Deck 15: Carboxylic Acids and Nitriles

Question 1

Instructions: Give the major organic product(s)for each of the following reactions or sequences of reactions.Show all relevant stereochemistry.

Give major product(s):

Answer 1

Question 2

Instructions: Give the major organic product(s)for each of the following reactions or sequences of reactions.Show all relevant stereochemistry.

Refer to instructions and answer the following questions.
a) Give major product(s):

b) Draw the stucture of the intermediate procuct(s) that form(s).

Answer 2

a)
b)

Question 3

Instructions: Consider the data below to answer the following question(s).
When CO₂ is bubbled through an ether solution of benzylmagnesium bromide and the resulting mixture is acidified,phenylacetic acid is produced.Any unreacted benzylmagnesium bromide is converted to toluene in the acidification step.

Refer to instructions.This reaction can be described as a _____ process.

A)carbonylation
B)carboxylation
C)carbaniolation
D)cationation

Answer 3

carboxylation

Question 4

What is the order of increasing acidity for the following compounds? (least to most)

A)IV,I,III,II
B)IV,II,III,I
C)II,III,I,IV
D)I,III,II,IV

Question 5

Instructions: Give the major organic product(s)for each of the following reactions or sequences of reactions.Show all relevant stereochemistry.
Give major product(s):

Question 6

Which of the following would represent the correct reaction conditions for the following conversion?

A)1)KMnO₄,2)LiAlH₄
B)1)Mg,ether,2)CO₂,3)LiAlH₄
C)1)NaOH,H₂O,2)LiAlH₄
D)1)SOCl₂,benzene,2)LiAlH₄
E)either b or c

Question 7

Instructions: Give the major organic product(s)for each of the following reactions or sequences of reactions.Show all relevant stereochemistry.

Give major product(s):

Question 8

Which of the following has the highest boiling point?

A)butanoic acid
B)butan-2-ol
C)hexanoic acid
D)heptan-3-one

Question 9

Complete the following reaction sequence with the missing major organic products.

Question 10

Instructions: Carboxylic acids are synthesized from alkyl halides via Grignard reagent carboxylation or nitrile hydrolysis.Choose the best method for affecting each of the following conversions.Explain each of your choices.If neither method is appropriate,explain.
Choose best method:

Question 11

The product shown can be synthesized by two different pathways as shown by the reaction conditions.Draw the structure of starting materials that should be placed in each of the boxes.

Question 12

What is the major organic product obtained from the following reaction?

A)
B)
C)
D)

Question 13

What is the IUPAC name of the following compound?

A)5,5-dimethyl-5-phenylpentanoic acid
B)5-methyl-5-phenylhexanoic acid
C)2,2-dimethylphenylpropanoic acid
D)5,5-dimethyl-5-phenylbutanal

Question 14

Which of the following is the correct order of decreasing acid strength (more acidic > less acidic)?

A)FCH₂COOH > CH₃COOH > F₂CHCOOH
B)FCH₂COOH > CH₃COOH > CH₃OH
C)CH₃CH₂OH > ClCH₂COOH > BrCH₂COOH
D)CH₃COOH > ClCH₂COOH > CH₃OH

Question 15

Which of the following does not represent a similarity between nitriles and carboxylic acids?

A)contain 3 carbon bonds to an electronegative element
B)contain two p bonds.
C)act as electrophiles
D)undergo nucleophilic substitution reactions
E)all of these are characteristic of both nitriles and carboxylic acids.

Question 16

What is the order of increasing reactivity for the following compounds in electrophillic aromatic substitution reactions? (least to most reactive)

A)IV,I,II,III
B)III,II,I,IV
C)II,III,I,IV

Question 17

Instructions: Give the major organic product(s)for each of the following reactions or sequences of reactions.Show all relevant stereochemistry.

Give major product(s):

Question 18

Instructions: Carboxylic acids are synthesized from alkyl halides via Grignard reagent carboxylation or nitrile hydrolysis.Choose the best method for affecting each of the following conversions.Explain each of your choices.If neither method is appropriate,explain.
Choose best method:

Question 19

What is the major organic product obtained from the following reaction?

A)
B)
C)
D)

Question 20

Draw the structure of (Z)-4-methylhex-3-enoic acid.

Question 21

What is the major organic product obtained from the following reaction?

A)
B)
C)
D)

Question 22

Based on the following IR spectrum,this compound would be classified as:
Spectrum obtained from: SDBSWeb : http://riodb01.ibase.aist.go.jp/sdbs/ (National Institute of Advanced Industrial Science and Technology,11-07-08)

A)aliphatic carboxylic acid
B)aromatic carboxylic acid
C)aliphatic nitrile
D)aromatic nitrile
E)carbonyl containing an alcohol functional group

Question 23

Instructions: Consider the following ¹H NMR to answer the following question.
Spectrum obtained from: SDBSWeb : http://riodb01.ibase.aist.go.jp/sdbs/ (National Institute of Advanced Industrial Science and Technology,11-07-08)

Refer to instructions.This compound is known to contain both a -C=O group and an -OH group.Based on this spectrum,this compound would be classified as:

A)aromatic carboxylic acid
B)aliphatic carboxylic acid
C)carbonyl containing an alcohol functional group
D)either a or b