Deck 23: The Chemistry of Amines

Question 1

Name the amine CH₃CH₂NHCH₂CH₃ using its common and IUPAC name, then classify the amine as primary, secondary, or tertiary.

Answer 1

The amine has the common name diethylamine. The IUPAC name is N-ethylethanamine. It is a secondary amine.

Question 2

Name the amine using its common and IUPAC name, then classify the amine as primary, secondary, or tertiary.

Answer 2

The common name is N,N-dimethylpropylamine. The IUPAC name is N,N-dimethylpropan-1-amine. The amine is a tertiary amine.

Question 3

Draw the structure of 3,5-diethylaniline, then classify the amine as primary, secondary, or tertiary.

Answer 3

An aniline is a benzene ring with a primary amine substituent. Add the ethyl groups to carbons 3 and 5.

Question 4

An amine is considered a principal group for nomenclature in multifunctional compounds. How does it compare with the other principal groups?

A) The amine has higher priority than a carboxylic acid.
B) The amine has higher priority than an aldehyde.
C) The amine has higher priority than an alcohol.
D) None of the other choices.

Question 5

Can this amine be resolved into enantiomers at room temperature? Explain why or why not.

Question 6

Identify the compound with the highest boiling point.

A) CH₃CH₂CH₂CH₂NH₂
B) CH₃CH₂CH₂CH₂OH
C) CH₃CH₂CH₂CH₂CH₃
D) CH₃CH₂OCH₂CH₃

Question 7

Draw a structure with the molecular formula C₅H₉N, which is a chiral primary amine with no triple bonds. (There is more than one correct answer.)

Question 8

Propose a structure for a compound with the molecular formula C₅H₁₁N that has the NMR spectra:
¹H NMR $\delta$ 1.28 (s, 6H), 1.58 (s, 2H), 4.91 (dd, 1H), 5.20 (dd, 1H), 5.54 (dd, 1H) ppm
¹³C NMR $\delta$ 32.7, 52.7, 111.2, 145.4

Question 9

A student has produced the two isomers, A and B, and wants to use infrared (IR), ¹H, and ¹³C NMR to distinguish between them. Identify what features in each spectroscopy method the student can quickly use to conclusively identify which isomer is which.

Question 10

Rank the amines from most basic to least basic.

A) A > B > C
B) C > B > A
C) C > A > B
D) B > A > C

Question 11

A student is hydrolyzing the amide below, and the reaction did not go to completion. The student wants to isolate just the neutral amine product. Design a separation and isolation method based on the basicities of all three compounds.

Question 12

Give the structure of the nucleophile that would react with CH₃I to give triethylmethylphosphonium iodide. Show any unshared electron pairs and charges, where applicable.

Question 13

Provide the major organic product for the reaction. If you believe no product will be formed, explain why.

Question 14

Deduce the structure of the starting material for the reaction.

Question 15

Determine the starting materials that could be used in two synthetic routes to make the amine by reductive amination.

Question 16

Predict the major organic product for the reaction. If you believe no reaction will occur, write NR and explain why.

Question 17

An unknown compound with the molecular formula C₁₅H₂₃N is treated with excess CH₃I and heat, followed by Ag₂O to give these two products. Deduce the structure of the unknown compound.

Question 18

Outline a synthesis for the preparation of 4-aminobenzenesulfonate from aniline.

Question 19

Outline a synthesis of 1,3,5-trimethylbenzene from 2,4,6-trimethylaniline.

Question 20

Identify the reagents needed for this synthetic sequence.

Question 21

Aryldiazonium salts cannot be directly converted to

A) Ph-X, where X is a halide.
B) Ph-CN.
C) Ph-OH.
D) Ph-CH₃.

Question 22

Deduce the structures of the aniline and phenol that are used to produce this azo dye.

Question 23

Predict the major organic product for the two reactions. If no reaction occurs, write NR and explain why.
​a.
​
b.

Question 24

A student wants to make this amine using either the Gabriel synthesis or the Staudinger reaction. Will either method work? If so, deduce the structures of the starting materials. If not, explain why.

Question 25

Cyclohexanecarbonyl chloride is converted to cyclohexanamine by this reaction. The major product formed in step 1 is an isocyanate. Draw the isocyanate and a curved-arrow mechanism showing how it is formed.