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Organic Chemistry : Help with Carboxylic Acid Synthesis

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Example Questions

Example Question #23 : Reactions By Product

Which of the following reactions would NOT produce a carboxylic acid?

Possible Answers:

$CH_3CH_2CO_2Me+NaOH\rightarrow \ ?$ $\displaystyle CH_3CH_2CO_2Me+NaOH\rightarrow \ ?$

$CH_3CH_2CH_2OH+CrO_3+H_2SO_4\rightarrow \ ?$ $\displaystyle CH_3CH_2CH_2OH+CrO_3+H_2SO_4\rightarrow \ ?$

$CH_3CH_2CH_2MgBr+CO_{2(g)}\rightarrow \ ?$ $\displaystyle CH_3CH_2CH_2MgBr+CO_{2(g)}\rightarrow \ ?$

$CH_3CH_2CH_2OH+PCC\rightarrow \ ?$ $\displaystyle CH_3CH_2CH_2OH+PCC\rightarrow \ ?$

$CH_3CH_2CH_2CHO+KMnO_4\rightarrow \ ?$ $\displaystyle CH_3CH_2CH_2CHO+KMnO_4\rightarrow \ ?$

Correct answer:

$CH_3CH_2CH_2OH+PCC\rightarrow \ ?$ $\displaystyle CH_3CH_2CH_2OH+PCC\rightarrow \ ?$

Explanation:

PCC is considered a weak oxidizing agent. The reaction of a primary alcohol with PCC would only yield an aldehyde, while reaction with a secondary alcohol will yield a ketone. PCC will not be used to generate carboxylic acids.

A stronger oxidation, like KMnO_4 $\displaystyle KMnO_4$ or CrO_3 $\displaystyle CrO_3$, is required to oxidize up to the carboxylic acid. Treatment of an ester with a base or treatment of carbon dioxide with a Grignard reagent are other ways of making carboxylic acids.

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Example Question #24 : Reactions By Product

Which one of the following compounds can produce a carboxylic acid only when reacted with sodium dichromate and sulfuric acid?

Possible Answers:

2-pentanone

Pentanal

2-pentanol

2-methylpentan-2-ol

1-pentanol

Correct answer:

1-pentanol

Explanation:

After recognizing the reagents given, we know we need to begin with an alcohol. The alcohol choices differ only by how substituted they are.

For a carboxylic acid to form from a reaction with sodium dichromate and sulfuric acid, a primary alcohol needs to be available. Therefore, 1-pentanol is the correct answer.

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Example Question #25 : Reactions By Product

When 3-chloroheptane undergoes malonic ester synthesis, the final product is __________.

Possible Answers:

a ten-carbon ketone

nonanoic acid

3-ethylheptanoic acid

None of the other answers

malonic ester

Correct answer:

3-ethylheptanoic acid

Explanation:

The malonic ester is deprotonated at the most acidic hydrogen, the one on the carbon between the two oxygens. The electrons from that bond to the hydrogen form a carbon-carbon double bond while electrons from the oxygen-carbon double bond go to the oxygen atom. This is the enolate form. The chlorine leaves the 3-chloroheptane and the electrons from the carbon-carbon double bond bond to the carbon that the chlorine left. At the same time, the carbonyl is reformed. After deesterfication, 3-ethylheptanoic acid is formed.

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Example Question #26 : Reactions By Product

Which of the following is not a derivative of a carboxylic acid?

Possible Answers:

Amide

Ester

All of these are carboxylic acid derivatives

Aldehyde

Correct answer:

Aldehyde

Explanation:

Aldehyde is not a derivative of carboxylic acid. Esters can be derived from carboxylic acids by reacting them with $SOCl_{2}$ $\displaystyle SOCl_{2}$ to form an acid chloride. From there, react it with an $R'O^{-}$ $\displaystyle R'O^{-}$ to form an ester. Amides can be derived from carboxylic acids by reacting them with $SOCl_{2}$ $\displaystyle SOCl_{2}$ to form an acid chloride. From there, react it with $R_{2}N^{-}$ $\displaystyle R_{2}N^{-}$ to form an amide.

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Example Question #24 : Reactions By Product

Which of the following reagents is needed to convert an amide into a carboxylic acid?

Possible Answers:

$\displaystyle COOH/pyradine$

$H_{3}O^{+}/Heat$ $\displaystyle H_{3}O^{+}/Heat$

$\displaystyle ROH/Ether$

All of these

Correct answer:

$H_{3}O^{+}/Heat$ $\displaystyle H_{3}O^{+}/Heat$

Explanation:

As a general rule, any carboxylic acid derivative can be converted into al carboxylic acid when reacting with $H_{3}O^{+}/Heat$ $\displaystyle H_{3}O^{+}/Heat$

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Example Question #21 : Reactions By Product

Noname01

What is the product of the given reaction?

Possible Answers:

Noname01

Noname02

Noname01

Correct answer:

Noname01

Explanation:

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

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Example Question #1 : Help With Carboxylic Acid Synthesis

Please choose the best answer for the following question.

Which of the following reagents is best for converting a primary alcohol to a carboxylic acid?

Possible Answers:

$KMnO_{4}$ $\displaystyle KMnO_{4}$ (cold and dilute)

$O_{3}$ $\displaystyle O_{3}$ and DMS $\displaystyle DMS$

PCC

$K_{2}CrO_{4}$ $\displaystyle K_{2}CrO_{4}$

$LiAlH_{4}$ $\displaystyle LiAlH_{4}$

Correct answer:

$K_{2}CrO_{4}$ $\displaystyle K_{2}CrO_{4}$

Explanation:

$K_{2}CrO_{4}$ $\displaystyle K_{2}CrO_{4}$ is the only strong oxidizing agent listed. It is strong enough to oxidize the primary alcohol even further to a carboxylic acid product. The rest of the compounds listed are weak oxidizing agents or reducing agents.

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Organic Chemistry : Help with Carboxylic Acid Synthesis

Study concepts, example questions & explanations for Organic Chemistry

All Organic Chemistry Resources

Example Questions

Example Question #23 : Reactions By Product

Example Question #24 : Reactions By Product

Example Question #25 : Reactions By Product

Example Question #26 : Reactions By Product

Example Question #24 : Reactions By Product

Example Question #21 : Reactions By Product

Example Question #1 : Help With Carboxylic Acid Synthesis

All Organic Chemistry Resources

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