Question 1

What is the correct IUPAC name for the compound shown in the first image?

Accepted Answer

3,3-dimethyl-1-butanamine

Question 2

Between aniline and cyclohexylamine (second image), which is the stronger base and why?

Accepted Answer

Cyclohexylamine, because the lone pair on nitrogen is not delocalized and is more available for protonation.

Question 3

Which compound in the third image is the stronger base and why?

Accepted Answer

Pyrrolidine, because protonation does not disrupt aromaticity.

Question 4

What is the major organic product of the reaction shown in the fourth image (benzaldehyde + methylamine, acid catalyst)?

Accepted Answer

N-methylbenzaldimine (Schiff base)

Question 5

What is the structure of the product formed in the reaction shown in the sixth and seventh images (piperidine + excess methyl iodide)?

Accepted Answer

N,N-dimethylpiperidinium iodide

Question 6

What is the product of the reaction between benzoyl chloride and isobutylamine as shown in the eighth and ninth images?

Accepted Answer

N-isobutylbenzamide

Question 7

What is the product of the reaction sequence shown in the tenth and eleventh images (1. NaNO$$_2$$, HCl; 2. CuBr) on 1-amino-1,2,3,4-tetrahydronaphthalene?

Accepted Answer

1-bromo-1,2,3,4-tetrahydronaphthalene

Question 8

What is the product of the reaction sequence shown in the twelfth and thirteenth images (1. NaNO$$_2$$, HCl; 2. CuCN) on 2-methylaniline?

Accepted Answer

2-methylbenzonitrile

Question 9

What is the product of the reaction sequence shown in the fourteenth and fifteenth images (1. NaNO$$_2$$, HCl; 2. CuCN) on 4-aminoacetophenone?

Accepted Answer

4-cyanoacetophenone

Question 10

Which of the following best describes the mechanism for the transformation of an aromatic amine to an aryl bromide using NaNO$$_2/$$HCl followed by CuBr?

Accepted Answer

Sandmeyer reaction via diazonium salt intermediate

Question 11

Which of the following amines can be resolved into enantiomers?

Accepted Answer

2-pentanamine

Question 12

Arrange the following compounds in order of increasing boiling point: ethyl methyl ether, N-methylethanamine, 1-propanamine, 1-propanol.

Accepted Answer

Ethyl methyl ether \u003c N-methylethanamine \u003c 1-propanamine \u003c 1-propanol

Question 13

Which of the following is a tertiary amine?

Accepted Answer

N,N-dimethylaniline

Question 14

What reagents would you use to convert a ketone to a primary amine via the oxime intermediate?

Accepted Answer

1) NH$$_2OH$$, 2) H$$_2/Ni$$

Question 15

Which of the following best explains why aniline is a weaker base than cyclohexylamine?

Accepted Answer

The lone pair on aniline's nitrogen is delocalized into the aromatic ring, reducing its availability for protonation.

Organic Chemistry Amines and Reactions Study Guide

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