Question 1

Provide the major organic product of the reaction shown below.

Accepted Answer

The answer of Provide the major organic product of the...

Question 2

Name the following compound.

Accepted Answer

p-chlorobe

Question 3

Which is more soluble in water, 2-butanone or n-hexane? Explain.

Accepted Answer

2-Butanone is more soluble in water. The

Question 4

Which compound will show an intense peak in the mass spectrum at m/z 58?

Accepted Answer

A)  CH3COCH2CH2CH3 
B)  (CH3)2CHCOCH3 
C)  CH3CH2COCH2CH3 
D)  (CH3)3CCHO 
E)  (CH3)3CCOCH3 
A)  CH3COCH2CH2CH3 
B)  (CH3)2CHCOCH3 
C)  CH3CH2COCH2CH3 
D)  (CH3)3CCHO 
E)  (CH3)3CCOCH3

Question 5

Provide the IUPAC name for the following compound.

Accepted Answer

6-hydroxy-

Question 6

Which of the following is also known as a Schiff base?

Accepted Answer

A)  an imine 
B)  a cyanohydrin 
C)  a hydrate 
D)  sodium hydroxide 
E)  an aldehyde 
A)  an imine 
B)  a cyanohydrin 
C)  a hydrate 
D)  sodium hydroxide 
E)  an aldehyde

Question 7

Predict the major organic product of the following reaction:

Accepted Answer

The answer of Predict the major organic product of the...

Question 8

What reagents can be used to convert 1-hexyne into 2-hexanone?

Accepted Answer

A)  1. Sia2BH; 2. H2O2, NaOH 
B)  Hg2+, H2SO4, H2O 
C)  1. O3; 2. (CH3)2S 
D)  1. CH3MgBr; 2. CO2 
E)  1. H2, Ni; 2. Na2Cr2O7, H2SO4 
A)  1. Sia2BH; 2. H2O2, NaOH 
B)  Hg2+, H2SO4, H2O 
C)  1. O3; 2. (CH3)2S 
D)  1. CH3MgBr; 2. CO2 
E)  1. H2, Ni; 2. Na2Cr2O7, H2SO4

Question 9

Another name for β-methoxybutyraldehyde is ________.

Accepted Answer

A)  2-methoxypropanal 
B)  3-methoxypropanal 
C)  2-methoxybutanal 
D)  3-methoxybutanal 
E)  2-methoxypentanal 
A)  2-methoxypropanal 
B)  3-methoxypropanal 
C)  2-methoxybutanal 
D)  3-methoxybutanal 
E)  2-methoxypentanal

Question 10

Provide the major organic product of the reaction shown below.

Accepted Answer

The answer of Provide the major organic product of the...

Question 11

Which series of reactions described below, if any, will result in the formation of 2-methylpentan-3-one starting with 1-propanol?

Accepted Answer

A)  1. (CH3)2CHMgBr/ diethyl ether
2) dilute H3O+
3) PCC 
B)  1. Na2Cr2O7/H2SO4 and heat
2) SOCl2
3) 2 (CH3)2CHMgBr/ diethyl ether
4) H3O+ 
C)  1. Na2Cr2O7/H2SO4 and heat
2) (CH3)2CHMgBr/ diethyl ether
3) dilute H3O+
4) LiAlH4 
D)  1. PCC
2) (CH3)2CHLi/ diethyl ether
3) dilute H3O+
4) Na2Cr2O7/H2SO4 and heat 
E)  none of the above 
A)  1. (CH3)2CHMgBr/ diethyl ether
2) dilute H3O+
3) PCC 
B)  1. Na2Cr2O7/H2SO4 and heat
2) SOCl2
3) 2 (CH3)2CHMgBr/ diethyl ether
4) H3O+ 
C)  1. Na2Cr2O7/H2SO4 and heat
2) (CH3)2CHMgBr/ diethyl ether
3) dilute H3O+
4) LiAlH4 
D)  1. PCC
2) (CH3)2CHLi/ diethyl ether
3) dilute H3O+
4) Na2Cr2O7/H2SO4 and heat 
E)  none of the above

Question 12

Provide a detailed, stepwise mechanism for the base-catalyzed hydration of 2-butanone.

Accepted Answer

The answer of Provide a detailed, stepwise mechanism for the...

Question 13

The reagent which converts a carbonyl group of a ketone into a methylene group is ________.

Accepted Answer

A)  Na, NH3, CH3CH2OH 
B)  LiAlH4 
C)  NaBH4, CH3CH2OH 
D)  Zn(Hg), conc. HCl 
E)  LiAlH[OC(CH3)3]3 
A)  Na, NH3, CH3CH2OH 
B)  LiAlH4 
C)  NaBH4, CH3CH2OH 
D)  Zn(Hg), conc. HCl 
E)  LiAlH[OC(CH3)3]3

Question 14

The strongest absorptions in the UV spectra of aldehydes and ketones are ones which result from ________ electronic transitions.

Accepted Answer

A)  σ to σ* 
B)  σ to π* 
C)  n to π* 
D)  π to π* 
E)  π to σ* 
A)  σ to σ* 
B)  σ to π* 
C)  n to π* 
D)  π to π* 
E)  π to σ*

Question 15

Oxidation of a 3° alcohol with chromic acid results in the production of ________.

Accepted Answer

A)  an ester 
B)  a ketone 
C)  an aldehyde 
D)  an ether 
E)  none of the above 
A)  an ester 
B)  a ketone 
C)  an aldehyde 
D)  an ether 
E)  none of the above

Question 16

Propose a sequence of steps to carry out the following conversion.

Accepted Answer

1) HOCH₂CH₂OH, H⁺ 2) Na

Question 17

Show how the following reaction may be accomplished by filling in the correct reagents.

Accepted Answer

1) LDA or

Question 18

Provide the major organic product of the reaction shown below.

Accepted Answer

The answer of Provide the major organic product of the...

Question 19

Provide the major organic product of the following reaction.

Accepted Answer

The answer of Provide the major organic product of the...

Question 20

Provide the structure of the hydrate of cyclopentanone.

Accepted Answer

The answer of Provide the structure of the hydrate of...

Exam 18: Ketones and Aldehydes

Provide the major organic product of the reaction shown below.

Name the following compound.

Which is more soluble in water, 2-butanone or n-hexane? Explain.

Which compound will show an intense peak in the mass spectrum at m/z 58?

Provide the IUPAC name for the following compound.

Which of the following is also known as a Schiff base?

Predict the major organic product of the following reaction:

What reagents can be used to convert 1-hexyne into 2-hexanone?

Another name for β-methoxybutyraldehyde is ________.

Provide the major organic product of the reaction shown below.

Which series of reactions described below, if any, will result in the formation of 2-methylpentan-3-one starting with 1-propanol?

Provide a detailed, stepwise mechanism for the base-catalyzed hydration of 2-butanone.

The reagent which converts a carbonyl group of a ketone into a methylene group is ________.

The strongest absorptions in the UV spectra of aldehydes and ketones are ones which result from ________ electronic transitions.

Oxidation of a 3° alcohol with chromic acid results in the production of ________.

Propose a sequence of steps to carry out the following conversion.

Show how the following reaction may be accomplished by filling in the correct reagents.

Provide the major organic product of the reaction shown below.

Provide the major organic product of the following reaction.

Provide the structure of the hydrate of cyclopentanone.

Structure and Bonding

Acids and Bases; Functional Groups

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides; Nucleophilic Substitution

Structure and Synthesis of Alkenes; Elimination

Reactions of Alkenes

Structure and Synthesis of Alcohols

Reactions of Alcohols

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Ethers, Epoxides, and Thioethers

Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Aromatic Compounds

Reactions of Aromatic Compounds

Amines

Carboxylic Acids

Carboxylic Acid Derivatives

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

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