Specific Reactions and Named Reactions

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Organic Chemistry › Specific Reactions and Named Reactions

Questions 1 - 10
1

What is the IUPAC name of the following compound?

Untitled

3-bromo-2-methylcyclohexene

None of the other answers

1-bromo-2-methyl-2-cycloxene

6-bromo-1-methylcyclohexene

2-bromo-1-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.

2

Screen shot 2016 01 17 at 1.46.01 pm

What is the product of the base induced chemical reaction given?

Screen shot 2016 01 17 at 1.46.07 pm

Screen shot 2016 01 17 at 1.46.20 pm

Screen shot 2016 01 17 at 1.46.24 pm

Screen shot 2016 01 17 at 1.46.29 pm

Explanation

The hydrogen bonded to the alpha carbon on carbonyl compounds is weakly acidic and when reacted with a strong base can deprotonate forming and enolate ion which has two resonance structures as shown below:

Screen shot 2016 01 17 at 1.45.50 pm

3

Screen shot 2016 01 27 at 5.53.20 pm

What is the product of the given reaction?

Screen shot 2016 01 27 at 5.53.24 pm

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Screen shot 2016 01 27 at 5.53.33 pm

Screen shot 2016 01 27 at 5.53.36 pm

Explanation

The reaction given involves the direct alkylation of a nitrile containing compound by the production of an enolate ion. The alpha hydrogen to the nitrile group which is weakly acidic can be deprotonated in the presence of a base. LDA is a mild base that converts these compounds to the enolate ion. On the last step, through nucleophilic substitution by reaction with an alkyl halide with the enolate ion yields an alkyl group in the alpha position. LDA is sterically hindered therefore allowing for the production of an enolate ion without nucleophlic addition. Similarly, an ester or ketone containing compound can also undergo this type of reaction.

Screen shot 2016 01 27 at 5.53.04 pm

4

Screen shot 2016 01 27 at 5.56.37 pm

What is the product of the given reaction?

Screen shot 2016 01 27 at 5.56.46 pm

Screen shot 2016 01 27 at 5.56.50 pm

Screen shot 2016 01 27 at 5.56.53 pm

Screen shot 2016 01 27 at 5.56.58 pm

Explanation

The reaction given involves the direct alkylation of a ketone containing compound by the production of an enolate ion. The alpha hydrogen to the ketone group which is weakly acidic can be deprotonated in the presence of a base. LDA is a mild base that converts these compounds to the enolate ion. On the last step, through nucleophilic substitution by reaction with an alkyl halide with the enolate ion yields an alkyl group in the alpha position. LDA is sterically hindered therefore allowing for the production of an enolate ion without nucleophlic addition. Similarly, an ester or nitrile containing compound can also undergo this type of reaction.

Screen shot 2016 01 27 at 5.56.25 pm

5

What is the product of the following reaction?

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and

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).

6

Screen shot 2016 01 17 at 12.54.25 pm

What is the product of the reaction given?

Screen shot 2016 01 17 at 12.59.54 pm

Screen shot 2016 01 17 at 1.00.01 pm

Screen shot 2016 01 17 at 1.00.12 pm

Screen shot 2016 01 17 at 1.00.06 pm

Explanation

In the reaction below, a ketone is protonated by a strong acid. This triggers the deprotonation of the weakly acidic hydrogen bonded to the alpha carbon by a bromide ion and formation of an alkene functional group.

Screen shot 2016 01 17 at 1.00.53 pm

7

Screen shot 2016 01 24 at 3.07.21 pm

What is the product of the chemical reaction given?

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Explanation

Claisen condensation is a reaction between two molecules containing an ester functional group. Similar to ketones and aldehydes, esters are weakly acidic because the alpha hydrogen to the carbonyl group can be deprotonated in the presence of a base. The ion that is formed nucleophilicly bonds to a second ester molecule. As seen below, an ethoxide molecule expels. Addition of an acid in the final step gives the final product.

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8

Screen shot 2016 01 17 at 12.54.25 pm

What is the product of the reaction given?

Screen shot 2016 01 17 at 12.59.54 pm

Screen shot 2016 01 17 at 1.00.01 pm

Screen shot 2016 01 17 at 1.00.12 pm

Screen shot 2016 01 17 at 1.00.06 pm

Explanation

In the reaction below, a ketone is protonated by a strong acid. This triggers the deprotonation of the weakly acidic hydrogen bonded to the alpha carbon by a bromide ion and formation of an alkene functional group.

Screen shot 2016 01 17 at 1.00.53 pm

9

What is the IUPAC name of the following compound?

Untitled

3-bromo-2-methylcyclohexene

None of the other answers

1-bromo-2-methyl-2-cycloxene

6-bromo-1-methylcyclohexene

2-bromo-1-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.

10

What is the product of the following reaction?

Image13

and

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).

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