(SOLVED) Organic Chemistry Chapter 18, Problem 14P

Discipline: Chemistry

Type of Paper: Question-Answer

Academic Level: Undergrad. (yrs 3-4)

Paper Format: APA

Pages: 1 Words: 275

Question

Organic Chemistry

Predict the major product of the following reactions:

(a)

(b)

(c)


Expert Solution

(a) The epoxide ring can be opened by the treatment with the base or acid. Hydroxide ion opens the epoxide ring in mechanism way from less hindered side due to strong nucleophilic nature of the hydroxide ion.

The major product of this reaction is 2-methylbutane-1,2-diol.



(b) The epoxide ring can be opened by the treatment with the base or acid. An acid opens the epoxide ring in mechanism way from more hindered side due to acid protonates epoxide oxygen and forms the partial positive charge at more hindered side which resembles like more stable carbocation.

The major product of this reaction is 2-methylbutane-1,2-diol.

(c) Grignard reagent opens the epoxide ring in mechanism way from less hindered side due to the more reactive nature of organo metallic reagents.

2-Ethyl-2,3-dimethyloxirane reacts with phenyl magnesium bromide and followed by hydrolysis to form 3-methyl-2-phenylpentan-3-ol.