Question 1

Draw the structure corresponding to the following name:
(4Z,3S)-2,4,7-trimethyl-3-amino-4-octene

Accepted Answer

The answer of Draw the structure corresponding to the following...

Question 2

Which product could not be formed during the following reaction?

Accepted Answer

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

Question 3

You have just completed an experiment involving the reduction of m-nitrobenzoic acid with Fe/HCl.In order to determine if your reaction has worked as planned,you have obtained the 1H NMR of your crude product.What will you scrutinize the spectrum for,in order to help you make this assessment?

Accepted Answer

The appearance of 2 new N-H signals,in the range of about 2-6 ppm will be indicative of successful reduction of the -NO₂ group to the -NH₂ group.These signals are characteristically somewhat broad,and should disappear (or decrease markedly)if the spectrum is rerun with an added drop of D₂O to the original sample prepared for obtaining the ¹H NMR.The rest of the signals are likely to remain more or less similar,with some changes in chemical shift likely (probably upfield shifts),since the -NO₂ group is electron-withdrawing,while the -NH₂ group is electron-donating.

Question 4

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 5

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 6

What type of amine is pyrrole?

Accepted Answer

A)  Primary 
B)  Secondary 
C)  Tertiary 
D)  Quaternary 
E)  None of these 
A)  Primary 
B)  Secondary 
C)  Tertiary 
D)  Quaternary 
E)  None of these

Question 7

The overall conversion RBr --$\rightarrow$RCH2NH2 can be accomplished by successive application of which of these sets of reagents?

Accepted Answer

A)  Mg,ether;then NH3 
B)  NaN3;then LiAlH4,ether 
C)  NaCN;then LiAlH4,ether 
D)  H2C=O;then NH3 
E)  H2NOH;then LiAlH4,ether 
A)  Mg,ether;then NH3 
B)  NaN3;then LiAlH4,ether 
C)  NaCN;then LiAlH4,ether 
D)  H2C=O;then NH3 
E)  H2NOH;then LiAlH4,ether

Question 8

Which of these is the strongest acid?

Accepted Answer

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

Question 9

What reagent can effect the following transformation?

Accepted Answer

A)  Fe/HCl;then OH- 
B)  NH2Cl 
C)  H3PO2 
D)  CuCN 
E)  HONO;then NH3 
A)  Fe/HCl;then OH- 
B)  NH2Cl 
C)  H3PO2 
D)  CuCN 
E)  HONO;then NH3

Question 10

Which of these is properly termed a "quaternary ammonium salt"?

Accepted Answer

A)  (CH3)3CCH2CH2NH3+ Cl - 
B)  (CH3CH2CH(CH3)CH2)2NH2+ Cl - 
C)  (CH3CH2CH2)3NH+ Cl - 
D)  (CH3CH2CH2)4N+ Cl - 
E)  None of these 
A)  (CH3)3CCH2CH2NH3+ Cl - 
B)  (CH3CH2CH(CH3)CH2)2NH2+ Cl - 
C)  (CH3CH2CH2)3NH+ Cl - 
D)  (CH3CH2CH2)4N+ Cl - 
E)  None of these

Question 11

Amines are known to rapidly undergo pyramidal inversion at ordinary temperatures,preventing the resolution of enantiomeric forms when the amine is a chirality center.The proposed transition state of the inversion process is shown below.Using an orbital diagram,illustrate the hybridization at nitrogen for this proposed transition state.

Accepted Answer

In the trigonal pyramidal form,nitrogen

Question 12

What type of amine is N-methyl-2-methyl-3-hexanamine?

Accepted Answer

A)  Primary 
B)  Secondary 
C)  Tertiary 
D)  Quaternary 
E)  None of these 
A)  Primary 
B)  Secondary 
C)  Tertiary 
D)  Quaternary 
E)  None of these

Question 13

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

Accepted Answer

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

Question 14

Outline the steps involved in the Gabriel synthesis of allylamine.

Accepted Answer

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

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 would be predicted to have the largest pKa?

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 final product is expected when toluene is subjected to the following reaction sequence? i)KMnO4,NaOH;ii)H3O+ ( product = C7H6O2);iii)SOCl2;
Iv)NH3 (product = C7H7NO);v)Br2,NaOH

Accepted Answer

A)  C6H5CONH2 
B)  C6H5CH2NH2 
C)  p-CH3C6H4SO2NH2 
D)  p-CH3C6H4NH2 
E)  C6H5NH2 
A)  C6H5CONH2 
B)  C6H5CH2NH2 
C)  p-CH3C6H4SO2NH2 
D)  p-CH3C6H4NH2 
E)  C6H5NH2

Question 18

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

Accepted Answer

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

Question 19

If the three alkyl groups of a tertiary amine are all different,the amine will be chiral.In practice,however,it is virtually impossible to separate the two enantiomers,because they interconvert rapidly through a process called _________________.

Accepted Answer

nitrogen i

Question 20

-In aqueous solution,which of the following bases as the conjugate acid possesses the largest value for pKa?

Accepted Answer

A)  C6H5NH2 
B)  NH3 
C)  (CH3CH2)3N 
D)  (CH3CH2)2NH 
E)  CH3CH2CH2NH2 
A)  C6H5NH2 
B)  NH3 
C)  (CH3CH2)3N 
D)  (CH3CH2)2NH 
E)  CH3CH2CH2NH2

Exam 20: Amines

Draw the structure corresponding to the following name: (4Z,3S)-2,4,7-trimethyl-3-amino-4-octene

Which product could not be formed during the following reaction?

You have just completed an experiment involving the reduction of m-nitrobenzoic acid with Fe/HCl.In order to determine if your reaction has worked as planned,you have obtained the 1H NMR of your crude product.What will you scrutinize the spectrum for,in order to help you make this assessment?

What would be the product of the following reaction sequence?

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

What type of amine is pyrrole?

The overall conversion RBr -- →\rightarrow→ RCH2NH2 can be accomplished by successive application of which of these sets of reagents?

Which of these is the strongest acid?

What reagent can effect the following transformation?

Which of these is properly termed a "quaternary ammonium salt"?

What type of amine is N-methyl-2-methyl-3-hexanamine?

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

Outline the steps involved in the Gabriel synthesis of allylamine.

What would be the product of the following reaction sequence?

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

What final product is expected when toluene is subjected to the following reaction sequence? i)KMnO4,NaOH;ii)H3O+ ( product = C7H6O2);iii)SOCl2; Iv)NH3 (product = C7H7NO);v)Br2,NaOH

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

If the three alkyl groups of a tertiary amine are all different,the amine will be chiral.In practice,however,it is virtually impossible to separate the two enantiomers,because they interconvert rapidly through a process called _________________.

-In aqueous solution,which of the following bases as the conjugate acid possesses the largest value for 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

You have just completed an experiment involving the reduction of m-nitrobenzoic acid with Fe/HCl.In order to determine if your reaction has worked as planned,you have obtained the ¹H NMR of your crude product.What will you scrutinize the spectrum for,in order to help you make this assessment?

The overall conversion RBr -- $\rightarrow$ RCH₂NH₂ can be accomplished by successive application of which of these sets of reagents?

What final product is expected when toluene is subjected to the following reaction sequence? i)KMnO₄,NaOH;ii)H₃O⁺ ( product = C₇H₆O₂);iii)SOCl₂; Iv)NH₃ (product = C₇H₇NO);v)Br₂,NaOH

-In aqueous solution,which of the following bases as the conjugate acid possesses the largest value for pK_a?