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Exam 20: Carboxylic Acids

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Question 21

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List the following weak acids in order of increasing acidity (from lowest to highest.) .

A) 4 < 3 < 2 < 1 < 5
B) 4 < 1 < 3 < 2 < 5
C) 5 < 2 < 3 < 1 < 4
D) 4 < 1 < 2 < 5 < 3
E) 1 < 2 < 4 < 3 < 5

F) A) and B)
G) A) and C)

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Question 22

Multiple Choice

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An unknown compound is insoluble in water but dissolves in an aqueous solution of sodium bicarbonate with a release of carbon dioxide bubbles. The compound is almost certainly ________.

A) a carboxylic acid
B) an amine
C) an aldehyde
D) an alkyl chloride
E) an alcohol

F) B) and E)
G) A) and E)

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Question 23

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Provide the major organic product for the following reaction.

Provide the major organic product for the following reaction.

The methyl ester of a carboxylic acid can be synthesized directly using ________.

How can one prepare ethyl cyclohexyl ketone from cyclohexanecarboxylic acid?

Lithium aluminum hydride reduces carboxylic acids to primary alcohols via what intermediate?

Starting with any alkene, how could you make pimelic acid (HOOC(CH₂)₅COOH)?

An ether solution of PhCO₂H (A) , PhNH₂ (B) , and PhCH₃ (C) is extracted with aqueous NaOH. The ether layer will contain what compound(s) after the extraction?

Which of the following compounds is the strongest acid?

Which of the following reagents can be used to convert a carboxylic acid directly into its corresponding acid chloride derivative?

Provide the major organic product of the following reaction.

Provide a detailed, stepwise mechanism for the methylation of a carboxylic acid with diazomethane.

Provide the structure of trans-1,3-cyclohexanedicarboxylic acid.

Provide the major organic product of the reaction shown below.

Esters and amides are most easily made by nucleophilic acyl substitution reactions on ________.

Which of the following is the strongest acid?

Provide a mechanism for the reaction shown below.

Provide the major organic product of the reaction shown below.

Provide the structure of pent-3-ynoic acid.