Question 1

Provide the proper IUPAC name for CH3CHOHCH2COCH2C(CH3)2CH2CH3.

Accepted Answer

2-hydroxy-

Question 2

Provide the major organic product which results when PhCH2CH2CO2H is treated with excess butyllithium followed by H3O+.

Accepted Answer

Question 3

When a carbonyl is part of a conjugated π-network, the C-O stretch:

Accepted Answer

A)  has a higher frequency than in a nonconjugated system. 
B)  has a lower frequency than in a nonconjugated system. 
C)  always occurs at 1710 cm-1. 
D)  occurs around 2700 cm-1. 
E)  cannot be distinguished from the C-O stretch in a nonconjugated system. 
A)  has a higher frequency than in a nonconjugated system. 
B)  has a lower frequency than in a nonconjugated system. 
C)  always occurs at 1710 cm-1. 
D)  occurs around 2700 cm-1. 
E)  cannot be distinguished from the C-O stretch in a nonconjugated system.

Question 4

Provide the structure of the diethyl acetal of butanal.

Accepted Answer

The answer of Provide the structure of the diethyl acetal...

Question 5

Provide the proper IUPAC name for CH3OCH2CH2CH(CH3)CHO.

Accepted Answer

4-methoxy-

Question 6

Propose a synthesis of 3-heptanone from propanal.

Accepted Answer

1. CH₃CH₂CH₂C

Question 7

Which sequence ranks the following carbonyl compounds in order of increasing rate of nucleophilic addition?

Accepted Answer

A)  2 < 3 < 1 
B)  3 < 2 < 1 
C)  2 < 1 < 3 
D)  1 < 3 < 2 
A)  2 < 3 < 1 
B)  3 < 2 < 1 
C)  2 < 1 < 3 
D)  1 < 3 < 2

Question 8

Provide a detailed, stepwise mechanism for the acid-catalyzed condensation reaction between benzaldehyde and methylamine.

Accepted Answer

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

Question 9

In the mass spectrum of 3,3-dimethyl-2-butanone, the base peak will occur at m/z ________.

Accepted Answer

A)  43 
B)  58 
C)  84 
D)  85 
E)  100 
A)  43 
B)  58 
C)  84 
D)  85 
E)  100

Question 10

Through what sequence of steps can toluene be converted into PhCH2PPh3+Br-?

Accepted Answer

1. Br₂, hν

Question 11

Provide the IUPAC name for the following compound.

Accepted Answer

6-hydroxy-

Question 12

Provide the structure of cyclohexanecarbaldehyde.

Accepted Answer

The answer of Provide the structure of cyclohexanecarbaldehyde....

Question 13

By which single reaction can benzene be readily converted into acetophenone?

Accepted Answer

CH₃COCl, AlCl₃ - a Fri

Question 14

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 15

Consider the equilibrium of each of the carbonyl compounds with HCN to produce cyanohydrins. Which is the correct ranking of compounds in order of increasing Keq for this equilibrium?

Accepted Answer

A)  H2CO 3CHO 3CHO 2CO 
C)  cyclohexanone 2CO 3CHO 
D)  cyclohexanone 3CHO 2CO 
E)  2-methylcyclohexanone 3CHO 2CO 
A)  H2CO 3CHO 3CHO 2CO 
C)  cyclohexanone 2CO 3CHO 
D)  cyclohexanone 3CHO 2CO 
E)  2-methylcyclohexanone 3CHO 2CO

Question 16

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 17

Give an IUPAC name to the following compound. Be sure to include configurational information in the name.

Accepted Answer

(Z)-4-oxo-

Question 18

Beginning with 1,3-dithiane, propose a synthesis of 4-heptanone.

Accepted Answer

1. BuLi 2. CH₃CH₂CH₂Br

Question 19

Oxidation of a 1° 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 20

Conversion of aldehydes and ketones to imines is an acid-catalyzed process. Explain why this conversion is actually hindered by the presence of too much acid.

Accepted Answer

At very low pH, much

Exam 18: Ketones and Aldehydes

Provide the proper IUPAC name for CH3CHOHCH2COCH2C(CH3)2CH2CH3.

Provide the major organic product which results when PhCH2CH2CO2H is treated with excess butyllithium followed by H3O+.

When a carbonyl is part of a conjugated π-network, the C-O stretch:

Provide the structure of the diethyl acetal of butanal.

Provide the proper IUPAC name for CH3OCH2CH2CH(CH3)CHO.

Propose a synthesis of 3-heptanone from propanal.

Which sequence ranks the following carbonyl compounds in order of increasing rate of nucleophilic addition?

Provide a detailed, stepwise mechanism for the acid-catalyzed condensation reaction between benzaldehyde and methylamine.

In the mass spectrum of 3,3-dimethyl-2-butanone, the base peak will occur at m/z ________.

Through what sequence of steps can toluene be converted into PhCH2PPh3+Br-?

Provide the IUPAC name for the following compound.

Provide the structure of cyclohexanecarbaldehyde.

By which single reaction can benzene be readily converted into acetophenone?

Provide the major organic product of the reaction shown below.

Consider the equilibrium of each of the carbonyl compounds with HCN to produce cyanohydrins. Which is the correct ranking of compounds in order of increasing Keq for this equilibrium?

Provide the major organic product of the reaction shown below.

Give an IUPAC name to the following compound. Be sure to include configurational information in the name.

Beginning with 1,3-dithiane, propose a synthesis of 4-heptanone.

Oxidation of a 1° alcohol with chromic acid results in the production of ________.

Conversion of aldehydes and ketones to imines is an acid-catalyzed process. Explain why this conversion is actually hindered by the presence of too much acid.

Introduction and Review

Structure and Properties of Organic Molecules

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides: Nucleophilic Substitution and Elimination

Structure and Synthesis of Alkenes

Reactions of Alkenes

Alkynes

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

Filters

Provide the proper IUPAC name for CH₃CHOHCH₂COCH₂C(CH₃)₂CH₂CH₃.

Provide the major organic product which results when PhCH₂CH₂CO₂H is treated with excess butyllithium followed by H₃O⁺.

Provide the proper IUPAC name for CH₃OCH₂CH₂CH(CH₃)CHO.

Through what sequence of steps can toluene be converted into PhCH₂PPh₃⁺Br^-?

Consider the equilibrium of each of the carbonyl compounds with HCN to produce cyanohydrins. Which is the correct ranking of compounds in order of increasing K_eq for this equilibrium?