The document discusses three isomers - carvone, limonene, and thymol. Each molecule has an enantiomer where the mirror image has the same molecular formula but a different arrangement, producing different smells, tastes, and reactions. Limonene has the molecular formula C10H16 and gives oranges their scent. Its enantiomer L-limonene smells like pine needles. Thymol has the molecular formula C10H14O and forms colorless to white crystals with antimicrobial properties. It is isomeric to carvacrol from oregano oil.

1. Comparing Carvone, Limonene, And Thymol
The word Isomer is derived from the Greek words isos meaning "equal", and méros meaning "part"
(1). Isomers are compounds that have the same molecular formula, but they are arranged differently
in space. This makes each arrangement have its own unique properties. These molecules are
considered mirror images of one another and yet produce completely different smells, tastes, and
reactions. I am going to discuss three isomers I have in my kitchen every day. These are Carvone,
Limonene, and Thymol. Each of these molecules has an enantiomer where its mirror image has the
same molecular formula yet when arranged differently they produce something different.
To begin let us look at Limonene. Limonene has the molecular formula C10H16. The IUPAC name
for Limonene is 1–methyl–4–prop–1–en–2–ylcyclohexene (2). Limonene has the molecular weight
of 136.238 g/mol (2). D–Limonene is naturally occurring oil in orange peels. D–Limonene gives us
the sweet orangey scent of oranges. Yet its enantiomer the L– Limonene molecule gives us a slight
lemon scent, but is often thought to smell like pine needles or turpentine (3). Limonene appears as a
clear liquid (2). D and L– Limonene have a chiral carbon on carbon number four of the cyclohexene
ring (4). Limonene enantiomers are ... Show more content on Helpwriting.net ...
Thymol has the molecular formula C10H14O and the IUPAC name 5–Isopropyl–2–methylphenol
(9). It also has the molecular weight 150.221g/mol (9). Thymol is isomeric to Carvacrol, which is oil
of oregano (Origanum Vulgare). Notice that Thymol and Carvacrol have the same molecular
formula as Carvone, but because Carvone is not a phenol like Thymol and Carvacrol they have
completely different scents (8). Thymol forms colorless to white crystals (9). Thymol has a methyl
group off carbon number three and Carvacrol the methyl group comes off carbon number two. These
enantiomers both have medicinal purposes as they have great antimicrobial properties
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3. Mat 540 Final
Optimize the molecular geometry of a water molecule (H2O) at HF/STO–3G level of theory in
Gaussian–09 through the GaussView Visualization software package on the desktops provided.
Give optimized bond length lengths and angles using this combination of methods and basis set.
Ans. Bond Length = 0.98927 Å and the Bond Angle H–O–H is 100.035 degrees
Recalculate the geometry using an alternative method of your own choice.
Ans. Using Semi–empirical (PM6) we get a bond length of 0.94911 Å and a Bond Angle H–O–H is
107.488 degrees.
Give molecular orbital diagram with drawings of the molecular orbitals. You may have to rerun the
calculation with pop=full included.
¬Ans. Molecular orbitals for isolated H–O–H molecule were calculated using ... Show more content
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Draw the dipole moment of the chair and boat configuration. Which of those structures will dissolve
better in water and why?
Ans. Chair conformer of cyclohexane has negligible dipole moment due to symmetry and equal
charge distribution. On the other hand Boat conformation of cyclohexane has dipole moment due to
the shape of the conformer making it polar due to charge distribution and steric effects. BOAT
CONFORMER (Note: – Grey spheres are C atoms and Blue spheres are H atoms)
Hence the boat conformer is able to dissolve in water but stabilizes soon and turns into the chair
conformer making it non–polar and separating it from water.
How many different configurations of Fluoro–cyclohexane exist? Draw structures but do not
minimize in Gaussian.
Ans. Dipole moments of Fluoro–Cyclohexane have increased by a factor of 611.6 as compared to
cyclohexane.
This explains how the presence of a single fluoride atom instead of a hydrogen impacts the structure
and charge distribution of the cyclic hydrocarbon. In turn adding a Fluoride atom also increases the
energy of the cyclic hydrocarbon creating less stable structures in boat, twist and half chair
increasing ΔG and decreasing the amount of other conformers in a solution compared to chair.

4. ... Get more on HelpWriting.net ...

6. The Reduction Of 4 Tert ¬ -butylcyclohaxanone
In this experiment, the reduction of 4–tert¬–butylcyclohaxanone was performed using sodium
borohydride. To complete this reduction, 0.5010 g of 4–tert¬–butylcyclohaxanone was added to 6.0
mL of methanol and heated until the ketone dissolved completely. Next, 0.0510 g of sodium
borohydride was added to the solution. At this time, bubbles formed and an exothermic reaction
took place. After the solution was stirred for 20 minutes, 2 mL of sulfuric acid was added to the
flask. The solution became white and cloudy, and more bubbles formed. Immediately after the acid
was added, 5 mL of water was also put into the reaction flask. The solution was stirred for 10
minutes. During this time, a white solid formed. After this, the solution was ... Show more content
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This was calculated by taking the mass of 4–tert¬–butylcyclohaxanol, dividing it by the theoretical
yield determined by mass of the limiting reagent, 4–tert¬–butylcyclohaxanone, and multiplying by
100. This percent yield is respectable, but a higher one could have been obtained. A source of error
resulting in a lower percent yield was the filtering to remove the magnesium sulfate out of the dried
organic solution. When filtering, some of the liquid was absorbed into the filter paper, prohibiting
some of the product from being recovered. To prevent this loss, one should use a pipet to recover the
product from the magnesium sulfate. The product that was recovered during this experiment, was
spectroscopically analyzed, and a ratio of cis–trans product was found. IR and 1H NMR analysis
was also performed for the starting ketone, 4–tert¬–butylcyclohaxanone. The IR spectra, RM–07–
Oi, contained peaks at 2947 cm–1, 2868 cm–1, 1720 cm–1, and 1365 cm–1. These peaks represent a
carbon–hydrogen stretch, a sp3 hybridized carbon, a ketone and a ring carbon–carbon stretch, which
are all present in 4–tert¬–butylcyclohaxanone. This confirms that the initial ketone used was 4–
tert¬–butylcyclohaxanone. The 1H NMR also proves this. Peaks found at 2.34 ppm, 2.07 ppm, 1.45
ppm and 0.87 ppm show that only four chemical shifts occur in this compound. There are not four
types of hydrogens in this molecule, but some chemical environments are similar resulting in only
four
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8. Confferences: The Difference Between Structural And...
Isomers are different organic compounds with the same molecular formula but differ in their
properties. Isomers are divided into structural and stereoisomers. Structural isomers are isomers that
have the same molecular formula but differ in structural formula, that is, in the order in which the
different atoms are linked in the molecules. They have different IUPAC names, the same or different
functional groups, different physical properties and different chemical properties. Structural isomers
are further divided into chain isomerism, position isomerism, functional isomerism, metamerism and
tautomerism. [1]
Chain isomerism is isomers that have the same molecular formula but differ in which the carbon
atoms are bonded to each other. For example, ... Show more content on Helpwriting.net ...
This isomerism is caused by migration of H–atom from one group to another. For example, ethyl
acetoacetate is in equilibrium mixture of the following two forms:
Conformational isomers differ in the relative position of some of the atoms in the molecule in
3Dimensional–space due to the rotation about sigma bonds.
Configurational isomers are those isomers which arise due to some kind of rigidity in the molecule,
and these are inter converted only by bond breaking or making. Configurational isomerism has been
further classified in two types, geometric isomers and optical isomers.
Geometric isomers (or cis–trans isomers) are molecules with a double bond that form cis and trans
isomers. Square planar molecules can also display geometric isomerism. Cis and trans refer to the
orientation of functional groups within a molecule and mostly occur in alkenes. In alkenes, C=C
bonds have restricted rotation so the groups on either end of the bond are 'frozen' in one position; it
isn't easy to flip between the two. This produces two possibilities. The two structures cannot
interchange easily so the atoms in the two molecules occupy different positions in
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10. Advantages And Disadvantages Of Cyclohexane
In cyclohexane, there are two identical chair conformers and cyclohexane has the hydrogen atoms
located as the axial and equatorial like what had mentioned at the previous topic. The chair
conformers are presents in equal concentration due to the rapid interconversion of the axial groups
and equatorial groups. When cyclohexane bears a substituent, the two chair conformers become
different to one another as in one conformation, the substituent will locate at the axial location while
in the other conformation, the substituent locate at the equatorial location. Compare the axial and
equatorial, the substituent group tends to favour the equatorial location because there are presents of
steric hindrance in the axial location. Mono–substituted ... Show more content on Helpwriting.net ...
Let's take dimethylcyclohexane as an example. Dimethylcyclohexane have two methyl groups
bonded to the cyclohexane. Below is the simple planar structure of several dimethylcyclohexane. In
1,1–dimethylcyclohexane conformers, the methyl groups must sit on the axial and equatorial
position each regardless of which chair conformer is considered. Since the methyl groups are the
same in 1,1–dimethylcyclohexane, the two chair conformers are identical to each other and their
present is in equal concentration. 1,2–, 1,3– and 1,4– dimethylcyclohexane, the analysis of
conformation is more complex. It may involve the cis–trans relationships depends on the relative
location of the methyl groups. As we count the carbons on the ring in chair conformation, from
carbon number one to six, the uppermost bonds on each carbon will change its orientation from
equatorial to axial and back. This is the alternate pattern of bonds on a given side of a chair–ring
conformation. In 1,2–dimethylcyclohexane, if it is a trans isomer, the two methyl groups must locate
in the equatorial position while if it is a cis isomer, the two methyl groups locate in the equatorial
and axial position each. Therefore, the trans–1,2–dimethylcyclohexane is more stable than the
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12. Importance of Steriochemistry
ASSIGNMENT ON
PHARMACEUTICAL IMPORTANCE OF STEREOCHEMISTRY
PREPARED FOR: Nowshin Nowaz Rumzhum Lecturer, Dept. of pharmacy Stamford University
Bangladesh
PREPARED BY: Md. Wahid Rezwan ID No: BPH02805674 Batch No: 28th D
STAMFORD UNIVERSITY BANGLADESH
Introduction: Stereochemistry may seem like a trivial subject because differences between
stereoisomers are usually subtle. In nature, however, and most importantly, in biological systems
such as the human body, these subtle differences have sweeping implications. Most drugs for
example, are often ... Show more content on Helpwriting.net ...
CHIRALITY AND ENANTIOMERS:
This section contains the basics needed to understand chiral drugs. Undergraduate textbooks in
chemistry are good resources for a more thorough discussion of chirality and enantiomers. The most
important point is that chiral drugs have 2 structurally similar forms that can behave very differently
in biological systems due to their different shapes in 3–dimensional space. These 2 possible form
sare termed enantiomers, and the 2 enantiomers of a given chiral drug should be considered 2
different drugs. This topic is discussed further in the next section. each chiral center. Optical rotation
is often used because it is easier to determine experimentally than absolute configuration,but it does
not provide information about the absolute configuration of an enantiomer. For a given enantiomer
pair, one enantiomer can be designated (+) andthe other as (–) on the basis of the direction they
rotate polarized light. Optical rotations have also been described as dextrorotatory for (+) and
levorotatory for (–). Racemates can be designated as (R,S) or (±).
CHIRAL DRUGS IN BIOLOGICAL FIELDS:
Chiral drug have identical physical and chemical properties in an achiral environment. In a chiral
environment, one enantiomer may display different chemical and pharmacologic behavior than
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14. Isomerization: A Chemical Composition
Isomerization is the chemical process by which a compound is transferred into any of its isomeric
forms. i.e., forms with the same chemical composition but with different structure or configuration
and, hence, generally with different physical and chemical properties. An example is the conversion
of butane, a hydrocarbon with four carbon atoms joined in a straight chain and is a branched–chain
isomer, isobutane, by heating the butane to 100° C or higher in the presence of a catalyst. Butane
and isobutane have widely different properties. Butane boils at –0.5° C and freezes at –138.3° C,
whereas isobutane boils at –11.7° C and freezes at –159.6° C. The isomerization of straight–chain
hydrocarbons to their corresponding branched–chain isomers is an important step (called reforming)
in gasoline manufacture.
There are two general types of isomers. Constitutional isomers or structural isomers are compounds
with the same molecular formula, same number of atoms but do not have the same connectivity
between them. For example the following molecules have the same molecular formula but different
connectivity. Image
There are four main types of structural isomers. They are known as position isomer, chain isomer,
functional group isomers and tautomers. Chain isomers is a type of molecular isomerism seen in
carbon compounds; as the number of carbon atoms in the molecule increases, the linkage between
the atoms may be a straight
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16. Nitro vs nitrito linkage isomers Essay
Abstract
In this experiment, the nature of linkage isomers will be observed on the example of
nitritopentaamminecobalt(III) Chloride and nitropentaamminecobalt(III) Chloride. Their relative
stability will be compared on standard conditions and the infrared spectroscopy of both the isomers
will be obtained to analyze the characteristic absorption bands for the nitro and nitrito group. Yield
for nitritopentamminecobalt(III) Chloride was obtained to be = 1.9221 g(73.24 %) and yield for
nitropentamminecobalt(III) Chloride = 0.76 g(76 %)
Introduction
Linkage isomers may arise when one or more of the ligands can coordinate to the metal ion in more
than one way. The first reported example of linkage ... Show more content on Helpwriting.net ...
A portion of the nitrito complex was placed in the oven at 110 degrees Celsius and was left for a
week. The product was observed to have dark green color and the infrared spectrum was obtained
for this compound as well using KBr pellets.
Results
Theoretical yield calculations
For [Co(ONO)(NH3)5]Cl2
[CoCl(NH3)5]Cl2 + NaNO2 = [Co(ONO)(NH3)5]Cl2 + NaCl (eqn 1.4) n([CoCl(NH3)5]Cl2) =
2.518 g / 250.4456 = 0.010054 mol n(NaNO2) = 2.5 g / 68.99 = 0.03624 mol
Thus, [CoCl(NH3)5]Cl2 is the limiting agent. n([CoCl(NH3)5]Cl2) = n([Co(ONO)(NH3)5]Cl2) =
0.010054 mol m([Co(ONO)(NH3)5]Cl2) = 0.010054 mol * 260.998 = 2.62407 g
%Yield = 1.9221 g / 2.62407 g = 73.24 %
For [Co(NO2)(NH3)5Cl2
[Co(ONO)(NH3)5]Cl2 = [Co(ONO)(NH3)5]Cl2 (eqn 1.5)
Their molecular weight is same so
% Yield = 0.76 g / 1 g = 76 %
Infrared spectrum table
Table : Absorption bands of the products synthesized
Compound name
Peak(cm–1)
Peak assignment
Literature reference (cm–1)
Chloropentaamminecobalt(III) Chloride

17. 3300.42 (s)
Vas(NH3)
3267 1
3171.33(s)
Vs(NH3)
3174 1
1588.97(m)
Vas(NH3) degenerate
1589 1
1308.34(s)
Vs(NH3) angle deformation
1309 1
859.46(s) ρr(NH3) 850 1
499.027
Vs(Co–N)
485 1
Nitropentaamminecobalt(III) Chloride
3214.3(s)
Vas(NH3)
3200 1
1617(s)
V(as(NH3) degenerate
1615 1
1435.7(s)
Vas(NO2) scissoring
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