(a) Define the following:
(i) Enantiomers
(ii) Racemic mixture
(i) Enantiomers:
Enantiomers are a pair of stereoisomers that are non-superimposable mirror images of each other. They have identical physical and chemical properties except for their interaction with plane-polarized light (optical activity) and reactions with other chiral molecules. Enantiomers rotate plane-polarized light in equal magnitudes but opposite directions (one being dextrorotatory [+] and the other levorotatory [−]).
Example: The two forms of lactic acid (D-lactic acid and L-lactic acid) are enantiomers.
(ii) Racemic Mixture:
A racemic mixture (or racemate) is a 1:1 mixture of two enantiomers of a chiral molecule. Because the optical activities of the enantiomers cancel each other out, a racemic mixture is optically inactive (does not rotate plane-polarized light). Racemic mixtures are often formed in chemical reactions where a chiral product is generated from achiral reactants without the use of a chiral catalyst or enzyme.
Example: Racemic tartaric acid is an equal mixture of D-tartaric acid and L-tartaric acid.
Write IUPAC names of the following compounds and classify them into primary, secondary and tertiary amines.
(i) (CH3 )2CHNH2 (ii) CH3 (CH2 )2NH2 (iii) CH3NHCH(CH3 )2
(iv) (CH3 )3CNH2 (v) C6H5NHCH3 (vi) (CH3CH2 )2NCH3 (vii) m–BrC6H4NH2
Give one chemical test to distinguish between the following pairs of compounds.
(i) Methylamine and dimethylamine
(ii) Secondary and tertiary amines
(iii) Ethylamine and aniline
(iv) Aniline and benzylamine
(v) Aniline and N-methylaniline
Account for the following:
(i) pKb of aniline is more than that of methylamine.
(ii) Ethylamine is soluble in water whereas aniline is not.
(iii) Methylamine in water reacts with ferric chloride to precipitate hydrated ferric oxide.
(iv) Although amino group is o– and p– directing in aromatic electrophilic substitution reactions, aniline on nitration gives a substantial amount of m-nitroaniline.
(v) Aniline does not undergo Friedel-Crafts reaction.
(vi) Diazonium salts of aromatic amines are more stable than those of aliphatic amines. (vii) Gabriel phthalimide synthesis is preferred for synthesising primary amines.