Organic Chemistry : Organic Chemistry

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #1 : Carbonyl Products

Consider the following reaction.

Vt orgo 12 19 15Problem 1 product

In this reaction, two molecules of an alpha-hydroxy acid are condensed with heat to form product. What functional group is created in this reaction?

Possible Answers:

Aldehyde

Ether

Ester

Ketone

Correct answer:

Ester

Explanation:

For this question, we're shown the structures of both the reactants and products, and we're asked to identify which functional group is in the product.

First, let's go through the answer choices and define them. Then, we'll compare that definition with what we see in the product.

Aldehydes are functional groups in which a carbon atom is double bonded to an oxygen atom. The carbon atom must also be bound to at least one hydrogen atom, and to another hydrogen or carbon atom. Usually, aldehydes occur at the terminal ends of a molecule.

Ketones are similar to aldehydes. These functional groups contain a carbon atom double bound to an oxygen atom. In addition, the carbon atom is bound to two other carbon atoms. Thus, ketones tend to be found within a compound, as opposed to at the terminal ends.

Ethers are a class of functional group in which an oxygen atom is situated between two carbon atoms via a single bond.

Carboxylic acids are a functional group in which a carbon is double bound to one oxygen atom, and also single bonded to the oxygen of a hydroxyl group. This functional group does not occur in the product, but it does occur in the reactant.

Esters are a functional group in which a carbon atom is double bonded to an oxygen atom, and also single bonded to another oxygen atom. However, unlike carboxylic acids, esters do not contain a hydroxyl group. Instead, the oxygen atom is bound to another "R group," typically another carbon atom.

Now, let's go ahead and take a look at the product. Shown in red circles, we see that there are two ester groups in the product. Thus, the ester functional group is the correct answer.

Problem 1 product answer

Example Question #1 : Carboxylic Acid Chemistry

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

Possible Answers:

Correct answer:

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 or , 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.

Example Question #621 : Organic Chemistry

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

Possible Answers:

Pentanal

2-methylpentan-2-ol

1-pentanol

2-pentanol

2-pentanone

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.

Example Question #621 : Organic Chemistry

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

Possible Answers:

malonic ester

3-ethylheptanoic acid

None of the other answers

nonanoic acid

a ten-carbon ketone

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.

Example Question #622 : Organic Chemistry

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

Possible Answers:

Aldehyde

Amide

All of these are carboxylic acid derivatives

Ester

Correct answer:

Aldehyde

Explanation:

Aldehyde is not a derivative of carboxylic acid. Esters can be derived from carboxylic acids by reacting them with  to form an acid chloride. From there, react it with an  to form an ester. Amides can be derived from carboxylic acids by reacting them with  to form an acid chloride. From there, react it with  to form an amide.

Example Question #623 : Organic Chemistry

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

Possible Answers:

All of these

Correct answer:

Explanation:

As a general rule, any carboxylic acid derivative can be converted into al carboxylic acid when reacting with 

Example Question #624 : Organic Chemistry

Noname01

What is the product of the given reaction?

Possible Answers:

5

Noname01

Noname02

Noname01

3

Correct answer:

Noname01

Explanation:

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

Example Question #2 : 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:

 (cold and dilute)

 and 

PCC

Correct answer:

Explanation:

 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.

Example Question #1 : Mechanisms And Intermediates

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

Possible Answers:

Hexylcyclohexane

1-hexylcyclohexanol

2-hexylcyclohexanol

Cyclohexane

3-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 #625 : Organic Chemistry

2butanone

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

Possible Answers:

1-butanol

No reaction will occur

2-butanone

2-butanol

1-butanone

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.

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