Question 1

Which compound is a hemiacetal?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  All of the above 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  All of the above A

Question 2

A good synthesis of

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  All of these are equally useful. 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  All of these are equally useful. C

Question 3

The conversion of a cis epoxide to a trans alkene using triphenylphosphine is an example
of a ______________reaction.

Accepted Answer

stereospecific

Question 4

A good synthesis of

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  All of these are equally useful. 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  All of these are equally useful.

Question 5

Which of the compounds listed below would you expect to have the highest boiling point? (They all have approximately the same molecular weight. )

Accepted Answer

A)  Pentane 
B)  1-Butanol 
C)  Butanal 
D)  1-Fluorobutane 
E)  Diethylether 
A)  Pentane 
B)  1-Butanol 
C)  Butanal 
D)  1-Fluorobutane 
E)  Diethylether

Question 6

Which reaction sequence would be used to prepare

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  All of the above would yield the product. 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  All of the above would yield the product.

Question 7

Select the structure of the major product in the following reaction.

Accepted Answer

A)  cyclopentanol 
B)  1-cyclopentylcyclopentane 
C)  cyclopentanone 
D)  cyclopentene 
E)  1-(1-hydroxycyclopentyl)-1-hydroxycyclopentane 
A)  cyclopentanol 
B)  1-cyclopentylcyclopentane 
C)  cyclopentanone 
D)  cyclopentene 
E)  1-(1-hydroxycyclopentyl)-1-hydroxycyclopentane

Question 8

What is the correct structure for 3-methyl-5-(4-chlorophenyl)hexanal?

Accepted Answer

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

Question 9

Select the structure of the major product in the following reaction.

Accepted Answer

A)  3-Methylhexanal 
B)  4-Methyl-1-hexanol 
C)  4-Methylhexanal 
D)  4,10-Dimethyldodecane-6,7-dione 
E)  4,10-Dimethyldodecane-6,7-diol 
A)  3-Methylhexanal 
B)  4-Methyl-1-hexanol 
C)  4-Methylhexanal 
D)  4,10-Dimethyldodecane-6,7-dione 
E)  4,10-Dimethyldodecane-6,7-diol

Question 10

Suggest a synthetic strategy for the synthesis of 3-heptanone from 1-butene.

Accepted Answer

The answer of Suggest a synthetic strategy for the synthesis...

Question 11

What is the correct IUPAC name for the following compound?

Accepted Answer

A)  2-Methyl-5-heptanone 
B)  7-Methyl-4-octanone 
C)  6-Isopropyl-4-octanone 
D)  Isobutyl propyl ketone 
E)  1,1-Dimethyl-4-heptanone 
A)  2-Methyl-5-heptanone 
B)  7-Methyl-4-octanone 
C)  6-Isopropyl-4-octanone 
D)  Isobutyl propyl ketone 
E)  1,1-Dimethyl-4-heptanone

Question 12

Which is the IUPAC name for the structure shown below?

Accepted Answer

A)  5-Cyclohexyl-2-hexanal 
B)  5-Cyclohexyl-2-hexanone 
C)  5-Cyclohexyl-5-methyl-2-pentanone 
D)  5-(1-Methylcyclohexyl)-2-pentanone 
E)  4-(1-Methylcyclohexyl)-2-butanone 
A)  5-Cyclohexyl-2-hexanal 
B)  5-Cyclohexyl-2-hexanone 
C)  5-Cyclohexyl-5-methyl-2-pentanone 
D)  5-(1-Methylcyclohexyl)-2-pentanone 
E)  4-(1-Methylcyclohexyl)-2-butanone

Question 13

A compound with two OR groups attached to the same carbon is known as a(n)_________.

Accepted Answer

The answer of A compound with two OR groups attached...

Question 14

The 13C NMR spectrum of a compound with formula C7H14O gives five signals.Which of these structures is a possible one for this compound?

Accepted Answer

A)  2-Heptanone 
B)  3-Heptanone 
C)  2,2-Dimethyl-3-pentanone 
D)  2,4-Dimethyl-3-pentanone 
E)  Two of the above 
A)  2-Heptanone 
B)  3-Heptanone 
C)  2,2-Dimethyl-3-pentanone 
D)  2,4-Dimethyl-3-pentanone 
E)  Two of the above

Question 15

What is the correct structure for 3-phenylpropanal?

Accepted Answer

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

Question 16

A good synthesis of

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  All of these are equally useful. 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  All of these are equally useful.

Question 17

What is the correct structure for 2,3-dimethyl-2-hepten-4-one?

Accepted Answer

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

Question 18

The 1H NMR spectrum of a compound with formula C7H14O gives two signals.Which of these structures is a possible one for this compound?

Accepted Answer

A)  2-Heptanone 
B)  3-Heptanone 
C)  2,4-Dimethyl-3-pentanone 
D)  2,2-Dimethyl-3-pentanone 
E)  Two of the above 
A)  2-Heptanone 
B)  3-Heptanone 
C)  2,4-Dimethyl-3-pentanone 
D)  2,2-Dimethyl-3-pentanone 
E)  Two of the above

Question 19

Which is the proper name for the structure shown?

Accepted Answer

A)  2-Chloro-5-aldehydotoluene 
B)  6-Chloro-3-aldehydotoluene 
C)  2-Methyl-4-aldehydochlorobenzene 
D)  4-Chloro-3-methylbenzaldehyde 
E)  4-Methyl-5-chloro-2-benzaldehyde 
A)  2-Chloro-5-aldehydotoluene 
B)  6-Chloro-3-aldehydotoluene 
C)  2-Methyl-4-aldehydochlorobenzene 
D)  4-Chloro-3-methylbenzaldehyde 
E)  4-Methyl-5-chloro-2-benzaldehyde

Question 20

What is the major 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

Exam 16: Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group

Which compound is a hemiacetal?

A good synthesis of

The conversion of a cis epoxide to a trans alkene using triphenylphosphine is an example of a ______________reaction.

A good synthesis of

Which of the compounds listed below would you expect to have the highest boiling point? (They all have approximately the same molecular weight. )

Which reaction sequence would be used to prepare

Select the structure of the major product in the following reaction.

What is the correct structure for 3-methyl-5-(4-chlorophenyl)hexanal?

Select the structure of the major product in the following reaction.

Suggest a synthetic strategy for the synthesis of 3-heptanone from 1-butene.

What is the correct IUPAC name for the following compound?

Which is the IUPAC name for the structure shown below?

A compound with two OR groups attached to the same carbon is known as a(n)_________.

The 13C NMR spectrum of a compound with formula C7H14O gives five signals.Which of these structures is a possible one for this compound?

What is the correct structure for 3-phenylpropanal?

A good synthesis of

What is the correct structure for 2,3-dimethyl-2-hepten-4-one?

The 1H NMR spectrum of a compound with formula C7H14O gives two signals.Which of these structures is a possible one for this compound?

Which is the proper name for the structure shown?

What is the major product of the following reaction sequence?

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 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

Amines

Phenols and Aryl Halides: Nucleophilic Aromatic Substitution

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

The ¹³C NMR spectrum of a compound with formula C₇H₁₄O gives five signals.Which of these structures is a possible one for this compound?

The ¹H NMR spectrum of a compound with formula C₇H₁₄O gives two signals.Which of these structures is a possible one for this compound?