Question 1

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

Accepted Answer

CH₃COCl, AlCl₃ - a Fri

Question 2

Rank the following compounds in order of their propensity to become a hydrate in water (i.e., start with the least easy to hydrate: CH3COCH2CH3, H2CO, Cl3CCHO, and CH3CH2CHO.

Accepted Answer

CH₃COCH₂CH₃ <

Question 3

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 4

Beginning with sodium acetylide (NaCCH), propose a three-step synthesis of hexanal.

Accepted Answer

1. CH₃CH₂CH₂C

Question 5

Predict the major organic product of the following reaction:

Accepted Answer

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

Question 6

Complete the following reaction by filling in the necessary reagents.

Accepted Answer

The answer of Complete the following reaction by filling in...

Question 7

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

Accepted Answer

1) HOCH₂CH₂O

Question 8

Which series of reactions described below will result in the formation of compound A, starting with compound B?

Accepted Answer

A)  1. HO-(CH2)2-OH /trace H3O+
2) DMSO (COCl2)/Et3N, CH2Cl2
3) MgBr-(CH2)2-CH3/diethyl ether
4) work-up with H3O+
5. PCC 
B)  1. PCC
2) SOCl2
3) LiCu-((CH2)2-CH3)2
4) work-up with H3O+ 
C)  1. Na2Cr2O7/H2SO4
2) SOCl2
3) 2 MgBr-(CH2)2-CH3/diethyl ether
4) work-up with H3O+ 
D)  both A and B 
E)  both B and C 
A)  1. HO-(CH2)2-OH /trace H3O+
2) DMSO (COCl2)/Et3N, CH2Cl2
3) MgBr-(CH2)2-CH3/diethyl ether
4) work-up with H3O+
5. PCC 
B)  1. PCC
2) SOCl2
3) LiCu-((CH2)2-CH3)2
4) work-up with H3O+ 
C)  1. Na2Cr2O7/H2SO4
2) SOCl2
3) 2 MgBr-(CH2)2-CH3/diethyl ether
4) work-up with H3O+ 
D)  both A and B 
E)  both B and C

Question 9

Through what sequence of steps can toluene be converted into

Accepted Answer

1) Br₂, hν

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

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 12

Provide the proper IUPAC name for PhCH2CH(CH3)CH2CH2CHO.

Accepted Answer

4-methyl-5

Question 13

How would you perform the following transformation?

Accepted Answer

A)  NaBH4 
B)  LiAlH4 
C)  1. DIBAL-H 2. H2O 
D)  1. SOCl2 2. LiAlH(O-t-Bu)3 
A)  NaBH4 
B)  LiAlH4 
C)  1. DIBAL-H 2. H2O 
D)  1. SOCl2 2. LiAlH(O-t-Bu)3

Question 14

In the proton NMR spectra of aldehydes and ketones, the protons bonded to carbons adjacent to the carbonyl group typically fall into which of the chemical shift ranges below?

Accepted Answer

A)  1.0-2.0 ppm 
B)  2.0-3.0 ppm 
C)  4.0-4.5 ppm 
D)  7.0-8.0 ppm 
E)  9.0-10.0 ppm 
A)  1.0-2.0 ppm 
B)  2.0-3.0 ppm 
C)  4.0-4.5 ppm 
D)  7.0-8.0 ppm 
E)  9.0-10.0 ppm

Question 15

Draw a mechanism for the following reaction.

Accepted Answer

The answer of Draw a mechanism for the following reaction....

Question 16

What reagent can be used to convert 2-methylbutan-1-ol into 2-methylbutanal?

Accepted Answer

A)  LiAlH4 
B)  Na2Cr2O7 
C)  O3 
D)  KMnO4 
E)  PCC 
A)  LiAlH4 
B)  Na2Cr2O7 
C)  O3 
D)  KMnO4 
E)  PCC

Question 17

Provide the major organic product of the following reaction.

Accepted Answer

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

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 structure of benzophenone.

Accepted Answer

The answer of Provide the structure of benzophenone....

Question 20

Provide the major organic product in the reaction shown below.

Accepted Answer

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

Exam 18: Ketones and Aldehydes

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

Rank the following compounds in order of their propensity to become a hydrate in water (i.e., start with the least easy to hydrate: CH3COCH2CH3, H2CO, Cl3CCHO, and CH3CH2CHO.

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

Beginning with sodium acetylide (NaCCH), propose a three-step synthesis of hexanal.

Predict the major organic product of the following reaction:

Complete the following reaction by filling in the necessary reagents.

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

Which series of reactions described below will result in the formation of compound A, starting with compound B?

Through what sequence of steps can toluene be converted into

Provide the major organic product of the reaction shown below.

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

Provide the proper IUPAC name for PhCH2CH(CH3)CH2CH2CHO.

How would you perform the following transformation?

In the proton NMR spectra of aldehydes and ketones, the protons bonded to carbons adjacent to the carbonyl group typically fall into which of the chemical shift ranges below?

Draw a mechanism for the following reaction.

What reagent can be used to convert 2-methylbutan-1-ol into 2-methylbutanal?

Provide the major organic product of the following reaction.

Provide the major organic product of the reaction shown below.

Provide the structure of benzophenone.

Provide the major organic product in the reaction shown below.

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

Filters

Rank the following compounds in order of their propensity to become a hydrate in water (i.e., start with the least easy to hydrate: CH₃COCH₂CH₃, H₂CO, Cl₃CCHO, and CH₃CH₂CHO.

Provide the proper IUPAC name for PhCH₂CH(CH₃)CH₂CH₂CHO.