Question 1

Provide the major organic product of the following reaction.

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Question 2

What products result from the reaction of sodium propanoate with hydrobromic acid?

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Question 3

Show how you could convert benzene to benzoic acid.

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Question 4

Hept-3-yne yields what acids upon treatment with concentrated permanganate of ozone followed by water?

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Question 5

The combination of a carbonyl group and a hydroxyl group on the same carbon atom is called a ________ group.

Accepted Answer

A)  carbamate 
B)  carbonate 
C)  urethane 
D)  carboxyl 
E)  carboxylate

Question 6

Give a detailed, stepwise mechanism for the Fischer esterification of acetic acid with methanol.

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Question 7

Provide the major organic product of the reaction shown below.

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Question 8

The pKa₁ for oxalic acid (pKa = 1.27) is much lower than the pKa₁ of glutaric acid (pKa = 4.35). Briefly explain why.

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Question 9

After completing the synthesis of 3-methylpentanoic acid, which of the following treatments will neutralize the mineral acids and facilitate the distribution of the organic acid from the organic layer to the aqueous extraction layer?

Accepted Answer

A)  extraction with aqueous NaCl 
B)  extraction with ether 
C)  extraction with aqueous NaHCO3 
D)  extraction with water 
E)  extraction with dilute aqueous HCl

Question 10

Which of the following reactions involves the formation of a methyl ester from a carboxylic acid?

Accepted Answer

A)  Cope elimination 
B)  Hell-Volhard-Zelinsky reaction 
C)  reaction with CH2N2 
D)  Hunsdiecker reaction 
E)  hydroboration with diborane

Question 11

An unknown alkyne was subjected to concentrated KMnO₄ and only one product was isolated. The spectral information for 1H NMR of the product is given below. δ (ppm) = 11.0 (1H, broad s), 2.39 (2H, q), 1.16 (3H, t) What is the structure of the starting alkyne?

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Question 12

What are the products of the reaction of benzoic acid with thionyl chloride?

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Question 13

Provide the sequence of reagents needed to accomplish the conversion below.

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Question 14

Provide the structure of glutaric acid.

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Question 15

Suggest a sequence of synthetic steps through which phenylacetic acid can be prepared from toluene via phenylacetonitrile.

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Question 16

Provide a detailed, stepwise mechanism for the reaction of acetyl chloride with methanol to produce methyl acetate and HCl.

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Question 17

What is the best way to perform the transformation shown below?

Accepted Answer

A)  1. NaCN 2. H3O+ 
B)  1.Mg 2. CO 3. H3O+ 
C)  concentrated KMnO4 
D)  Both A and B would work

Question 18

Provide the IUPAC name for the compound shown below.

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Question 19

Provide the major organic product of the following reaction.

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Question 20

Provide the major organic product of the following reaction.

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Exam 20: Carboxylic Acids

Provide the major organic product of the following reaction.

What products result from the reaction of sodium propanoate with hydrobromic acid?

Show how you could convert benzene to benzoic acid.

Hept-3-yne yields what acids upon treatment with concentrated permanganate of ozone followed by water?

The combination of a carbonyl group and a hydroxyl group on the same carbon atom is called a ________ group.

Give a detailed, stepwise mechanism for the Fischer esterification of acetic acid with methanol.

Provide the major organic product of the reaction shown below.

The pKa1 for oxalic acid (pKa = 1.27) is much lower than the pKa1 of glutaric acid (pKa = 4.35). Briefly explain why.

After completing the synthesis of 3-methylpentanoic acid, which of the following treatments will neutralize the mineral acids and facilitate the distribution of the organic acid from the organic layer to the aqueous extraction layer?

Which of the following reactions involves the formation of a methyl ester from a carboxylic acid?

An unknown alkyne was subjected to concentrated KMnO4 and only one product was isolated. The spectral information for 1H NMR of the product is given below. δ (ppm) = 11.0 (1H, broad s), 2.39 (2H, q), 1.16 (3H, t) What is the structure of the starting alkyne?

What are the products of the reaction of benzoic acid with thionyl chloride?

Provide the sequence of reagents needed to accomplish the conversion below.

Provide the structure of glutaric acid.

Suggest a sequence of synthetic steps through which phenylacetic acid can be prepared from toluene via phenylacetonitrile.

Provide a detailed, stepwise mechanism for the reaction of acetyl chloride with methanol to produce methyl acetate and HCl.

What is the best way to perform the transformation shown below?

Provide the IUPAC name for the compound shown below.

Provide the major organic product of the following reaction.

Provide the major organic product of the following reaction.

The pKa₁ for oxalic acid (pKa = 1.27) is much lower than the pKa₁ of glutaric acid (pKa = 4.35). Briefly explain why.

An unknown alkyne was subjected to concentrated KMnO₄ and only one product was isolated. The spectral information for 1H NMR of the product is given below. δ (ppm) = 11.0 (1H, broad s), 2.39 (2H, q), 1.16 (3H, t) What is the structure of the starting alkyne?