CHM 213 QUIZ 1

1. The nitration of methylbenzene produces mainly 2-nitromethylbenzene, whereas the

nitration of benzoic acid produces mainly 3-nitrobenzoic acid.
COOH
CH3

NO2

NO2
1-methyl-2-nitrobenzene 3-nitrobenzoic acid

Use this information to suggest suitable intermediates G and H in the following two
2-stage syntheses of bromobenzoic acids, and suggest suitable reagents for reactions I
to IV.
COOH

Br

iii
CH3 G

COOH

ii

iv
H

Br

Reagents:
reaction I .................................... reaction II .............................................

reaction III ......... .......... ………. reaction IV ..........................................

Compound G is………………….. while compound H is …………………………….

2. A compound K, C7H16O is an alcohol which is oxidized by Chromic acid to yield

compound L C7H14O. L forms crystalline DNP compound but does not form a red
precipitate with Fehling’s reagent and gives no iodoform when treated with iodine-
alkali. With the given data write all possible structures for each of compounds K and
L