Question

An alkene with the molecular formula C8H16 undergoes ozonolysis to yield a mixture of (CH3)2C=O and (CH3)3CCHO. The alkene is:

a. 2,2-Dimethyl-2-hexene.

b. 2,3-Dimethyl-2-hexene.

c. 2,4-Dimethyl-2-hexene.

d. 2,4,4-Trimethyl-2-pentene.

e. more than one of these choices is a possible answer.

Answer 1

Answer:

2,4,4-trimethyl-2-pentene yields mixture of $(CH_{3})_{2}C=O$ and $(CH_{3})_{3}CHO$

Explanation:

In ozonolysis (hydrolysis step involve a reducing agent such as Zn, $Me_{2}S$ etc.), a pi bond is broken to form ketone/aldehyde.

Ketone is formed from di-substituted side of double bond and aldehyde is formed from mono-substituted side of double bond.

Ozoznolysis involves two consecutive steps : (1) formation of ozonide, (2) hydrolysis of ozonide.

Hydrolysis can be done with/without using reducing agent. Carboxylic acid/carbon dioxide/ketone is produced when hydrolysis is done without using reducing agent.

Here, 2,4,4-trimethyl-2-pentene yields mixture of $(CH_{3})_{2}C=O$ and $(CH_{3})_{3}CHO$

Reaction steps are shown below.