Carbonyl Products

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Organic Chemistry › Carbonyl Products

Questions 1 - 10
1

Noname01

What is the product of the given reaction?

Noname01

3

5

Noname01

Noname02

Explanation

The hydrolyzation of a nitrile with hydronium leads to a carboxylic acid. Only one choice is a carboxylic acid.

2

Noname01

What is the product of the given reaction?

Noname01

3

5

Noname01

Noname02

Explanation

The hydrolyzation of a nitrile with hydronium leads to a carboxylic acid. Only one choice is a carboxylic acid.

3

Noname01

What is the product of the given reaction?

Noname01

Noname02

Noname03

Noname01

Noname02

Explanation

This question tests knowledge on carboxylic acid derivatives and the formation of the carboxylic acid derivatives. , or thionyl chloride, reacts with a carboxylic acid to form an acid chloride. The choice that replaces the with a . The reaction also expels .

4

Noname01

What is the product of the given reaction?

Noname01

Noname02

Noname03

Noname01

Noname02

Explanation

This question tests knowledge on carboxylic acid derivatives and the formation of the carboxylic acid derivatives. , or thionyl chloride, reacts with a carboxylic acid to form an acid chloride. The choice that replaces the with a . The reaction also expels .

5

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

2-hexylcyclohexanol

1-hexylcyclohexanol

3-hexylcyclohexanol

Hexylcyclohexane

Cyclohexane

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.

6

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

2-hexylcyclohexanol

1-hexylcyclohexanol

3-hexylcyclohexanol

Hexylcyclohexane

Cyclohexane

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.

7

Which combination of starting material and reagent will produce the product shown?

Screen shot 2015 11 15 at 11.19.43 am

5-hydroxyvaleric acid and

Pentanedioic acid and

4-hydroxybutyric acid and

4-hydroxybutyric acid and

5-hydroxyvaleric acid and

Explanation

5-hydroxyvaleric acid (5-hydroxypentanoic acid) is a five-carbon carboxylic acid alcohol and will produce the required lactone. This reaction is typically acid-catalyzed. Pentanedioic acid (glutaric acid) is a linear dicarboxylic acid, 4-hydroxybutyric acid only has four carbons and will not produce the desired product without being modified.

8

Which combination of starting material and reagent will produce the product shown?

Screen shot 2015 11 15 at 11.19.43 am

5-hydroxyvaleric acid and

Pentanedioic acid and

4-hydroxybutyric acid and

4-hydroxybutyric acid and

5-hydroxyvaleric acid and

Explanation

5-hydroxyvaleric acid (5-hydroxypentanoic acid) is a five-carbon carboxylic acid alcohol and will produce the required lactone. This reaction is typically acid-catalyzed. Pentanedioic acid (glutaric acid) is a linear dicarboxylic acid, 4-hydroxybutyric acid only has four carbons and will not produce the desired product without being modified.

9

An organic chemist wants to synthesize an ether product. She begins with methanol and ethanol as her substrates. How would she go about synthesizing the desired ether product?

Convert the alcohol on the methanol to a tosylate group and allow this modified substrate to react with the ethanol

It is impossible to create an ether product with these substrates

Put both substrates in an aprotic solvent and allow them to react via

Add heat to the substrates to elicit a dehydration reaction

Explanation

The substrates must be modified in order to attain the desired product. In order to get the desired product, she needs to change one of the alcohol groups into a good leaving group. One way to do this is to react the methanol with to create a primary tosylate. Because of its advanced resonance, tosylate is an extraordinary leaving group, and so the ethanol is free to attack the modified substrate to form an ether.

10

An organic chemist wants to synthesize an ether product. She begins with methanol and ethanol as her substrates. How would she go about synthesizing the desired ether product?

Convert the alcohol on the methanol to a tosylate group and allow this modified substrate to react with the ethanol

It is impossible to create an ether product with these substrates

Put both substrates in an aprotic solvent and allow them to react via

Add heat to the substrates to elicit a dehydration reaction

Explanation

The substrates must be modified in order to attain the desired product. In order to get the desired product, she needs to change one of the alcohol groups into a good leaving group. One way to do this is to react the methanol with to create a primary tosylate. Because of its advanced resonance, tosylate is an extraordinary leaving group, and so the ethanol is free to attack the modified substrate to form an ether.

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