Organic Chemistry : Specific Reactions and Named Reactions

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #1 : Help With Haloform Reactions

Which of the following best summarizes the haloform reaction?

Possible Answers:

A carboxylic acid reacts first with then with water

The enolate of an ester attacks another ester

An alkyl halide reacts first with the phthalimide ion, then with

The enolate of a dicarbonyl compound attacks a beta carbon of an alkene

A methyl ketone is treated with iodine and

Correct answer:

A methyl ketone is treated with iodine and

Explanation:

The haloform reaction requires a carbonyl with a terminal alpha carbon. A hydrogen gets abstracted, and the enolate is formed. A halogen attacks the alpha carbon, and the ketone is reformed. This occurs three more times until the carbon has bonds to three halogens. Then the carbon leaves, forming a carbanion, and the base attacks the carbonyl carbon. An ester is formed.

Example Question #21 : Specific Reactions And Named Reactions

Which of the following results in a single ketone product following acid catalyzed hydration?

Possible Answers:

2-decyne

5-decyne

3-decyne

4-decyne

None of these answers

Correct answer:

5-decyne

Explanation:

During acid catalyzed hydration, a hydroxy group replaces one of the bonds in the triple bond and a double bond is formed. This is called an enol. The enol naturally turns into a ketone in a process called tautomerization. The hydroxy group can attach to either carbon across the double bond, and naming is done so that substituents have the lowest numbers. Only on 5-decyne will result in a single product, as no matter which carbon the hydroxy group bonds to, it is still on carbon 5. Thus, the only final product is 5-decone.

The other answer options will still react, but will form multiple products due to lack of symmetry.

Example Question #1 : Carbonyl Reactions

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

Possible Answers:

I

III

V

II

IV

Correct answer:

IV

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

Example Question #1 : Carbonyl Reactions

What is a product when propyl-butanoate undergoes saponification?

Possible Answers:

Butyl propanoate

Propanoic acid

Butanol

None of these

Propanol

Correct answer:

Propanol

Explanation:

When naming esters, the root word in the name describes the carbon chain that carries the carbonyl. Saponification describes the breaking up of an ester. This yields an alcohol and a carboxylic acid. The chain with the carbonyl is butyl, so the carboxylic acid will be butanoic acid. That means the side with the alcohol will be propanol. 

Example Question #3 : Carbonyl Reactions

Which of the following best summarizes a Claisan condensation?

Possible Answers:

The enolate of a dicarbonyl compound attacks a beta carbon of an alkene

A methyl ketone is treated with iodine and 

A carboxylic acid reacts first with then with water

The enolate of an ester attacks another ester

An alkyl halide reacts first with the phthalimide ion, then with 

Correct answer:

The enolate of an ester attacks another ester

Explanation:

The most acidic hydrogen of the ester gets abstracted and the enolate form of the compound is attained. The electrons from the carbon-carbon double bond attack the carbonyl carbon of the other ester. Deesterfication occurs in this same step. The final product has one ketone and one ester.

Example Question #11 : Carbonyl Reactions

What is the product of the following reaction?

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Possible Answers:

 and 

Correct answer:

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).

Example Question #1 : Help With Other Named Reactions

 

 Wesag2o

Why does the reaction above require the use of Ag2O? 

Possible Answers:

The Ag2O reduces the alcohol to form the alkoxide ion

The Ag2O oxidizes the alkyl halide to form the ether

The Ag2O attacks the alcohol to form the ether

The Ag2O is an inert solvent and allows the alcohol to attack and from the product without interference

The Ag2O oxidizes the alcohol to form the alkoxide ion

Correct answer:

The Ag2O oxidizes the alcohol to form the alkoxide ion

Explanation:

The Ag2O oxidizes the alcohol to form the alkoxide ion. The Ag2O is a reducing agent, and it oxidizes the alcohol because the alcohol loses a proton. Ag2O is a strong base, meaning it will accept protons readily. The given reaction is an example of Williamson ether synthesis. This reaction occurs via an SN2 pathway. 

Example Question #1 : Help With Other Named Reactions

What is the IUPAC name of the following compound?

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Possible Answers:

None of the other answers

3-bromo-2-methylcyclohexene

6-bromo-1-methylcyclohexene

2-bromo-1-methylcyclohexene

1-bromo-2-methyl-2-cycloxene

Correct answer:

3-bromo-2-methylcyclohexene

Explanation:

The numbering of the molecule begins across the double bond and goes in the direction where the lowest numbers for substituents can be achieved. Thus, the methyl group will be on carbon two and the bromine on carbon 3. Substituents are ordered alphabetically. The base molecule is a six-membered ring with one double bond. This is called a cyclohexene.

Example Question #2 : Help With Other Named Reactions

What is the proper name of this molecule?

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Possible Answers:

None of the other answers

E-3-methyl-2-pentene

Z-2-isohexene

E-2-ethyl-2-butene

E-3-methyl-3-pentene

Correct answer:

E-3-methyl-2-pentene

Explanation:

The longest chain has five carbons and a double bond, so the base molecule is pentene. There is a methyl group on carbon 3. The double bond is between carbons two and three. The highest priority substituents are the ethyl group on one side and the methyl group on the other. One is up and one is down, so the molecule is E as opposed to Z.

Example Question #4 : Help With Other Named Reactions

Which of the following best summarizes the Michael reaction?

Possible Answers:

A methyl ketone is treated with iodine and 

An alkyl halide reacts first with the phthalimide ion, then with 

The enolate of a dicarbonyl compound attacks a beta carbon of an alkene

A carboxylic acid reacts first with then with water

The enolate of an ester attacks another ester

Correct answer:

The enolate of a dicarbonyl compound attacks a beta carbon of an alkene

Explanation:

The most acidic carbon in a dicarbonyl gets abstracted to form an enolate. The reaction involves a ketone with a double bond between the alpha and beta carbons. The carbon-carbon souble bond electrons attack the beta carbon of the alkene. At this point, the electrons from the alkene move to form a double bond between the carbonyl and alpha carbon and an enolate is fromed. The negative oxygen bonds to a hydrogen, forming the enol. Through enol-ketone tautamerization, a ketone is formed.

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