Carbonyl Reactions

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Organic Chemistry › Carbonyl Reactions

Questions 1 - 10
1

What is the product of the following reaction?

Image13

and

Explanation

The reaction uses a Grignard reagent's nucleophilic carbon to attack the carbon in carbon dioxide. Following treatment with water the resulting molecule (a carboxylate anion, of the form ) the carboxylate oxygen will be protonated, and the result is a carboxylic acid. Thus, the resulting molecule is a benzene ring with a carboxyl group attached (this is also known as benzoic acid).

2

What is the product of the following reaction?

Image13

and

Explanation

The reaction uses a Grignard reagent's nucleophilic carbon to attack the carbon in carbon dioxide. Following treatment with water the resulting molecule (a carboxylate anion, of the form ) the carboxylate oxygen will be protonated, and the result is a carboxylic acid. Thus, the resulting molecule is a benzene ring with a carboxyl group attached (this is also known as benzoic acid).

3

Esterification

What is the product of this reaction?

Ester

2

3

6

2butanone

Explanation

This is a classic esterification reaction. Esterfication occurs when a carboxylic acid and an alcohol are reacted together. Only one answer choice is an ester.

4

Esterification

What is the product of this reaction?

Ester

2

3

6

2butanone

Explanation

This is a classic esterification reaction. Esterfication occurs when a carboxylic acid and an alcohol are reacted together. Only one answer choice is an ester.

5

What is the final organic product of the reaction shown?

Screen shot 2015 11 14 at 11.07.54 am

Screen shot 2015 11 14 at 11.04.22 am

III

I

II

IV

V

Explanation

First step: esterification

Second step: reduction

Third step: neutralization

Fourth step: oxidation to aldehyde

Fifth step: alkene metathesis

6

What is the final organic product of the reaction shown?

Screen shot 2015 11 14 at 11.07.54 am

Screen shot 2015 11 14 at 11.04.22 am

III

I

II

IV

V

Explanation

First step: esterification

Second step: reduction

Third step: neutralization

Fourth step: oxidation to aldehyde

Fifth step: alkene metathesis

7

Screen shot 2015 07 07 at 8.30.46 pm

Determine the major product of the given intramolecular aldol reaction.

Screen shot 2015 07 07 at 8.30.53 pm

II

I

III

IV

None of these

Explanation

Keep in mind the following principles: Cyclization is favored when a five/six-member ring may be formed. Addition at an aldehyde is favored relative to the same reaction at a ketone.

As a result, abstraction of a hydrogen bound to carbon 6 (an alpha-carbon) is favored since the resulting carbanion may attack the aldehyde (carbon 1) to form a six-member ring, resulting in compound II. Compound I results from abstracting a hydrogen from carbon 2, generating a carbanion which may then attack the ketone. Based on the latter of the above principles, this is a minor product.

8

What is the product of the reaction shown?

Screen shot 2015 11 15 at 12.19.05 pm

Screen shot 2015 11 15 at 12.19.15 pm

IV

I

II

III

V

Explanation

First step: bromination across the double bond

Second step: double dehydrohalogenation and removal of terminal alkyne hydrogen

Third step: neutralization of the molecule

Fourth/fifth step: hydroboration/oxidation, followed by keto/enol tautomerization

9

Screen shot 2015 07 07 at 8.30.46 pm

Determine the major product of the given intramolecular aldol reaction.

Screen shot 2015 07 07 at 8.30.53 pm

II

I

III

IV

None of these

Explanation

Keep in mind the following principles: Cyclization is favored when a five/six-member ring may be formed. Addition at an aldehyde is favored relative to the same reaction at a ketone.

As a result, abstraction of a hydrogen bound to carbon 6 (an alpha-carbon) is favored since the resulting carbanion may attack the aldehyde (carbon 1) to form a six-member ring, resulting in compound II. Compound I results from abstracting a hydrogen from carbon 2, generating a carbanion which may then attack the ketone. Based on the latter of the above principles, this is a minor product.

10

What is the product of the reaction shown?

Screen shot 2015 11 15 at 12.19.05 pm

Screen shot 2015 11 15 at 12.19.15 pm

IV

I

II

III

V

Explanation

First step: bromination across the double bond

Second step: double dehydrohalogenation and removal of terminal alkyne hydrogen

Third step: neutralization of the molecule

Fourth/fifth step: hydroboration/oxidation, followed by keto/enol tautomerization

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