Question 1

Which of the following would best represent the form of ethylamine (pKa) at physiological pH?

Accepted Answer

A) CH3CH2NH3+ 
B) CH3CH2NH2 
C) CH3CH2NH- 
D) a combination of a and b 
A) CH3CH2NH3+ 
B) CH3CH2NH2 
C) CH3CH2NH- 
D) a combination of a and b A

Question 2

Exhibit 24-4
Refer to the reaction below to answer the following question(s):  
-Refer to Exhibit 24-4.Draw arrows on the structures provided below which show electron flow in the complete stepwise mechanism for the reaction above.

Accepted Answer

The answer of Exhibit 24-4
Refer to the reaction below to...

Question 3

Name:
​

Accepted Answer

N-isopropyl-N-methylcyclobutylamine

Question 4

The amino acid phenylalanine has the structure below.   Which of the following is the best representation of this acid at pH 7.3?

Accepted Answer

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

Question 5

Which of the following is not classified as a heterocycle?

Accepted Answer

A)    
B)    
C)    
D)    
E) c and d 
A)    
B)    
C)    
D)    
E) c and d

Question 6

Draw the product of the reaction of the following substance with 1) LiAlH4 in ether,2) H2O.From what alkyl bromide could this substance be produced when reacted with NaCN? Atoms other than carbon and hydrogen are labeled.

Accepted Answer

Question 7

Exhibit 24-8
Refer to the data below to answer the following question(s):
Triclocarban is a disinfectant prepared from 3,4-dichloroaniline and 4-chlorophenylisocyanate.  
-Refer to Exhibit 24-8.Propose a mechanism for the reaction of 3,4-dichloroaniline and 4-chlorophenylisocyanate to yield Triclocarban.

Accepted Answer

The answer of Exhibit 24-8
Refer to the data below to...

Question 8

Exhibit 24-8
Refer to the data below to answer the following question(s):
Triclocarban is a disinfectant prepared from 3,4-dichloroaniline and 4-chlorophenylisocyanate.  
-Refer to Exhibit 24-8.Prepare 4-chlorophenylisocyanate from toluene.

Accepted Answer

The answer of Exhibit 24-8
Refer to the data below to...

Question 9

Rank the following compounds in order of increasing basicity.Label the least basic compound "1" and the most basic compound "4".Place the number corresponding to the compound's rank in the blank below the compound.

Accepted Answer

The answer of Rank the following compounds in order of...

Question 10

Which of the following methods of preparation of amines can be used to prepare primary,secondary,and tertiary amines?

Accepted Answer

A) reduction of a nitrile 
B) Gabriel synthesis from an alkyl halide 
C) reduction amination of a ketone 
D) Hofman rearrangement of an amide 
E) None of these methods is applicable to all types of amines. 
A) reduction of a nitrile 
B) Gabriel synthesis from an alkyl halide 
C) reduction amination of a ketone 
D) Hofman rearrangement of an amide 
E) None of these methods is applicable to all types of amines.

Question 11

An unknown substance produced the following spectrum.   This unknown is likely to be a:

Accepted Answer

A) primary amine 
B) secondary amine 
C) tertiary amine 
D) amide 
A) primary amine 
B) secondary amine 
C) tertiary amine 
D) amide

Question 12

​Draw the mechanism for the Hofmann rearrangement of acetamide to acetamine.

Accepted Answer

The answer of ​Draw the mechanism for the Hofmann rearrangement...

Question 13

​Draw the mechanism of the Sandmeyer reaction that converts o-methyl aniline to o-bromotoluene.

Accepted Answer

The answer of ​Draw the mechanism of the Sandmeyer reaction...

Question 14

Compared to pentylamine,pentane is

Accepted Answer

A) more soluble in water. 
B) has a higher boiling point. 
C) is less basic. 
D) more offensive in terms of odor. 
A) more soluble in water. 
B) has a higher boiling point. 
C) is less basic. 
D) more offensive in terms of odor.

Question 15

Propose a structure that is consistent with the following spectral data:
MS:
M+ at 73
IR:
3350 cm−1 (weak,single band)
1H NMR:
δ1.05 (br s,1H),δ1.15 (t,6H),δ2.65 (q,4H)

Accepted Answer

diethylami

Question 16

Exhibit 24-3
Refer to the Table of pKS1U1B1aS1U1B0s below to answer the following question(s):
pKS1U1B1aS1U1B0s of Some Arylammonium Ions   
 
-Refer to Exhibit 24-3.Explain the difference in acidity between p-cyanoanilinium ion and anilinium ion.Use both words and structures.

Accepted Answer

p-Cyanoanilinium ion is a stronger acid

Question 17

Which of the following is not a valid comparison of the spectral data for alkyl amines and alkyl alcohols?

Accepted Answer

A) IR: strong absorptions > 3000 cm-1. 
B) MS: peaks due α-cleavage 
C) (13C NMR: adjacent carbon signal shifted downfield relative to an alkane) 
D) (1H NMR: proton bonded to the heteroatom appears over a wide range) 
E) All are valid comparisons between the spectral data of amines and alcohols. 
A) IR: strong absorptions > 3000 cm-1. 
B) MS: peaks due α-cleavage 
C) (13C NMR: adjacent carbon signal shifted downfield relative to an alkane) 
D) (1H NMR: proton bonded to the heteroatom appears over a wide range) 
E) All are valid comparisons between the spectral data of amines and alcohols.

Question 18

Write the equation for the reaction represented by the pKa of methyl amine.

Accepted Answer

Question 19

Name:

Accepted Answer

methyl 2-a

Question 20

What is the percentage of neutral species in a 0.00500 M solution of pyridine at pH 9.50? pKa of pyridine is 5.25.

Accepted Answer

A) 25% 
B) 75% 
C) 50% 
D) nearly 100% 
E) close to 0% 
A) 25% 
B) 75% 
C) 50% 
D) nearly 100% 
E) close to 0%

Exam 24: Amines and Heterocycles

Which of the following would best represent the form of ethylamine (pKa) at physiological pH?

Exhibit 24-4 Refer to the reaction below to answer the following question(s): -Refer to Exhibit 24-4.Draw arrows on the structures provided below which show electron flow in the complete stepwise mechanism for the reaction above.

Name: ​

The amino acid phenylalanine has the structure below. Which of the following is the best representation of this acid at pH 7.3?

Which of the following is not classified as a heterocycle?

Draw the product of the reaction of the following substance with 1) LiAlH4 in ether,2) H2O.From what alkyl bromide could this substance be produced when reacted with NaCN? Atoms other than carbon and hydrogen are labeled.

Exhibit 24-8 Refer to the data below to answer the following question(s): Triclocarban is a disinfectant prepared from 3,4-dichloroaniline and 4-chlorophenylisocyanate. -Refer to Exhibit 24-8.Prepare 4-chlorophenylisocyanate from toluene.

Rank the following compounds in order of increasing basicity.Label the least basic compound "1" and the most basic compound "4".Place the number corresponding to the compound's rank in the blank below the compound.

Which of the following methods of preparation of amines can be used to prepare primary,secondary,and tertiary amines?

An unknown substance produced the following spectrum. This unknown is likely to be a:

​Draw the mechanism for the Hofmann rearrangement of acetamide to acetamine.

​Draw the mechanism of the Sandmeyer reaction that converts o-methyl aniline to o-bromotoluene.

Compared to pentylamine,pentane is

Propose a structure that is consistent with the following spectral data: MS: M+ at 73 IR: 3350 cm−1 (weak,single band) 1H NMR: δ1.05 (br s,1H),δ1.15 (t,6H),δ2.65 (q,4H)

Exhibit 24-3 Refer to the Table of pKas below to answer the following question(s): pKas of Some Arylammonium Ions -Refer to Exhibit 24-3.Explain the difference in acidity between p-cyanoanilinium ion and anilinium ion.Use both words and structures.

Which of the following is not a valid comparison of the spectral data for alkyl amines and alkyl alcohols?

Write the equation for the reaction represented by the pKa of methyl amine.

Name:

What is the percentage of neutral species in a 0.00500 M solution of pyridine at pH 9.50? pKa of pyridine is 5.25.

Structure and Bonding

Polar Covalent Bonds;acids and Bases

Organic Compounds: Alkanes and Their Stereochemistry

Organic Compounds: Cycloalkanes and Their Stereochemistry

Stereochemistry at Tetrahedral Centers

An Overview of Organic Reactions

Par 1

Alkenes: Structure and Reactivity

Alkenes: Reactions and Synthesis

Alkynes: an Introduction to Organic Synthesis

Organohalides

Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations

Par 2

Structure Determination: Mass Spectrometry and Infrared Spectroscopy

Structure Determination: Nuclear Magnetic Resonance Spectroscopy

Conjugated Compounds and Ultraviolet Spectroscopy

Par 3

Benzene and Aromaticity

Chemistry of Benzene: Electrophilic Aromatic Substitution

Alcohols and Phenols

Ethers and Epoxides;thiols and Sulfides

Aldehydes and Ketones: Nucleophilic Addition Reactions

Par 4

Carboxylic Acids and Nitriles

Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

Carbonyl Alpha-Substitution Reactions

Carbonyl Condensation Reactions

Par 5

Biomolecules: Carbohydrates

Biomolecules: Amino Acids,peptides,and Proteins

Par 7

Biomolecules: Lipids

Biomolecules: Nucleic Acids

The Organic Chemistry of Metabolic Pathways

Orbitals and Organic Chemistry: Pericyclic Reactions

Synthetic Polymers

Par 1

Filters

Which of the following would best represent the form of ethylamine (pK_a) at physiological pH?

Name:

Draw the product of the reaction of the following substance with 1) LiAlH₄ in ether,2) H₂O.From what alkyl bromide could this substance be produced when reacted with NaCN? Atoms other than carbon and hydrogen are labeled.

Draw the mechanism for the Hofmann rearrangement of acetamide to acetamine.

Draw the mechanism of the Sandmeyer reaction that converts o-methyl aniline to o-bromotoluene.

Propose a structure that is consistent with the following spectral data: MS: M⁺ at 73 IR: 3350 cm−¹ (weak,single band) ¹H NMR: δ1.05 (br s,1H),δ1.15 (t,6H),δ2.65 (q,4H)

Exhibit 24-3 Refer to the Table of pK_as below to answer the following question(s): pK_as of Some Arylammonium Ions -Refer to Exhibit 24-3.Explain the difference in acidity between p-cyanoanilinium ion and anilinium ion.Use both words and structures.

Write the equation for the reaction represented by the pK_a of methyl amine.

What is the percentage of neutral species in a 0.00500 M solution of pyridine at pH 9.50? pK_a of pyridine is 5.25.