Question 1

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)  HONO,0-5°C then $\beta$-naphthol 
C)  Dilute NaOH 
D)  C6H5SO2Cl and OH- in H2O 
E)  Dilute HCl 
A)  AgNO3 in H2O 
B)  HONO,0-5°C then $\beta$-naphthol 
C)  Dilute NaOH 
D)  C6H5SO2Cl and OH- in H2O 
E)  Dilute HCl

Question 2

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 3

Which is a correct common name for the following substance?

Accepted Answer

A)  Ethylethylisobutylamine 
B)  Diethylisobutylamine 
C)  sec-Butyldiethylamine 
D)  Ethylethyl-sec-butylamine 
E)  2-Diethylaminobutane 
A)  Ethylethylisobutylamine 
B)  Diethylisobutylamine 
C)  sec-Butyldiethylamine 
D)  Ethylethyl-sec-butylamine 
E)  2-Diethylaminobutane

Question 4

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

Accepted Answer

A)  p-Methylaniline 
B)  p-Methoxyaniline 
C)  Hexylamine 
D)  p-Nitroaniline 
E)  Dipropylamine 
A)  p-Methylaniline 
B)  p-Methoxyaniline 
C)  Hexylamine 
D)  p-Nitroaniline 
E)  Dipropylamine

Question 5

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 6

Consider the synthesis below.What is reagent "Z"?

Accepted Answer

A)  CuCl 
B)  CuCl2 
C)  NaCl 
D)  KCl 
E)  HCl/heat 
A)  CuCl 
B)  CuCl2 
C)  NaCl 
D)  KCl 
E)  HCl/heat

Question 7

What final product is expected from 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 8

The reaction of which of these compounds with nitrous acid results in a stable N-nitroso compound?

Accepted Answer

A)  C6H5NH2 
B)  C6H5N(CH3)2 
C)  CH3CH2CH2CH2CH2NH2  
D)  C6H5NHCH3 
E)  CH3CH2CONH2 
A)  C6H5NH2 
B)  C6H5N(CH3)2 
C)  CH3CH2CH2CH2CH2NH2  
D)  C6H5NHCH3 
E)  CH3CH2CONH2

Question 9

Which of the following compounds would be the strongest base?

Accepted Answer

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

Question 10

What is the final product,C?

Accepted Answer

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

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

Arrange the following compounds in order of increasing basicity (least to most)in aqueous solution:

Accepted Answer

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

Question 13

Outline the steps involved in the Gabriel synthesis of 3-amino-2-methylpentane.

Accepted Answer

@#IMG-DLM& 3-amino-2

Question 14

Which would be the weakest base?

Accepted Answer

A)  p-Methylaniline 
B)  p-Methoxyaniline 
C)  Hexylamine 
D)  p-Nitroaniline 
E)  Dipropylamine 
A)  p-Methylaniline 
B)  p-Methoxyaniline 
C)  Hexylamine 
D)  p-Nitroaniline 
E)  Dipropylamine

Question 15

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 16

Which of these compounds is soluble in dilute sodium hydroxide solution?

Accepted Answer

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

Question 17

What is the chief product of the Hofmann elimination reaction applied to the compound shown?

Accepted Answer

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

Question 18

Consider the synthesis below.What is reagent A?

Accepted Answer

A)  H3PO2 
B)  HCN 
C)  P4O10 
D)  CuCN 
E)  CuCl2 
A)  H3PO2 
B)  HCN 
C)  P4O10 
D)  CuCN 
E)  CuCl2

Question 19

Which of these could be resolved into separate enantiomers?

Accepted Answer

A)  4-Methyl-1-pentanamine 
B)  4-Methyl-2-pentanamine 
C)  N-Methyl-1-butanamine 
D)  N,N-Dimethyl-1-propanamine 
E)  N-Butyltrimethylammonium bromide 
A)  4-Methyl-1-pentanamine 
B)  4-Methyl-2-pentanamine 
C)  N-Methyl-1-butanamine 
D)  N,N-Dimethyl-1-propanamine 
E)  N-Butyltrimethylammonium bromide

Question 20

Using resonance theory,explain why guanidine is one of the strongest organic bases.

Accepted Answer

@#IMG-DLM& The protonated form (conjugat

Exam 20: Amines

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

Which is the major product of the following reaction? 2

Which is a correct common name for the following substance?

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

What would be the product of the following reaction sequence?

Consider the synthesis below.What is reagent "Z"?

What final product is expected from the following reaction sequence?

The reaction of which of these compounds with nitrous acid results in a stable N-nitroso compound?

Which of the following compounds would be the strongest base?

What is the final product,C?

What would be the product of the following reaction sequence?

Arrange the following compounds in order of increasing basicity (least to most)in aqueous solution:

Outline the steps involved in the Gabriel synthesis of 3-amino-2-methylpentane.

Which would be the weakest base?

What would be the product of the following reaction sequence?

Which of these compounds is soluble in dilute sodium hydroxide solution?

What is the chief product of the Hofmann elimination reaction applied to the compound shown?

Consider the synthesis below.What is reagent A?

Which of these could be resolved into separate enantiomers?

Using resonance theory,explain why guanidine is one of the strongest organic bases.

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

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