the product's

Anti Addition To Stilbene: Preparation Of E-Bromine
LAB 4: ADDITION REACTIONS OF ALKENES: BROMINATION OF (E)–STILBENE
(Preparative) Introduction
The first purpose of this lab was to predict the stereoisomeric composition of alkenes brominated
through electrophilic addition by creating a reaction mechanism for (E)–Stilbene. The second
purpose of this lab was to brominate (E)–Stilbene to Stilbene Dibromide through the
aforementioned method. The third purpose of this lab was to ascertain a rough estimate of the ratio
... Show more content on Helpwriting.net ...
This low yield could also be the result of the experiment not being performed optimally resulting in
the reaction not completing fully which was is not supported by the observation of the
decolorization of solution. The melting point of the Stilbene dibromide product was 211 – 220 °C.
Because of the broad melting point range (larger than 5 °C) the product is impure. These impurities
are likely a result of the improperly collecting the product during vacuum filtration. Either the
compound was not filtered correctly or the filter paper flaked off during collection. Another possible
sources for the impurities the glassware used during the experiment not being cleaned properly
resulting in unwanted compounds in solution. Although vacuum filtration can somewhat get rid of
this product the vacuum filtration apparatus could itself be improperly washed. Another source of
error could be a result of incorrect observations of the melting point. The melting point proves the
predicted composition of mostly meso and slightly D/L as the experimental melting point is close to
the actual melting point of meso but depressed. The large depression of over 20°C from the meso
melting point may be a result of the extreme melting point variation of meso and D/L that occurs
naturally or (more likely)

Alkenes Have A Carbon-Carbon Double Bond Of Norbornenes
Introduction
Alkenes are molecules that contain a carbon–carbon double bond and they are hydrated by acid–
catalyzed addition of water to that carbon–carbon double bond. This leads to the formation of an
alcohol. Two competing processes, hydration and dehydration, establish an equilibrium. The
position of the equilibrium is dependent on the condition of the reaction. While hydration of a
double bond requires excess water to drive the reaction, dehydration of an alcohol requires the
removal of water to complete the reaction. A carbocation is then formed by the addition of a proton
to the double bond of norbornene. Steric hindrance determines how the reaction takes place. During
such a reaction, the side of the carbocation, formed by the addition

Friedel-Crafts Acylation Lab Report
The Friedel–Crafts acylation reaction is an important and valuable electrophilic aromatic
substitution reaction. First introduced in 1912 by Charles Friedel and James M. Crafts, this reaction
allows large multi–step reactions to take place, and creates numerous types of products.1 Today,
Friedel–Crafts reactions are among the most used electrophilic aromatic substitution reactions. In
the electrophilic aromatic substitution class of reactions, functional groups are substituted onto an
aromatic ring.2 Products such as ketones, hydrocarbons and phenols, phenol ethers, and keto acids
can be produced by electrophilic aromatic substitution.1 These products can then undergo other
reactions, allowing for the creation of many types of products. The products acquired can be used
for a range of purposes, such as pharmaceuticals, pesticides, dyes, etcetera.3 In particular, Friedel–
Crafts acylation reactions result in a product containing a ketone. ... Show more content on
Helpwriting.net ...
The functional group added during a Friedel–Crafts acylation reaction, deactivates the ring, resulting
in a mono–substituted ring rather that a poly–substituted ring, which is produced from a Friedel–
Crafts alkylation reaction.4 The mono–substituted product is then further reduced to get an alkyl
substituted ring instead of yielding a product containing a ketone. To obtain the ketone product, an
acyl group is added to an aromatic ring. However, for this reaction to take place, no electron
withdrawing groups can be present on the aromatic ring, and an acyl halide must be used to obtain
the acyl cation.5 These limitations are met, in the Friedel–Crafts acylation reaction of anisole with
acetyl

Part a: Dehydration of 1-Butanol & 2-Butanol/Part B:...
Ashley Droddy
CHM 235LL–Monday, 3/19/2012 & 3/26/2012
Part A: Dehydration of 1–butanol & 2–Butanol/Part B: Dehydrobromination of 1–Bromobutane
& 2–Bromobutane
Abstract
The objective of this experiment is to successfully perform a dehydration of 1–butanol and 2–
butanol, also dehydrobromination of 1–bromobutane and 2–bromobutane to form the alkene
products 1–butene, trans–2–butene, and cis–2–butene. The dehydration reactions react under and
acid–catalysis which follows an E1 mechanism. It was found that dehydration of 1–butanol yielded
3.84% cis–2–butene, 81.83% trans–2–butene, and 14.33% 1–butene, while 2–butanol is unknown
due to mechanical issues with the GC machine. For the dehydrobromination, with the addition of a
... Show more content on Helpwriting.net ...
That the more stable alkene trans–2–butene, is the major product at approximately 82%. While, the
two minor products would be 1–butene at 14%, and cis–2–butene at only approximately 4%.
Although, dehydration was not performed on 2–butanol, it would also produce the 3 isomeric
alkenes like 1–butanol via an E2 mechanism. The percentages would probably be very similar as
well. With trans–2–butene, being the major product, and cis–2–butene and 1–butene being minor
products as well. The GC results would appear again very similar to 1–butanol with 3 peaks
representing the 3 alkenes produced, however, 2–butanol has a lower BP, so it takes longer to react
and produce gaseous mixture because it is a secondary alcohol.
Part B: Dehydrobromination of 1–bromobutane & 2–bromobutane Compound | Temperature
(⁰C) | Products | Peak Area(mm2) | % Composition | 1–bromobutane | 90 | Trans–2–butene | ––––– |
–––– | | | Cis–2–butene | ––––– | –––– | | | 1–butene | 17500 | 100 | 2–bromobutane | 80 | Trans–2–
butene | 2469 | 49.95 | | | Cis–2–butene | 3336 | 13.09 | | | 1–butene | 8741 | 36.97 |
–(GC) Calculations for relative amount of products:
1–bromobutane:
Total peak area=17500 mm2
17500 mm2/17500 mm2x100%=100%, 1–butene
2–Bromobutane:
Total peak area=6679mm2
2469 mm2/6679 mm2x100%=36.97%, 1–butene
3336 mm2/6679 mm2x100%–=49.95% trans–2–butene

8741 mm2/6679 mm2x100%=13.09% cis–2–butene
1–bromobutane with a strong base reacts

E1 And E2 Synthesis Lab Report
In this experiment, the objective is to use an acidic catalyst to make 2–methyl–2–butanol undergo an
E1 reaction and to use gas chromatography to analyze the remaining mixture of alkenes. Elimination
reactions are ones that focus on the removal of a molecule, without replacement. There are two
different elimination reaction mechanisms, E1 and E2. Both reaction mechanisms involve the
removal of a molecule, leaving group, and a double bond (pi bond) being formed. In this
experiment, an E1 reaction is performed by using sulfuric acid as a catalyst which dehydrates the 2–
methy–2–butanol. This results in a mixture of alkenes (Weldegirma 2016). E1 reactions are both
unimolecular and reversible at every step. An E1 reaction involves 2 vital steps.

Solid Phase Of Polymer Bound 2
A 1,3,4–thiadiazole library was constructed by solid–phase organic synthesis. The key step of this
solid–phase synthesis involves the preparation of polymer–bound 2–amido–5–amino–1,3,4–
thiadiazole resin by the cyclization of thiosemicarbazide resin using p–TsCl as the desulfurative
agent, followed by the functionalization of resin by alkylation, acylation, alkylation/acylation, and
Suzuki coupling reaction. Both the alkylation and acylation reactions chemoselectively occurred at
the 2–amide position of 2–amido–5–amino–1,3,4–thiadiazole resin and the 5–amine position of 2–
amido–5–amino–1,3,4–thiadiazole resin, respectively. Finally, these functionalized 1,3,4–thiadiazole
resins were treated with trifluoroacetic acid in dichloromethane, ... Show more content on
Helpwriting.net ...
Lee et al. compared the binding affinity of compounds containing 1,3,4–oxadiazole or 1,3,4–
thaidiazole in the same chemical structure toward CB1 receptor in the process of development of
obesity drug.9 Both 1,3,4–oxadiazoles and 1,3,4–thiadiazoles were also used for the development
potent antibacterial agent by Kumar et al.10 Asai et al. reported dramatic difference in the binding
affinity between 1,3,4–oxadiazole and 1,3,4–thiadiazole toward signal transducers and activators of
transcription.11 Because of these biologically interesting properties of 1,3,4–thiadiazole and 1,3,4–
oxadiazole, these core skeletons have been targeted for synthesis by organic and medicinal chemists,
and as a result, many synthetic methodologies have been developed in the literature.12 Among these
synthetic methodologies, solid–phase synthesis effectively facilitates the generation of various
1,3,4–thiadiazoles and 1,3,4–oxadiazoles in a short time.13 In our own research area, we have
developed solid–phase synthetic methodology to produce 1,3,4–oxadiazoles and 1,3,4–
thiadiazoles.14 However, unfortunately our methodology was limited to synthesize diverse 1,3,4–
thiadiazole derivatives. It was only suitable to generate p–nitro substituted 1,3,4–thiadiazoles
(Scheme 1a). To improve over

Diels Alder Reaction Lab Report
Organic Chemistry–Diels Alders Reactions Introduction Diels–Alder reactions are organic chemical
reactions which involve [2 + 4] cycloaddition. The cycloaddition takes place between the conjugated
dienes and the substituted alkenes (dienophiles). This interaction between the dienophiles and
conjugated dienes result in the formation of substituted cyclohexene system. In 1928, two scientists
(Kurt Alder and Otto Diels) jointly invented Diels–Alder reaction. This invention enabled them to
receive the award (Nobel Prize in Chemistry) in 1950. Diels–Alder reactions are used in organic
chemistry to prepare compounds with 6–membered systems. Diels–Alder reactions are also
fundamental in the synthesis of compounds with TT systems like imines and carbonyls. The
application of Diels–Alder reactions in TT systems leads to the formation of heterocycles in a
reaction referred to as the hetero–Diels–Alder reactions. In some specific conditions, Diels–Alder
reactions are reversible. The reversible Diels–Alder reactions are called the retro–Diels–Alder
reactions. Diels–Alder ... Show more content on Helpwriting.net ...
The dienes are capable of containing various substituents. Though, Diels–Alder reactions only
proceed when dienes are in s–cis conformation. However, the Diels–Alder reactions can proceed
when the butadienes are in s–trans conformation. The dienophiles contain 'masked functionality,' for
example; the dienophiles participate in Diels–Alder reaction with the dienes inserting 'masked
functionality' onto the resultant molecule. Several reactions occur to transform this 'masked
functionality' into a suitable group. The dienophiles can take part in Diels–Alder reactions by either
'normal demand' or 'inverse demand' Diels–Alder reaction. In 'normal demand,' Diels–Alder
reactions, the dienophiles contain electron–withdrawing group conjugated to the alkenes. In inverse
demand, the electron–donating group is in conjugation with

The Reaction Of The Alcohols
The alcohols 1–propanol and 2–pentanol were converted into alkyl halides through a certain series
of steps. The first step was reflux, and the purpose of reflux is to add energy to the solution and not
lose any solution to evaporation. This energy helps initiate the acid–catalyzed dehydration reaction
and also promotes rearrangement. The next step was distillation, which functioned to separate
liquids based on boiling points. The distillation utilizes boiling points to separate the alkyl halide
products from many impurities that might exist. Reflux is the first step instead of distillation because
refluxing allows the reaction to progress. If distillation was performed first, separation would begin
before the reaction was allowed time to ... Show more content on Helpwriting.net ...
For example, since the voltage adapter connected to the sand bath may not have been working
properly, inconsistent heating patterns could have proposed a problem during reflux. Also, a few
extra drops of water may have invaded the product while the flask was cooling in the ice bath during
distillation. Furthermore, it is possible that not all of the organic layer was drained out of the
separatory funnel during separation, and maybe the drying agent was not allowed enough time to
remove all of the water. Errors will always hinder the success of a reaction, which will greatly effect
the percent yield.
Infrared spectroscopy (IR) is a very useful tool that can read a molecule's functional groups from a
small sample. By monitoring the disappearance and appearance of certain groups, it is possible to
confirm wether compounds have formed. In this experiment, for example, the reactants are alcohols,
whose IRs will show a large and broad absorption around 3500 cm–1. These hydroxide groups are
eventually replaced during the reactions, and the final products will not contain any hydroxides.
Therefore, the IR of the products will not show the large and broad hydroxide absorption.
Monitoring the disappearance of the hydroxide stretch will allow the reaction progression to be
monitored also. The complete disappearance of this stretch will confirm that a new product has been
formed. However, IR

Alkyne Diphenylacetylene Lab Report
Dehydrobromination 5. Introduction In this experiment, an alkyne–diphenylacetylene–was prepared
by a double dehydrobromination. Potassium hydroxide (KOH) and high heat were used to
accomplish this. The precipitate of this reaction was collected by vacuum filtration. It was then
washed with water and recrystallized using ethanol. The product was then isolated again before the
weight was taken for further analysis of percent yield. The melting point was also taken to identify
that it was the desired product. 6. Data and Results The product of this experiment had a melting
point of 58–60 °C and a weight of .014 g. Calculations showed that the limiting reagent was meso–
stilbene dibromide. With that and the weight of the product, the percent ... Show more content on
Helpwriting.net ...
These triple bonds are created by overlapping two pairs of p–orbitals that create a right angle on
adjacent sp–hybridized carbon atoms. Two successive elimination reactions are used to prepare
alkynes in a manner like the creation of double bonds. The first elimination reaction produces a
double bond and the second creates the triple bond. These reactions are done using a strong base and
heat. The triple bonds of the alkynes are subject to electrophilic additions reactions. Electrophilic
reagents, or Lewis acids, can easily react with the pi–electrons of the triple bond, which act as a
Lewis base. An equivalent amount of a halogen or hydrogen halide can be added to produce a
double bond and a second equivalent amount can be added to create a saturated product. In this
experiment, meso–stilbene dibromide was used to produce diphenylacetylene through two
sequential dehydrohalogenations. The first part is a concerted E2 mechanism, where the reactant is
deprotonated at the beta carbon from the halide ion that will be leaving. This creates a transition
state where the leaving hydrogen and halide are anti–periplanar with each other, meaning that they
are at a 180° angle in relation to one another. This reaction is caused by a base–in this case,
potassium hydroxide–and produces a haloalkene, or vinyl halide. Potassium hydroxide was only
added to reaction when needed, as

Wittig Reaction Lab Report
Chapter Two – Results and Discussion 2.1 Synthesis of 1,3–butadienes 1,3–butadienes can be
synthesised from aldehydes and ketones using the Wittig reaction. The Wittig reaction facilitates the
synthesis of new carbon–carbon double bonds at specific locations in aldehydes and ketones
(Bernard & Ford, 1983). The overall reaction mechanism is shown in Figure 4. Figure 4. The Wittig
Reaction – Formation of a transitional oxaphosphetane and resultant formation of a new carbon–
carbon alkene bond resulting in the synthesis of 1,3–butadienes from aldehydes and ketones.
Protocols for synthesising 1,3–butadienes from aldehydes and ketones have been established in the
literature. The synthesis protocol identified by Greatrex et al. (2014) was ... Show more content on
Helpwriting.net ...
034 100 5% 6 2.947 0.707 17 4% a) Yield determined by purity determined from 1H NMR spectrum
analysis following isolation by column chromatography. Table 4 –Summary of 1,2–dioxines
synthesis reaction outcomes The general approach involved transforming each of the 1,3–butadienes
at the site of the terminal alkene bond via reaction with the singlet oxygen. Meso–
tetraphenylporphyrin was used as the photosensitiser to generate the singlet oxygen. The prepared
butadienes were added to a volume of dichloromethane and cooled using a water–cooled jacketed
flask. Reactions were followed by TLC and reaction times varied for each reaction based on
observations. Reactions were ceased on the basis of an increasing prevalence of a new product
appearing at the baseline of the TLC. Products of the reactions were purified via column
chromatography. Two cycloaddition products were observed in each reaction. These were the 1,2–
dioxine resulting from the Diels–Alder [4+2] cycloaddition reaction, and an aldehyde resulting from
the ene cycloaddition

Experiment 5 : The Bomination Of An Alkene
Introduction Experiment 5 deals with the bromination of an alkene. It is considered an addition
reaction in which bromine is added to an alkene. This breaks double bonds of alkene and forms an
alkane. With the removal of the double bond, each bromine atom can now attach to a carbon. In the
first part of this experiment, bromine is added to the π bond of trans–stilbene, which results in the
formation of vicinal dibromide. Vicinal is a term used to describe two functional groups bonded to
two neighboring carbon atoms. It is important to note that in this addition reaction, the electron–rich
alkene acts as the nucleophile and bromine as the electrophile. As shown above, acetic acid is used
to dissolve the alkene. Molecular bromine is considered to be highly toxic and corrosive. With that
in mind, pyridinium tribromide is used as an alternative due to the fact it's safer and easier to
manage.
Bromination of an alkene can give different products. The two bromine atoms can be attached to the
double bond in two possible ways, either syn or anti. The product has two chirality centres and may
obtain four possible stereoisomers:
A B C D Experiment 7 introduces the concept of "dehydrohalogenation". The idea is that alkyl
halides may undergo elimination reactions which involve Brønsted–Lowry bases. In this event, a
halide anion and a proton are lost to form a new π bond. There are two common types of elimination
reactions: either unimolecular (E¬1) (the rate determing step) or bimolecular (E2). E1 elimination
reaction is a two step mechanism which requires the formation of a carbonium ion intermediate by
the splitting of the leaving group (the halide in this case). After this formation, a loss of a proton
(H+) causes a π bond to form. We want the the carbonium ion to be as stable as possible. This
ensures that it forms easily as well as increases the rate of the E1 reaction. On the other hand, E2
elimination reactions are a one step mechanism in which a simultaneous removal of a proton by the
base leads to the loss of the leaving group, thus generating a new π bond. In this part of the
experiment,

Dimethyl Fumarate Lab
Conclusion:
The isomerization of dimethyl maleate to dimethyl fumarate experiment was successful in that it
occurred to completion under the correct conditions. Only the predicted set of conditions allowed
for isomerization of dimethyl maleate to dimethyl fumarate, a test tube of dimethyl maleate and
bromine placed under an intense light source. The other two test tubes did not isomerize as one did
not contain the bromine, so there was no ability to form a radical, and the other was placed in the
dark so it did not have the ability to initiate the radical formation of bromine. It is unlikely any error
occured with the exception of the possibility that there was a very slight amount of isomerization
that occurs in the test tube that was placed ... Show more content on Helpwriting.net ...
The reaction is assumed to have gone to completion as the bromine was not apparent as indicated
due to the lack of an orange color in the test tube and radical reactions propagate and allow for the
reaction to run to completion producing pure dimethyl fumarate. The fact that this is a radical
reaction also explains why the bromine molecule is not added to the double bond, because the
bromine radical is terminated after the double bond is reformed. The carvone experiment was
carried out successfully as both enantiomers were put into a polarimeter and the direction and angle
that they rotate plane polarized light in. This allows for quantitative explanation of why R and S
isomers are designated as rotating in the left or right direction (+ or –). Their was a slight variance in
the magnitude of the angle, as they should both be equal, however it is possible that temperature or
concentration of the samples contributed to this error. The qualitative analysis was successful in that
both the R and S enantiomers of the carvone oils displayed a distinctive, yet similar smell, thus
displaying that some enantiomers will have distinguishable odors. Therefore, smell is a possible way
to separate certain enantiomers as opposed to spending thousands of dollars on special gas
chromatography equipment to determine the identity

Diels-Alder Reaction Lab
In this paper, the four Diels–Alder reactions observed in lab will be analyzed in terms of their
mechanisms and experimental procedures. Through the Diels–Alder reaction, four different products
were formed: dimethyl tetraphenyl phthalate, hexaphenylbenzene, tetraphenylnaphthalene, and
triptycene. The general Diels–Alder rules and patterns were followed for each reaction, however,
certain things such as solvents and experimental methods were changed in accordance to
compounds in order to allow the Diels–Alder reactions to fully and wholly occur. The Diels–Alder
reaction was discovered by Otto Diels and Kurt Alder in 1928. They discovered the mechanism
through which cyclohexane, a six–membered ring, could be formed. During a Diels–Alder reaction,
three pi bonds are broken to form two new sigma bonds and one new pi bond. As shown in Figure 1,
a general Diels–Alder reaction, this breaking and forming of new bonds happens simultaneously.
Although Diels and Alder first introduced their work in 1928, it was not until 1950 that they
received the Novel Prize for Chemistry as recognition. ... Show more content on Helpwriting.net ...
Although the diene and dienophile can be in either cis and trans confirmations, it is preferred that
the diene exist in cis–confirmation because of its ability to react with the dienophile. If the diene
was in trans–confirmation, the carbons would be too far apart to react, thus not yielding a reaction.
Therefore, if the diene in a reaction is in trans–confirmation to being with, it needs to be switched to
a cis–confirmation in order to even obtain a reaction at

Alkenes from Alcohols: Cyclohexene from Cyclohexanol
I. Objectives * Be able to prepare cyclohexene from the dehydration of cyclohexanol * Understand
the mechanisms of the dehydration reaction (acid–catalyzed dehydration). * Know how to use the
necessary equipment for this reaction, such as the fractioning column. * Obtain positive results in
unsaturation tests for the presence of carbon–carbon double bond (cyclohexene).
II. Background
Cyclohexanol, the reagent of this experiment, is used in the production of nylon, paints, plastics,
detergents, textiles and pesticides. The dehydration of cyclohexanol to cyclohexene can be
accomplished by pyrolysis of the cyclic secondary alcohol with an acid catalyst at a moderate
temperature or by distillation over ... Show more content on Helpwriting.net ...
X. Results * After distillation the product was divided into two test tubes: One adding Br2 and the
other one KMnO4 * Both test resulted in a colorless liquid, meaning a positive result for carbon–
carbon double bond presence (cyclohexene).
Test 1: Addition of Br2:
Test 2: Addition of KMnO4:
* Both tests resulted in a colorless liquid, giving positive results for carbon–carbon double bond
presence (cyclohexene).
XI. Discussion/ Conclusion
An alcohol can be dehydrated to form an alkene in the presence of a strong acid. We used 85%
phosphoric acid and the alcohol is cyclohexanol. The reaction is carried out in a fractional
distillation apparatus. As the alcohol and acid are heated, alkene and water are produced and
distilled into a collection vial. The distillation process was long and we needed to be careful to not
get any other product that cyclohexene; that is, we had to observe temperature changes, so the
temperature would not affect the product yield. The distillation was continued until the temperature
rose well over the boiling point of cyclohexene. At this point we assumed that the product has
distilled into the collection vial.
To test our product for the presence of cyclohexene in the product, we

Diels-Alder Reaction Lab Report
Introduction: The process of synthesizing cyclic compounds is a common task presented in the field
of organic chemistry. The Diels–Alder reaction consists of a conjugated diene bonding with an
alkene in which two new σ bonds are formed and two π bonds are broken, yielding a cyclohexane
product1. This type of reaction is useful in the field for several reasons; the reaction produces a high
yield, produces two new stereocenters, and is stereospecific1. For a diene to participate in the
reaction, two conditions must be met. The diene's double bonds have to be conjugated and in the s–
cis conformation2. If a bicyclic product is desired a cyclic diene can be used1. This reaction results
in the formation of a six–membered ring3. Diels–Alder reactions ... Show more content on
Helpwriting.net ...
Xylene was found to be a good solvent for this reaction because of its low freezing point and high
boiling point2. The endo– stereoisomer was the major product because it contains the most overlap
between π bonds. The efficiency of this reaction was found by calculating the % yield of the final
product. The % yield of the Diels–Alder reaction was 31.55%. The observed melting point was
261.5–262°C which is close enough to the literature value of, 262–264 °C to be considered a pure
product. Over all it can be concluded that the Diels–Alder reaction performed yielded a pure
product, but failed to produce a high %

Lab Report 7: Dehydration, Bromination And Hydration
Lab Report 7: Dehydration, Bromination and Hydration
Ethan O'Leary
CM 244
Segment 40
Walk 8, 2018
Presentation:
For this test, it was broken into three separate examinations. The investigations contained:
dehydrohalogenation, bromination and corrosive catalyzed hydration. All together for these
responses to happen, they need to respond with alkenes. Alkenes are natural exacerbates that have a
carbon–carbon twofold bond as the useful gathering for that compound. The best approach to get a
carbon–carbon twofold out of an atom if isn't as of now display is the utilization of alkyl halides and
alcohols. The response between an alkyl halide and a liquor that delivers a carbon–carbon P bond is
called a disposal response.
To expand more ... Show more content on Helpwriting.net ...
Next, the layer was dried with anhydrous sodium sulfate and exchanged to round base flagon to set
up for basic refining. The round base jar is discharged out and set up for sublimation. As a result of
the choking of time, the blend was not ready to sufficiently warm to get a nice sum on the tube to
gather for weight and dissolving point. Along these lines, I was not ready to inspire enough to finish
dissolving point. The softening point was taken from somebody in lab whose dissolving point was
between 88–100°C. The measure of grams recouped was .07g. That is a modest number which
prompts a low percent yield and is expected to not having the capacity to warm for a drawn out
stretch of time because of the test being longer than

Elimination Reactions
In this lab, the goal is to explore the idea of elimination reactions and investigate ways to
synthesizes alkynes. The product that will be produced is diphenylacetylene and this will be done by
starting with meso–stilbene dibromide using elimination reactions. The balanced reaction is:
For an E2 reaction to occur, strong bases should be utilized for this lab since E2 reactions favor well
with strong bases. KOH is a strong base that is also acts as a strong nucleophile. This is because it
contains a hydroxyl group and they are both strong bases and nucleophiles.
Heat will also be applied to encourage the chemicals to go through the elimination reaction. There
will be two ways to apply heat so that the reaction can occur. The first way is through a thermal
reaction process using sand baths to heat the reaction. The other method of heating is to microwave
the product so that the elimination reaction can ... Show more content on Helpwriting.net ...
A flea stir bar and 4.0 mL of 95% ethanol were added to the microwave reactor vessel. The solution
was then stirred using a magnetic stirrer until all the KOH dissolved. 1.0 g of meso–stilbene
dibromide was added in the microwave reactor vessel. The cap of the vessel was placed, tightened
and the vessel was placed in a microwave reactor carousel. After the reaction was complete, the
vessel with the mixed reaction was placed in a tap water bath so that it may be cooled. After it
cooled down, 10 mL of DI water was placed in a 50 mL and the reaction mixture was poured into
there to precipitate the product. The product was then collected by vacuum filtration and Hirsch
funnel. The product was rinsed with 3 mL of DI water three times. The product dried on the filter
paper with the vacuum on for 5 minutes after the rinse. The product was then placed in a drawer so
that it may completely dry so that the weight and the melting point may be recorded later. The final
product was a light brown

Advantages Of Olefins
Olefins are usually produced in large quantities in the petrochemical industry. The separation of
olefins from paraffins is of primary importance to the chemical industry. Olefin/paraffin mixture is
difficult to separate due to their similar physical and chemical properties such as molecular sizes and
boiling point. The most common method for olefin/paraffin separation in the industry is the
distillation process, commonly known as cryogenic distillation which is considered as one of the
most energy–intensive processes in the oil and gas industry [1]. Due to the high costs and energy
consuming associated with this distillation an alternative methods need to be used.
Silver salts have been used as a separation facilitator since 1944. In this early work, an aqueous
solution of the silver salt AgNO3 at 50 wt% was used in the absorption and extraction of light
olefins from ... Show more content on Helpwriting.net ...
In addition, the formed complex is chemically reversible, and therefore easy to break with a
relatively small amount of energy. The advantage of this operation is the lower energy requirement
for the separation as the break of the complex can be done by using simple engineering operations,
such as heating or de–pressurization [4, 5]. Hollow fiber membrane contactors have been considered
as an alternative mean for gas/ liquid separation which have many advantages over conventional
direct gas/ liquid techniques such as spray towers and packed/tray columns [6]. In this process, two
phases gas phase and an absorbent solvent come into direct contact for mass transfer without the
dispersion of one phase into the other due to the presence of the

Addition Of Bromine To Alkene
In this experiment, the addition of Bromine to an alkene was done. In doing so the solution
undergoes a halogen addition reaction, which is a simple reaction where a halogen molecule is
added to a double bonded carbon0carbon alkene functional group. In this experiment cholesterol
(the alkene used) is dissolved in 2 mL of methyl tert–butyl ether and Bromine (halogen) is added to
the solution to create a reaction. To proceed in the reaction Bromine, reddish–brown, solution is
added into a solution of the cholesterol and MTBE solution. After that is done, the solution is mixed
by swirling the flask around until getting a persistent light yellow colored solution, if not retrieved
more Bromine should be added. This solution is then cooled to form crystals, while the solution
cools a wash solution was made to wash the solution of cholesterol bromine when being filtered.
This wash is made of 1.4 mL HOAc (glacial acetic acid), and 2 mL of methyl tert–butyl ether. When
the solution is cooled it is to be filtered by vacuuming, when pouring the solution into the funnel, the
reaction vial was washed with the wash solution that was made. This is done to make sure you are
recovering all of the crystals in your solution. When the vacuuming is all set the crystals were left
out to dry for a week and the mass and melting point were retrieved. This type of reaction that
happened is a halogenation and an electrophilic addition reaction, which is a halogen addition
reaction. In this case,

Bromination Of Alkene Lab Report
For this experiment, an addition mechanism for the bromination of an alkene was observed along
with studying chirality. The bromination of the substituted alkenes was known as an oxidation
reaction and it produced different stereoisomers based on the alkene's geometry. The E–stilbene
when exposed to bromine produced dibromostilbene. Three products can potentially form from this
reaction which are meso, D, and L stilbene bromide. The goal of this experiment was to identify
which stereoisomer predominated in the reaction and determine the most favored cation
intermediate. The first step of the mechanism was to break the alkene pi bond and form a new C–Br
bond. When the alkene broke, a secondary carbocation formed. The bromide anion attached to ...
Show more content on Helpwriting.net ...
In a round bottom flask, both the E–stilbene and the DCM were added along with a rice stir bar.
When stirring the solution containing the bromine, it is safer to place a keck clamp on the top of the
round bottom flask and rest the stopper on top, so no solution flies out of the round bottom flask.
This prevents sealing to occur and protects against bromine exposure. Sealing is dangerous because
DCM is a high vapor pressure and if the system is sealed then this can lead to a pressurized system
which is not safe. The stir bar was used to dissolve the solid. Then bromine was also added to the
solution. Then the solution was stirred once more for ten to fifteen minutes or until the orange color
had mostly disappeared and a white solid had formed in a colorless solution. After this, the
precipitate product was isolated and filtered by using a Buchner funnel and was washed with cold
DCM to ensure the removal of most of the bromine and any unreacted starting material as well as
most of the D/L isomer. Once the product has dried, the weight of the product was recorded and the
percent yield. The melting point was also taken to ensure that all of the unreacted starting material
along with the D/L isomers had been removed from the

The Synthesis Of 13 Butadienes
CHAPTER TWO RESULTS AND DISCUSSION
2.1 Synthesis of 1,3–butadienes
Dienes can be synthesised from aldehydes and ketones using the Wittig reaction. The Wittig reaction
facilitates the synthesis of new carbon–carbon double bonds at specific locations in aldehydes and
ketones (Bernard & Ford, 1983). The overall reaction mechanism is shown in Figure 1.
Protocols for synthesising 1,3–butadienes from aldehydes and ketones have been established in the
literature. The synthesis protocol proposed by Greatrex et al. (2014) was used and reactions using
several aldehydes (cinnamaldehyde, piperonaldehyde, and 2–chloro–benzaldehyde) were
successfully performed to synthesise the required butadienes 1, 2, and 3, Scheme 2.
The general approach involved transforming the aldehydes at the site of the carbonyl group. Use of
an appropriate triphenylphosphonium halide (methyl for cinnamaldehyde, and allyl for piperonal
and 2–chloro–benzaldehyde) afforded the correct 1,3–butadiene. Deprotonation of the
triphenylphosphonium halide was achieved using potassium tert–butoxide reacted under an
atmosphere of nitrogen. An observable colour change was observed on addition of the
triphenylphosphonium halide to the solvent, and subsequently on the addition of an aldehyde.
Reactions were followed by thin liquid chromatography (TLC), and the butadienes were purified via
chromatography (1 and 2 via column chromatography, and 3 via dry flash chromatography). Both
the e– and z– isomers of the butadienes

Structure Elucidation
Keghan
Chapter 8
MULTIPLE CHOICE QUESTIONS
Topic: Structure Elucidation
1. An alkene adds hydrogen in the presence of a catalyst to give 3,4–dimethylhexane.
Ozonolysis of the alkene followed by treatment with zinc and acetic acid gives a single organic
product. The structure of the alkene is:
CH3
A)
CH3CH=C–CHCH2CH3
(cis or trans)
CH3
CH3
B)
CH3CH2C=CCH3
(cis or trans)
CH2CH3
C)
CH3
CH2=CCH2CHCH2CH3
CH3
CH2
D)
CH3CH2CCHCH2CH3

CH3
CH3
E)
CH3CH2CHCHCH=CH2
CH3
Ans: B
241
Keghan
Chapter 8
2. Ozonolysis of compound Z yields the products shown below. What is the structure of Z?
O
Z
1) O3
2) Zn, HOAc
O
2HCH + CH3CCH2CH
O
I
II ... Show more content on Helpwriting.net ...
A)
B)
C)
D)
E)
i. O3 ii. Zn, HOAc
H
O
+

4–Hexen–1–yne
3–methyl–1–hexene
(E)–2–hexene
(Z)–2–hexene
4–methyl–1–hexene
Ans: E r 247
H
O
Keghan
Chapter 8
12. Which alkene would yield only CH3CH2COOH on oxidation with hot alkaline potassium
permanganate (followed by acid work–up)?
A) (E)–2–hexene
B) (Z)–2–hexene
C) 2–methyl–2–pentene
D) (E)–3–hexene
E) (E)–4–methyl–2–pentene
Ans: D
13. An unknown compound, B, has the molecular formula C7H12. On catalytic hydrogenation 1 mol
of B absorbs 2 mol of hydrogen and yields 2–methylhexane. B has significant IR absorption band at
about 3300 and 2200 cm–1. Which compound best represents B?
A) 3–methyl–1–hexyne
B) 5–methyl–2–hexyne
C) 5–methyl–1,3–hexadiene
D) 5–methyl–1–hexyne
E) 2–methyl–1,5–hexadiene
Ans: D
14. What compound would yield an equimolar mixture of CH3CH2CH2CHO and CH3CHO upon
treatment with O3, followed by Zn/HOAc?
A) 1–Hexene
B) cis–2–Hexene
C) trans–2–Hexene
D) More than one of these
E) None of these
Ans: D
15. An alkene with the molecular formula C8H16 undergoes ozonolysis to yield a mixture of
(CH3)2C=O and (CH3)3CCHO. The alkene is:
A) 2,2–Dimethyl–2–hexene

B) 2,3–Dimethyl–2–hexene
C) 2,4–Dimethyl–2–hexene
D) 2,4,4–Trimethyl–2–pentene
E) More than one of the above is a possible answer.
Ans: D
248
Keghan
Chapter 8

2-Methylcyclohexanol Molecules
INTRODUCTION: The polymerization of sugar molecules, such as sucrose and fructose, involves
the dehydration of two sugar monomers to produce a peptide C=O bond, and the release of water.
This common biomolecular mechanism has been greatly studied within the science disciplines. For
Biologists, they've studied how nature does it, and for Chemist, they've studied how we mimic, and
manipulate it. Chemist refer to such chemical reactions, in which atoms or groups of atoms are
removed from a molecule, as an elimination. Elimination reactions are very common in organic
chemistry. Examples include the dehydration of alcohols and the dehydrohalogenation of alkyl
halides. The dehydration of alcohols is the method most frequently used in the laboratory ... Show
more content on Helpwriting.net ...
Using the formation of a tosylate to transform the OH group of the starting material into a good
leaving group so that it could be eliminated in the formation of a carbon–carbon double bond. As
illustrated in the results of the GC, IR, and NMR analysis of the products, the experiment was
successful and occurred as predicted. It can be concluded that if a specific product is desired from
experimental synthesis, the best option, in terms of control and specificity, is to design an
experiment that favors an E2 mechanism. As it proves to be the more selective of the
elimination/substitution

Alkyl Halide Lab
Elimination Reactions of Alkyl Halides Purpose The purpose of this lab is to understand the process
of eliminating an alkyl halide to form an alkene. The experiment is carried out by first converting
the alcohol, 2–methy–2–butanol, into the alkyl halide of 2–chloro–2–methylbutane that will then be
put through dehydrohalogenation that favors elimination reaction (E2) to create a mixture of 2–
methyl–2–butene by alcoholic potassium hydroxide (KOH⁻) base and 2–methyl–1–butene by
potassium tert–Butoxide (Kt–BuO⁻) base. A fractional distillation will be taken to purify the mixture
and an additional gas chromatography will be done to further analyze the mixture composition. A
bromide test will be done to determine the production of an alkene in the ... Show more content on
Helpwriting.net ...
The group decide to carry out the elimination reaction with alcoholic potassium hydroxide. A dry
100 milliliter round–bottom flask was filled with 5 grams of potassium hydroxide and 50 milliliters
of absolute ethanol. The flask was stoppered and swirled for no more than 10 minutes to have the
potassium hydroxide mostly dissolved. Then 5.3 grams of the 2–chloro–2–methylbutane was added
along with a stir bar. A fractional distillation was set up to run the reaction. A Hempel column served
first as a reflux condenser while the elimination reaction was carried out. The Hempel column was
attached with the round–bottom flask while being lubricated with silicone grease to not allow the
joints to freeze. Water hoses were attached to the Hempel column and water was circulated from
bottom to top during the reflux period. An additional rubber hoses were connected to the vacuum
adapter that was also attached to the receiving flask (50 milliliter round–bottom flask). The reaction
was heated for 30 minutes for a gentle reflux. A tan Variac was set to 55 (rate of heating) to allow
for the vapor condensation front to be about half–way up the Hempel column. After the reflux
period, then distillation was started by connecting the water hose on the vacuum adapter to the water
to circulate during the fractional distillation. The distillation was run until

Diels-Alder Reaction Lab
[4+2] Cycloaddition:
The Diels–Alder Reaction
Brittany Patmon
Procedures completed with:
Ahria Rachell, Cody Leonard, and Luke Harrison
TA: Joseph Osazee
April 10, 2016 Abstract:
Introduction:
In 1950, Otto Diels and Kurt Alder, a research student under Diels, were awarded the Nobel Prize in
Chemistry for their work on the discovery of a reaction that is commonly practiced still to this day1.
The reaction that is presently known as Diels–Alder reaction involves dienes reacting with alkenes
to form cyclic compounds1. Diels–Alder reactions are among the most resourceful in organic
synthesis due to the fact that they are relatively simple to carry out, produce a high amount of
product, and the compounds produced are highly stereo–specific2. The ... Show more content on
Helpwriting.net ...
The solution was subsequently arranged into a reflux apparatus which included a wet paper towel in
order to prevent vapor loss. The solution was refluxed at a temperature ranging from 180°C–185°C
for thirty minutes via sand bath. The contents of the micro–test tube were then cooled to room
temperature followed by an ice bath in order for crystals to form. The crystals were then collected
via suction filtration using a Hirsch funnel. The product was washed with ice–cold xylene (3

Iodoform Test Lab Report
The identification and characterization of the structures of unknown substances are an important
part of Organic Chemistry. In this experiment a sample of an unknown aldehyde or ketone was
obtained. From this sample two solid derivatives were prepared. Their melting points were obtained
and compared to those listed in the Table of Aldehyde & Ketone Derivatives. From this the
unknown sample was identified. As additional aid a Benedict's test and Iodoform test were used.
These are functional group tests used for distinguishing between aldehydes, ketones and methyl
ketones. A Benedict's test tests positive for aliphatic aldehydes and negative for aromatic aldehydes
and ketones. An Iodoform test tests positive for methyl ketones and acetaldehyde ... Show more
This was accomplished through functional group tests, preparation of two solid derivatives and
determining their melting points and making careful observations. The unknown sample was
determined to be cinnamaldehyde due to the odor it produced when the various tests were
performed. Even though the melting points obtained from the Dinitrophenylhydrazone and
Semicarbazone derivatives were not close to the melting points of cinnamaldehyde (255℃ and
215℃ respectively) the odor gave a clue to the unknown compound. The melting point differences
could have been due to human error handling the glassware and following the lab manual
instructions.
Synthesis/

Diels-Alder Reaction Lab Report
Within this experiment a type of cycloaddition reaction was performed, called Diels–Alder reaction.
This type of reaction involves both a 1,3–diene and an alkene, called the dienophile in this reaction.
Within this reaction two new sigma bonds were formed at the 1 and 4 carbon atoms of the diene.
Two other pi bonds are also formed simultaneously with the sigma bonds. Due to this concerted
nature of the reaction the diene must be able to adopt a s–cis configuration, making the reaction
stereospecific. The new carbon sima bonds would occur in the same face of the diene and
dienophile, making the reaction a syn–addition reaction. For this reaction 3–sulfolene was
decomposed into the needed 1,3–butadiene. This diene then proceeded to react with ... Show more
The product that was obtained from the experiment was analyzed by weighing the product,
obtaining melting point range and an IR spectrum. An NMR spectrum was unable to be obtained.
The mass of the product was .4162 grams, with a precent yield of 17.34%. The low percent yield
can be The melting point range that is expected from 4–cyclohexene–cis–dicarboxylic anhydride is
101–103°C. The actual range that was obtained from the melting point test was 82.9–93.2°C. This
range is quite a bit lower than the expected value. Not only is the value under the expected range,
but it is also a large range. This would indicate an impure product. The melting point range is much
higher than the melting range of the reactants, indicating that a reaction did occurred. By analyzing
the IR spectrum that was obtained, all of the structural units that expected to be in 4–cyclohexene–
cis–dicarboxylic anhydride are present. There was an C–C double bond, as indicated by the peak at
about 1609 cm–1. Sp3 C–H was also present as indicated from the peaks in the 3000cm–1 to
2850cm–1 region. The C–O bond of an ester is present, as indicated from the 1266cm–1 peak. From
analyzing both the

Alkite Synthesis

Recommended

Recommended

More Related Content

More from Amanda Reed

More from Amanda Reed (20)

Recently uploaded

Recently uploaded (20)

Alkite Synthesis