Chapter 16

Review questions

16.12

OH CH3
O
N
(a) * CH3 (b) *
OH

16.13
16.14 (c) and (d) have R configurations.

3
CH3 H4
(a) C 4 (b) C 3
Br H 2 CH3
1 CH2OH HOCH2 Br
2 1

S S
perspective

perspective
2
CH2OH 1 Br R
R
(c) 3 C 1 (d) 4 C 2
H3 C Br H CH2OH
H4 3 CH3

opposite perspective

16.15 (a) –H (4) –CH3 (3) –OH (1) –CH2OH (2)

(b) –CH2CH=CH2 (3) –CH=CH2 (1) –CH3 (4) –CH2COOH (2)

(c) –CH3 (3) –H (4) –COO– (2) –NH3+ (1)

(d) –CH3 (4) –CH2SH (2) –NH3+ (1) –COO– (3)

16.16 An asterisk indicates the stereocentres. There are four possible stereoisomers of 3-methyl-2-
pentanol.

OH
*
CH3CH2CHCHCH3 3-Methyl-2-pentanol
*
CH3

OH OH OH OH
Review problems

16.28 (a) alkane

or
* *

(b) alcohol

OH

(c) aldehyde

O
*
H

(d) ketone

*
O

(e) carboxylic acid

OH
*
O

16.29 There are eight alcohols with the formula C5H12O, of which three are chiral. The carbon
stereocentres are indicated with an asterisk.

OH OH OH
OH
* *

Chiral Chiral
 OH
* OH
OH OH

Chiral

16.31

16.32 Structures (a) through (d) and (f) are the stereo-representations of (S)-lactic acid.
Structures (e), (g), and (h) are stereo-representations of (R)-lactic acid and therefore, are
enantiomers of structure (a).

COOH CH3 COOH CH3

(a) C (b) C (c) C (d) C
H HO HO H COOH
OH H CH3
CH3 HOOC H HO
S S S S

COOH CH3 OH CH3

(e) H C OH (f) H C OH (g) H3C C COOH (h) H C COOH
CH3 R S COOH H R OH R