This document provides answers to questions about organic chemistry concepts related to carboxylic acids and their derivatives. Key points covered include:
- Carboxylic acids can form hydrogen bonds to themselves and water, giving them higher boiling points than alcohols.
- During acid-base reactions of carboxylic acids, the acid ionizes in water to form carboxylate and hydronium ions.
- Acyl halides readily react with water via hydrolysis to form the corresponding carboxylic acid and hydrogen halide gas.
1 Question 1 (Alcohols and Carbonyl Compounds - 20 marks.docxjoyjonna282
1
Question 1 (Alcohols and Carbonyl Compounds - 20 marks)
(a) Why does hexan-2-one have a lower boiling point than hexan-2-ol?
O OH
(2)
(b) Dehydration of the compound below in acid gives mainly one product. Suggest, with a
reason, what would be the major product.
H
+
heatOH .
(1)
(c) Esters are known for their very pleasant fragrances. The aroma is dependent on the
starting materials used to prepare the ester. Give the original starting materials used to
produce the ester below.
O
O
(2)
(d) The substitution reaction between the alkyl halide below and water results in an alcohol.
2
(i) Show the full mechanism of the reaction as it occurs via an SN1 pathway. Identify
all the elements of the reaction.
(5)
(ii) Which factor can be investigated to determine if the reaction proceeds by a
unimolecular or bimolecular mechanism, and how is it relevant in terms of the
mechanism?
(2)
(iii) Explain briefly whether the chlorine analogue of the substrate would react faster
or slower than the given compound above.
(2)
(iv) Draw a fully labeled energy profile for this SN1 reaction.
(4)
3
Question 2 (Saccharides - Total 14 marks)
(a) Below is the Fischer projection of a sugar.
CHO
HHO
OHH
OHH
HHO
CH2OH
(i) Show a Haworth projection of the cyclic form of the sugar, identifying the
anomeric centre as either or .
(2)
(ii) Fully classify the saccharide above in terms of its optical rotation, carbon skeleton
and class.
(2)
(iii) When the compound is reduced with NaBH4, is the product optically active or
not? Explain your answer.
(2)
(b) What is the process called when the optical rotation of an aqueous solution of a pure
anomer of glucose changes with time? Use chemical structures to demonstrate what is
happening.
(3)
4
(c) The following question relates to the structure below:
A. B.
C.
O
HO
HO
OH
O
OH
O
HO
OH
O
HO
OH
O
O
HO2C
OH OH
(i) Use arrows to identify the glycoside links between sugars a and b as well as b and
c and name them appropriately.
(3)
(ii) Explain if this is a reducing sugar or not.
(2)
5
Question 3 (Amines and Amides - Total 11 marks)
(a) Briefly explain why amines have lower boiling points than amides of similar molecular
weight.
(2)
(b) (i) What is the name of the following amine?
N
(1)
(ii) What is the structure of 2,2-dimethylpentanamine?
(1)
(c) Give the outcome of the reactions below.
(i) Ph-NH2 + CH3-CO2H
(1)
(ii)
H3O
+
N
H
O
(2)
(d) The structure of N-methylpropanamide is given below.
N
H
O
Predict the solubility of N-methylpropanamide by showing the full extent of H-
bonding between the compound and water.
(2)
6
(e) Explain with refe ...
1 Question 1 (Alcohols and Carbonyl Compounds - 20 marks.docxjoyjonna282
1
Question 1 (Alcohols and Carbonyl Compounds - 20 marks)
(a) Why does hexan-2-one have a lower boiling point than hexan-2-ol?
O OH
(2)
(b) Dehydration of the compound below in acid gives mainly one product. Suggest, with a
reason, what would be the major product.
H
+
heatOH .
(1)
(c) Esters are known for their very pleasant fragrances. The aroma is dependent on the
starting materials used to prepare the ester. Give the original starting materials used to
produce the ester below.
O
O
(2)
(d) The substitution reaction between the alkyl halide below and water results in an alcohol.
2
(i) Show the full mechanism of the reaction as it occurs via an SN1 pathway. Identify
all the elements of the reaction.
(5)
(ii) Which factor can be investigated to determine if the reaction proceeds by a
unimolecular or bimolecular mechanism, and how is it relevant in terms of the
mechanism?
(2)
(iii) Explain briefly whether the chlorine analogue of the substrate would react faster
or slower than the given compound above.
(2)
(iv) Draw a fully labeled energy profile for this SN1 reaction.
(4)
3
Question 2 (Saccharides - Total 14 marks)
(a) Below is the Fischer projection of a sugar.
CHO
HHO
OHH
OHH
HHO
CH2OH
(i) Show a Haworth projection of the cyclic form of the sugar, identifying the
anomeric centre as either or .
(2)
(ii) Fully classify the saccharide above in terms of its optical rotation, carbon skeleton
and class.
(2)
(iii) When the compound is reduced with NaBH4, is the product optically active or
not? Explain your answer.
(2)
(b) What is the process called when the optical rotation of an aqueous solution of a pure
anomer of glucose changes with time? Use chemical structures to demonstrate what is
happening.
(3)
4
(c) The following question relates to the structure below:
A. B.
C.
O
HO
HO
OH
O
OH
O
HO
OH
O
HO
OH
O
O
HO2C
OH OH
(i) Use arrows to identify the glycoside links between sugars a and b as well as b and
c and name them appropriately.
(3)
(ii) Explain if this is a reducing sugar or not.
(2)
5
Question 3 (Amines and Amides - Total 11 marks)
(a) Briefly explain why amines have lower boiling points than amides of similar molecular
weight.
(2)
(b) (i) What is the name of the following amine?
N
(1)
(ii) What is the structure of 2,2-dimethylpentanamine?
(1)
(c) Give the outcome of the reactions below.
(i) Ph-NH2 + CH3-CO2H
(1)
(ii)
H3O
+
N
H
O
(2)
(d) The structure of N-methylpropanamide is given below.
N
H
O
Predict the solubility of N-methylpropanamide by showing the full extent of H-
bonding between the compound and water.
(2)
6
(e) Explain with refe ...
Alcohol, phenol, ether are classes of organic compounds which find wide usage in a broad range of industries as well as for domestic purposes. Alcohol is formed when a saturated carbon atom is bonded to a hydroxyl (-OH) group. Phenol is formed when a hydrogen atom in a benzene molecule is replaced by the -OH group.
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Chem 3.5 answers #8
1. CHEMISTRY 3.5 ANSWERS
WORKSHEET EIGHT ORGANIC CHEMISTRY
Carboxylic acids and their derivatives #1
1. (a) Octanoic acid (b) Propanoic acid
2. (a) HCOOH (b) CH3CH2CH2COOH
3. Carboxylic acids have the ability to form hydrogen bonds to themselves and
also to water molecules. This means that they have high boiling points and are
soluble in water. Their boiling points are higher than alcohols because they
have two oxygen atoms in each molecule and are therefore able to make two
hydrogen bonds between each pair of molecules (dimerize). Alcohols can
make only one hydrogen bond per molecule.
4. (a) CH3COOH(aq) + H2O(l) CH3COO-(aq) + H3O+(aq)
(b) Weak acid
(c) The magnesium ribbon would react slowly with the acid forming
magnesium ethanoate and bubbles of hydrogen gas.
2CH3COOH(aq) + Mg(s) (CH3COO)2Mg (aq) + H2(g)
(d) CH3COOH(aq) + NH4OH(aq) CH3COONH4 (aq) + H2O(l)
5. (a) Condensation/ esterification
(b) The sulfuric acid acts as a catalyst and a dehydrating agent. As a
catalyst it speeds up the reaction. As a dehydrating agent it removes
water from the right hand side of the equilibrium favouring the
production of the ester.
(c) CH3COOH + CH3CH2CH2OH CH3COOCH2CH2CH3 + H2O
O O
6. (a) CH3 - C (b) CH3 -CH2-CH2-C
O-Cl O-Cl
7. In moist air the acyl halides react readily with water to hydrolyse into the acid
and HCl. The HCl gas forms visible fumes.
