Organic Chemistry : Help with Alcohol Synthesis

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #12 : Carbonyl Products

What is the product of a hydroboration–oxidation reaction with 1-hexylcyclohexene?

Possible Answers:

3-hexylcyclohexanol

Cyclohexane

2-hexylcyclohexanol

Hexylcyclohexane

1-hexylcyclohexanol

Correct answer:

2-hexylcyclohexanol

Explanation:

This reaction is an electrophilic addition reaction with an alkene. This is one of many alkene addition reactions that can add an -OH group onto your starting material. The key aspect of an hydroboration-oxidation reaction is the anti-Markovinikov addition to the double bond. The -OH group should be on the least substituted of the two carbons that originate from the double bond. In light of this information, the answer is 2-cyclohexanol.

Example Question #1 : Help With Alcohol Synthesis

2butanone

What is the product when the given starting compound is reacted with lithium aluminum hydride and acid?

Possible Answers:

1-butanol

2-butanone

No reaction will occur

1-butanone

2-butanol

Correct answer:

2-butanol

Explanation:

This reaction involves a very strong reducing agent in lithium aluminum hydride, . LAH converts ketones, aldehydes, esters, and acid chlorides into alcohols. This reaction changes the carbonyl group into a hydroxyl group. As a result, the final answer is 2-butanol.

Example Question #13 : Carbonyl Products

What reagents are required to efficiently form a tertiary alcohol with two of the same substituents in only two steps?

Possible Answers:

An ester reacted with 1) 2RLi and 2) NH3

An ester reacted with 1) 2RMgBr and 2) H3O+

An ester reacted with 1) RMgBr and 2) H3O+

An ester reacted with: 1) excess ethanol and 2) H3O+

An acid chloride reacted with 1) 2RMgBr and 2) hexane

Correct answer:

An ester reacted with 1) 2RMgBr and 2) H3O+

Explanation:

This is an example of a Grignard reaction that requires the use of an ester or acid chloride, and more than one equivalent of an organometallic. The second step would be to react the product of the first step in an acidic source.

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