Question 1

Arrange the following amines in order of decreasing basicity (most to least)in aqueous solution: NH3
CH3CH2CH2NH2
(CH3CH2CH2)2NH
(CH3CH2CH2)3N
I
II
III
IV

Accepted Answer

A)  IV > III > II > I 
B)  III > II > IV > I 
C)  I > IV > II > III 
D)  II > III > I > IV 
E)  III > I > II > IV 
A)  IV > III > II > I 
B)  III > II > IV > I 
C)  I > IV > II > III 
D)  II > III > I > IV 
E)  III > I > II > IV

Question 2

Arrange the following amines in order of increasing basicity (least to most)in aqueous solution: NH3
CH3CH2CH2NH2
(CH3CH2CH2)2NH
(CH3CH2CH2)3N
I
II
III
IV

Accepted Answer

A)  IV < III < II < I 
B)  III < II < IV < I 
C)  I < IV < II < III 
D)  II < III < I < IV 
E)  III < I < II < IV 
A)  IV < III < II < I 
B)  III < II < IV < I 
C)  I < IV < II < III 
D)  II < III < I < IV 
E)  III < I < II < IV

Question 3

Which of the following bases has a conjugate acid with the smallest pKa?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 4

Arylamines are less basic than alkylamines because of _______________.

Accepted Answer

delocalization of th

Question 5

What is the final product of the reaction sequence:

Accepted Answer

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

Question 6

Which combination of reactants will not produce   ?

Accepted Answer

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

Question 7

Which is not an intermediate in the Hofmann degradation reaction?

Accepted Answer

A)  RN=C=O 
B) 
  
C) 
  
D) 
  
E) 
  
A)  RN=C=O 
B) 
  
C) 
  
D) 
  
E)

Question 8

What compound is likely to be obtained via the following reaction sequence?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 9

Arrange the following amines in order of decreasing basicity (most to least)in the gas phase: NH3
CH3CH2CH2NH2
(CH3CH2CH2)2NH
(CH3CH2CH2)3N
I
II
III
IV

Accepted Answer

A)  IV > III > II > I 
B)  III > II > IV > I 
C)  I > IV > II > III 
D)  II > III > I > IV 
E)  III > I > II > IV 
A)  IV > III > II > I 
B)  III > II > IV > I 
C)  I > IV > II > III 
D)  II > III > I > IV 
E)  III > I > II > IV

Question 10

Which reagent will distinguish between C6H5NH2 and (C6H5)2NH?

Accepted Answer

A)  HCl (aq) 
B)  NaOH 
C)  C6H5SO2Cl/OH-,then H3O+ 
D)  Br2/CCl4 
E)  KMnO4 
A)  HCl (aq) 
B)  NaOH 
C)  C6H5SO2Cl/OH-,then H3O+ 
D)  Br2/CCl4 
E)  KMnO4

Question 11

What would be the product of the following reaction sequence?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 12

List the following compounds in order of increasing basicity (least to most),and explain your reasoning.

Accepted Answer

I < II < III
Reasoning - basicity follow

Question 13

Outline the steps involved in the Gabriel synthesis of allyl amine.

Accepted Answer

The answer of Outline the steps involved in the Gabriel...

Question 14

List the following compounds in order of increasing electronegativity (least to most)of the nitrogen atom,and explain your reasoning.

Accepted Answer

III < II < I
Reasoning - Electronegativi

Question 15

Which of the following bases has a conjugate acid with the smallest pKa?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  Cannot be determined from information given 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  Cannot be determined from information given

Question 16

Which is the major product of the following reaction?   2

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Question 17

How would one carry out the following transformation?

Accepted Answer

A)  NaNO2,HCl,0-5 $\degree$C;then HNO3 
B)  NaNO2,HCl,0-5 $\degree$C;then H3PO2 
C)  NaNO2,HCl,0-5 $\degree$C;then H2,Ni 
D)  C6H5SO2Cl,OH-;then HCl 
E)  NaH,DMSO 
A)  NaNO2,HCl,0-5 $\degree$C;then HNO3 
B)  NaNO2,HCl,0-5 $\degree$C;then H3PO2 
C)  NaNO2,HCl,0-5 $\degree$C;then H2,Ni 
D)  C6H5SO2Cl,OH-;then HCl 
E)  NaH,DMSO

Question 18

What would be the product of the following reaction sequence?

Accepted Answer

A)  p-bromobenzamide 
B)  p-bromobenzaldehyde oxime 
C)  p-bromobenzenesulfonamide 
D)  p-bromoaniline 
E)  4-bromo-3-chlorobenzoic acid 
A)  p-bromobenzamide 
B)  p-bromobenzaldehyde oxime 
C)  p-bromobenzenesulfonamide 
D)  p-bromoaniline 
E)  4-bromo-3-chlorobenzoic acid

Question 19

Which reagent would serve as the basis for a simple chemical test that would distinguish between the pair of compounds listed below?

Accepted Answer

A)  AgNO3 in H2O 
B)  Dilute NaHCO3 
C)  Dilute NaOH 
D)  C6H5SO2Cl/OH-,then H3O+ 
E)  Dilute HCl 
A)  AgNO3 in H2O 
B)  Dilute NaHCO3 
C)  Dilute NaOH 
D)  C6H5SO2Cl/OH-,then H3O+ 
E)  Dilute HCl

Question 20

Which of these would be predicted to have the smallest pKa?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  V 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  V

Exam 20: Amines

Arrange the following amines in order of decreasing basicity (most to least)in aqueous solution: NH3 CH3CH2CH2NH2 (CH3CH2CH2)2NH (CH3CH2CH2)3N I II III IV

Arrange the following amines in order of increasing basicity (least to most)in aqueous solution: NH3 CH3CH2CH2NH2 (CH3CH2CH2)2NH (CH3CH2CH2)3N I II III IV

Which of the following bases has a conjugate acid with the smallest pKa?

Arylamines are less basic than alkylamines because of _______________.

What is the final product of the reaction sequence:

Which combination of reactants will not produce ?

Which is not an intermediate in the Hofmann degradation reaction?

What compound is likely to be obtained via the following reaction sequence?

Arrange the following amines in order of decreasing basicity (most to least)in the gas phase: NH3 CH3CH2CH2NH2 (CH3CH2CH2)2NH (CH3CH2CH2)3N I II III IV

Which reagent will distinguish between C6H5NH2 and (C6H5)2NH?

What would be the product of the following reaction sequence?

List the following compounds in order of increasing basicity (least to most),and explain your reasoning.

Outline the steps involved in the Gabriel synthesis of allyl amine.

List the following compounds in order of increasing electronegativity (least to most)of the nitrogen atom,and explain your reasoning.

Which of the following bases has a conjugate acid with the smallest pKa?

Which is the major product of the following reaction? 2

How would one carry out the following transformation?

What would be the product of the following reaction sequence?

Which reagent would serve as the basis for a simple chemical test that would distinguish between the pair of compounds listed below?

Which of these would be predicted to have the smallest pKa?

Carbon Compounds and Chemical Bonds

Representative Carbon Compounds: Functional Groups, Intermolecular Forces, and Infrared Ir Spectroscopy

An Introduction to Organic Reactions: Acids and Bases

Alkanes: Nomenclature, Conformational Analysis, and an Introduction to Synthesis

Stereochemistry: Chiral Molecules

Ionic Reactions - Nucleophilic Substitution and Elimination Reactions of Alkyl Halides

Alkenes and Alkynes I: Properties and Synthesis, Elimination Reactions of Alkyl Halides

Alkenes and Alkynes Ii: Addition Reactions

Nuclear Magnetic Resonance and Mass Spectrometry: Tools for Structure Determination

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds Oxidation-Reduction and Organometallic Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group

Aldehydes and Ketones Ii Aldol Reactions

Carboxylic Acids and Their Derivatives Nucleophilic Addition - Elimination at the Acyl Carbon

Synthesis and Reactions of Beta-Dicarbonyl Compounds: More Chemistry of Enolate Ions

Phenols and Aryl Halides: Nucleophilic Aromatic Substitution

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

Arrange the following amines in order of decreasing basicity (most to least)in aqueous solution: NH₃ CH₃CH₂CH₂NH₂ (CH₃CH₂CH₂)₂NH (CH₃CH₂CH₂)₃N I II III IV

Arrange the following amines in order of increasing basicity (least to most)in aqueous solution: NH₃ CH₃CH₂CH₂NH₂ (CH₃CH₂CH₂)₂NH (CH₃CH₂CH₂)₃N I II III IV

Arrange the following amines in order of decreasing basicity (most to least)in the gas phase: NH₃ CH₃CH₂CH₂NH₂ (CH₃CH₂CH₂)₂NH (CH₃CH₂CH₂)₃N I II III IV

Which reagent will distinguish between C₆H₅NH₂ and (C₆H₅)₂NH?