Faculty of Engineering

Department of Chemical, Metallurgical and Materials engineering

ORH115B-2023 B MEMO 16 OCTOBER 2023

TUTORIAL TOPICS: ALCOHOLS, ETHERS, ALDEHYDES & KETONES, AND

CARBOXYLIC ACID & THEIR DERIVATIVES

QUESTION 1 NOMENCLATURE AND STEREOCHEMISTRY

1.1 Give the IUPAC names or structures of the following compounds. Indicate
the stereochemistry where applicable.

(a) (3)

(1S,2R)-2-hydroxycyclohexanecarbonitrile

(b) sec-butoxycyclobutane (3)

(c) (3)

(3R,4E,6S,7Z)-6-hydroxy-3-methylnona-4,7-dienoic acid
(d) (3)

3-amino-7-bromocyclooctanecarbaldehyde

(e) (3)

N-cyclopentyl-N-isopropylbutyramide

(f) (3)

(E)-cyclopropyl hex-3-en-5-ynoate

(g)

(3S,6S)-6-phenylnonan-3-ol

(h) (2S,4S)-4-bromo-4-phenylbutane-1,2-diol (3)

(i) (3)

(1R,3R)-3-bromo-2,4,7-trimethylcyclooctanamine

(j) (4)

4-bromocyclopenta-1,3-dienecarboxylic acid
(k) (2)

acetic cyclopropanecarboxylic anhydride

(l) (3)

7-(sec-butyl)-4-oxocyclohept-1-enecarboxylic acid
(m) (3)

(S)-5-bromo-N-ethyl-N-methyl-4-oxohexanamide
QUESTION 2 ILLUSTRATIONS AND DEFINITIONS

2.1 Give an example to illustrate the following terms or expressions

(d) E1 Elimination of a C6H13Cl (3)

(f) An acetal formation (2)

(e) A reaction of an alcohol with sodium hydride followed by an alkyl halide. (2)

William ether synthesis

(f) Diastereomers (2)

(g) Meso Compound of C4H8Br2 (2)

(h) Oxidation of a secondary alcohol with a strong oxidizing agenT (2)

(i) Ability of a compound to rotate plane polarised light (2)

Optical activity

(j) Formation of an ester from the reaction of an alcohol and carboxylic acid in the
presence of a catalyst. (2)

Fischer esterification

QUESTION 3 REACTIONS, REGIOSELECTIVITY AND STEREOCHEMISTRY

3.1 Predict the products, reagents or starting material of the following

reactions, indicate the stereochemistry where applicable:

(a) (4)

(b) (3)
 (c) (3)

(d) (3)
 (e) (3)

(f) (3)

(g) (3)

(h) (3)
(i) (3)

(j) (3)

(k) (3)

(l) (3)
3.2 There is a flaw (or an error) in each of the following proposed reaction.
Make the necessary correction and support the answer.

(a) (2)

Under acidic conditions nitriles results to a carboxylic acid not an alcohol.

(b) (2)

Alkyl halide should form and not carboxylic acid.

(c) (3)

The 1⁰ and 2⁰ alkyl groups react by SN2 pathway, whereby Nu- halide ion attacks the
protonated ether at the less highly substituted site. The ether oxygen atoms stays
with more hindered alkyl group and the halide bonds with less hindered group.
(d) (2)

Reduction of carboxylic acids yields primary alcohols not aldehydes

QUESTION 4 MULTI-STEP SYNTHESES REACTIONS

4.1 Provide the mechanism reaction for E2 reactions. (6)

4.2) Propose the mechanism reaction for SN2 reactions with a C4H13Cl. (6)

4.2 Propose an efficient synthesis of the given target compound from the
provided starting material and any other necessary reagents to accomplish
your transformations.

(a) (13)
(b) (7)