Question 1

Provide the IUPAC name of (CH3)3CCH2CH2NHCH2CH3.

Accepted Answer

N-ethyl-3,

Question 2

How might one distinguish a sample of trimethylamine from a sample of n-propylamine using IR spectroscopy?

Accepted Answer

n-Propylamine would

Question 3

Why can't N-methyl-2-propanamine be resolved into isolable enantiomers even though the compound is chiral?

Accepted Answer

Enantiomers intercon

Question 4

Provide the correct IUPAC name for the following amine.

Accepted Answer

A)  4-(methylamino)-2-methyl-1-pentene 
B)  2,N-dimethyl-1-penten-4-amine 
C)  4,N-dimethyl-4-penten-2-amine 
D)  1,3,N-trimethyl-3-buten-1-amine 
A)  4-(methylamino)-2-methyl-1-pentene 
B)  2,N-dimethyl-1-penten-4-amine 
C)  4,N-dimethyl-4-penten-2-amine 
D)  1,3,N-trimethyl-3-buten-1-amine

Question 5

When pyridine is treated with a mixture of nitric and sulfuric acids, the major product is:

Accepted Answer

A)  2-nitropyridine. 
B)  3-nitropyridine. 
C)  4-nitropyridine. 
D)  3-aminopyridine. 
E)  4-aminopyridine. 
A)  2-nitropyridine. 
B)  3-nitropyridine. 
C)  4-nitropyridine. 
D)  3-aminopyridine. 
E)  4-aminopyridine.

Question 6

Provide the name for the compound below.

Accepted Answer

The answer of Provide the name for the compound below....

Question 7

Circle all of the following structures that can be resolved into pure enantiomers.

Accepted Answer

The answer of Circle all of the following structures that...

Question 8

What compound results from the reaction below?

Accepted Answer

A)  imine 
B)  amide 
C)  primary amine 
D)  quaternary ammonium salt 
E)  nitrous acid 
A)  imine 
B)  amide 
C)  primary amine 
D)  quaternary ammonium salt 
E)  nitrous acid

Question 9

The following structure has been used in monitoring the development of amyloid plaques in Alzheimer's patients (J. Med. Chem. 2011, 949). Which sequence correctly ranks the following nitrogens in order of increasing pKb value?

Accepted Answer

A)  2 < 3 < 1 
B)  3 < 2 < 1 
C)  2 < 1 < 3 
D)  1 < 3 < 2 
A)  2 < 3 < 1 
B)  3 < 2 < 1 
C)  2 < 1 < 3 
D)  1 < 3 < 2

Question 10

Provide the structure of N-ethyl-1-butanamine.

Accepted Answer

The answer of Provide the structure of N-ethyl-1-butanamine....

Question 11

The product of the reaction below has been found to be a potent anticancer agent (J.
Med. Chem. 2010, 6867). Predict the structure of the product of the following reaction.

Accepted Answer

The answer of The product of the reaction below has...

Question 12

Devise an efficient method for preparing 2-phenylethanamine from 2-phenylethanol.

Accepted Answer

1. PCC 2. H₂NOH 3. H₂,

Question 13

What reagent is needed to accomplish the transformation below?

Accepted Answer

The answer of What reagent is needed to accomplish the...

Question 14

Which compound would react most rapidly with sodium methoxide and heat?

Accepted Answer

A)  chlorobenzene 
B)  2-chloropyridine 
C)  3-chloropyridine 
D)  3-chloropyrrole 
A)  chlorobenzene 
B)  2-chloropyridine 
C)  3-chloropyridine 
D)  3-chloropyrrole

Question 15

Which of the following is a secondary amine?

Accepted Answer

A)  cyclohexylamine 
B)  3-pentanamine 
C)  methylamine 
D)  N,N-dimethylaniline 
E)  N-ethyl-1-propanamine 
A)  cyclohexylamine 
B)  3-pentanamine 
C)  methylamine 
D)  N,N-dimethylaniline 
E)  N-ethyl-1-propanamine

Question 16

Provide the major organic product of the following reaction.

Accepted Answer

The answer of Provide the major organic product of the...

Question 17

The nitrogen atom of trimethylamine is ________ hybridized which is reflected in the CNC bond angle of ________.

Accepted Answer

A)  sp, 180° 
B)  sp2, 120° 
C)  sp2, 108° 
D)  sp3, 120° 
E)  sp3, 108° 
A)  sp, 180° 
B)  sp2, 120° 
C)  sp2, 108° 
D)  sp3, 120° 
E)  sp3, 108°

Question 18

Circle the stronger base in the pair below, and briefly explain your choice.

Accepted Answer

Pyrrolidine is the s

Question 19

Arrange the following compounds in order of increasing boiling point:
CH3NHCH2CH3, CH3OCH2CH3, (CH3)3N, and CH3CH2CH2OH.

Accepted Answer

(CH₃)₃N < CH

Question 20

When pyrrole undergoes electrophilic aromatic substitution, at which position does substitution occur?

Accepted Answer

A)  2-position 
B)  3-position 
C)  4-position 
A)  2-position 
B)  3-position 
C)  4-position

Exam 19: Amines

Provide the IUPAC name of (CH3)3CCH2CH2NHCH2CH3.

How might one distinguish a sample of trimethylamine from a sample of n-propylamine using IR spectroscopy?

Why can't N-methyl-2-propanamine be resolved into isolable enantiomers even though the compound is chiral?

Provide the correct IUPAC name for the following amine.

When pyridine is treated with a mixture of nitric and sulfuric acids, the major product is:

Provide the name for the compound below.

Circle all of the following structures that can be resolved into pure enantiomers.

What compound results from the reaction below?

The following structure has been used in monitoring the development of amyloid plaques in Alzheimer's patients (J. Med. Chem. 2011, 949). Which sequence correctly ranks the following nitrogens in order of increasing pKb value?

Provide the structure of N-ethyl-1-butanamine.

The product of the reaction below has been found to be a potent anticancer agent (J. Med. Chem. 2010, 6867). Predict the structure of the product of the following reaction.

Devise an efficient method for preparing 2-phenylethanamine from 2-phenylethanol.

What reagent is needed to accomplish the transformation below?

Which compound would react most rapidly with sodium methoxide and heat?

Which of the following is a secondary amine?

Provide the major organic product of the following reaction.

The nitrogen atom of trimethylamine is ________ hybridized which is reflected in the CNC bond angle of ________.

Circle the stronger base in the pair below, and briefly explain your choice.

Arrange the following compounds in order of increasing boiling point: CH3NHCH2CH3, CH3OCH2CH3, (CH3)3N, and CH3CH2CH2OH.

When pyrrole undergoes electrophilic aromatic substitution, at which position does substitution occur?

Introduction and Review

Structure and Properties of Organic Molecules

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides: Nucleophilic Substitution and Elimination

Structure and Synthesis of Alkenes

Reactions of Alkenes

Alkynes

Structure and Synthesis of Alcohols

Reactions of Alcohols

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Ethers, Epoxides, and Thioethers

Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Aromatic Compounds

Reactions of Aromatic Compounds

Ketones and Aldehydes

Carboxylic Acids

Carboxylic Acid Derivatives

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Provide the IUPAC name of (CH₃)₃CCH₂CH₂NHCH₂CH₃.

The following structure has been used in monitoring the development of amyloid plaques in Alzheimer's patients (J. Med. Chem. 2011, 949). Which sequence correctly ranks the following nitrogens in order of increasing pK_b value?

The nitrogen atom of trimethylamine is hybridized which is reflected in the CNC bond angle of .

Arrange the following compounds in order of increasing boiling point: CH₃NHCH₂CH₃, CH₃OCH₂CH₃, (CH₃)₃N, and CH₃CH₂CH₂OH.