Which of the following is not chiral?
- 2-Hydroxypropanoic acid
- 2-Butanol
- 2,3-Dibromopentane
- 3-Bromopentane
Answer
(4) 3-Bromopentane
Solution
A molecule with a carbon atom attached to four different groups (chiral carbon) and no element of symmetry is chiral.
(1) CH3-CH(OH)-COOH: C-2 has H, OH, CH3, COOH ⇒ chiral.
(2) CH3-CH(OH)-CH2-CH3: C-2 has H, OH, CH3, C2H5 ⇒ chiral.
(3) CH3-CHBr-CHBr-CH2-CH3: C-2 and C-3 are two different chiral centres ⇒ chiral.
(4) CH3-CH2-CHBr-CH2-CH3: C-3 carries two identical ethyl groups ⇒ no chiral carbon ⇒ not chiral.
Answer: (4)