Organic Chemistry : Carbonyl Reactants

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #2 : Help With Ether And Ester Reactions

Noname02

What is the product of the given reaction?

Possible Answers:

Noname04

Noname03

6

Noname01

5

Correct answer:

Noname03

Explanation:

This is a basic Claisen condensation reaction in which the  functions to take off the acidic hydrogen (between the ketone and the ester) and then the same molecule can attack a carbonyl carbon to yield Noname03.

The attack at the ester carbonyl leads to the leaving of  group.

Example Question #1 : Help With Ether And Ester Reactions

What is the product of the following reaction?

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Screen shot 2015 11 13 at 1.56.10 pm

Possible Answers:

IV only

II only

II and III

I and II

Correct answer:

II and III

Explanation:

Treatment of ethyl acetate with methoxide will yield the enolate ion (II). However, side trans-esterification reactions will also result in formation of product III.

Example Question #1 : Help With Carboxylic Acid Reactions

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Which reagent may be used to convert a carboxylic acid to an acid chloride, as shown?

Possible Answers:

Correct answer:

Explanation:

It is extremely useful in organic synthesis to utilize methods by which less reactive carboxylic acids (and their derivatives) may be converted to more reactive species, like acid chlorides. Such reactions are not always intuitive as they proceed by transforming low-energy species to more energetic states. Reagents such as thionyl chloride  and phosphorus tribromide , which you have likely seen previously in examination of common alcohol reactions, readily convert carboxylic acids to acid chlorides. The reaction is energetically favorable due to the formation of sulfur dioxide, a very stable gas.

Example Question #1 : Help With Carboxylic Acid Reactions

Which of the following is derived from a carboxylic acid?

Possible Answers:

None of these

Aldehyde

Imine

Acid anhydride

Correct answer:

Acid anhydride

Explanation:

A carboxylic acid can be synthesized directly into an acid anhydride by introducing the carboxylic acid to an acid chloride.

Example Question #2 : Help With Carboxylic Acid Reactions

Socl2 reactant

What is the major product of the given reaction?

Possible Answers:

Socl2 incorrect product

Socl2 correct product

Socl2 incorrect product 3

Socl2 incorrect product 2

Correct answer:

Socl2 correct product

Explanation:

This question is asking us to determine what the product will be when a carboxylic acid is reacted with thionyl chloride, . In this reaction, the carboxylic acid is converted into an acyl chloride, with additional production of  and  as side products. Generally, this reaction is very useful for converting carboxylic acids into a more reactive form, so that further reactions can take place.

Example Question #11 : Carbonyl Reactants

What is the product of the reaction shown?

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Possible Answers:

I

II

IV

III

Correct answer:

III

Explanation:

The Grignard reagent also acts as a base, and will remove any protons that have a low-enough pKa. This means that the alpha hydrogen will be removed, and the resulting carboxylate ion is stabilized through resonance and is unlikely to react with the protonated Grignard reagent.

Example Question #12 : Carbonyl Reactants

What is the product of the reaction below?

Image12

Possible Answers:

Correct answer:

Explanation:

This reaction is an acid-catalyzed esterification of a carboxylic acid. In the reaction the carbonyl is attacked by the alcohol oxygen, and the carbonyl is reformed by kicking off what was the hydroxyl group in the original carboxylic acid. What is left is an ester (of the form RCOOR', with R' containing the same number of carbons as was in the original alcohol).

Example Question #22 : Covalent Bonds And Hybrid Orbitals

The compound below is reacted with . What is the final hybridization around the initially chiral center carbon when the reaction is complete?

Propanol

Possible Answers:

Correct answer:

Explanation:

The initially chiral carbon has an  hybridization. Once treated with ,an oxidizing agent, the secondary alcohol in the compound is oxidized to a ketone. The central carbon is no longer a chiral center (a carbon with a double bond cannot be chiral), and the double bond (pi-bond) formed between carbon and oxygen gives the molecule an  hybridization.

 hybridization is formed with triple bonds, and an  hybridization does not exist. 

Example Question #1 : Help With Alcohol Reactions

Untitled

What is the product of the reaction when the given molecule is introduced to an acidic solution?

Possible Answers:

2-bromo-4-hexanol

None of these

3-bromo-5-hexanol

4-bromo-2-hexene

2-bromo-4-hexene

Correct answer:

4-bromo-2-hexene

Explanation:

In acidic solution, a hydrogen will be added to the hydroxy group of the given compound. This intermediate is a good leaving group. As it leaves, a hydrogen will be abstracted and a double bond will form. The bond is across carbons two and three becasue those two are more highly substituted than carbon 1, which is primary. The naming begins at the double bond, so the name is 4-bromo-2-hexene.

Example Question #53 : Reactions By Reactant

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Which reagent(s) would achieve the given synthetic transformation?

 

Possible Answers:

PCC

Correct answer:

Explanation:

Chromic acid (formed in-situ via ), the correct answer, is a powerful oxidizing agent that converts primary alcohols to carboxylic acids. PCC is also an oxidizing agent, but oxidizes primary alcohols one "rung" up the ladder to aldehydes.  and  are reducing agents, which react in the opposite direction of the given transformation.

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