(SOLVED) Organic Chemistry Chapter 18, Problem 14P
Discipline: Chemistry
Type of Paper: Question-Answer
Academic Level: Undergrad. (yrs 3-4)
Paper Format: APA
Question
Organic Chemistry
Predict the major product of the following reactions:
(a)
(b)
(c)
(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.
