Question 1

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 2

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 3

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 4

Provide the major organic product of the reaction of aniline with 3-pentanone.

Accepted Answer

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

Question 5

Which of the following correctly describes the bond angle and hybridizations present in formaldehyde?

Accepted Answer

A)  C, sp2; O, sp3; HCO, ~120° 
B)  C, sp2; O, sp2; HCO, ~120° 
C)  C, sp2; O, sp2; HCO, ~109.5° 
D)  C, sp3; O, sp2; HCO, ~109.5° 
E)  C, sp3; O, sp3; HCO, ~109.5° 
A)  C, sp2; O, sp3; HCO, ~120° 
B)  C, sp2; O, sp2; HCO, ~120° 
C)  C, sp2; O, sp2; HCO, ~109.5° 
D)  C, sp3; O, sp2; HCO, ~109.5° 
E)  C, sp3; O, sp3; HCO, ~109.5°

Question 6

Name the following compound.

Accepted Answer

p-chlorobe

Question 7

What compound is produced when 1,3-dithiane is subjected to the following sequence of reagents:
1. n-BuLi 2. CH3CH2Br 3. n-BuLi 4. (CH3)2CHCH2CH2I 5. HgCl2, H3O+?

Accepted Answer

Question 8

In carbon NMR, the carbon atom of the carbonyl group in aldehydes and ketones has a chemical shift of about:

Accepted Answer

A)  20 ppm. 
B)  40 ppm. 
C)  60 ppm. 
D)  120 ppm. 
E)  200 ppm. 
A)  20 ppm. 
B)  40 ppm. 
C)  60 ppm. 
D)  120 ppm. 
E)  200 ppm.

Question 9

Would you expect the carbonyl carbon of benzaldehyde to be more or less electrophilic than that of acetaldehyde? Explain using resonance structures.

Accepted Answer

The carbonyl carbon of benzald

Question 10

Complete the following reaction by filling in the correct reagents.

Accepted Answer

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

Question 11

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

Accepted Answer

4-methyl-5

Question 12

Provide the major organic product which results when pentanal is subjected to the following sequence of steps:

Accepted Answer

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

Question 13

Provide the single reagent necessary for the conversion of cyclobutanone to the compound shown below.

Accepted Answer

The answer of Provide the single reagent necessary for the...

Question 14

Provide the structure of benzophenone.

Accepted Answer

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

Question 15

Provide the structure of the semicarbazone derivative of 3-pentanone.

Accepted Answer

The answer of Provide the structure of the semicarbazone derivative...

Question 16

When HOCH2CH2CH2CH2COCH2CH2CH2CH2OH is heated in the presence of an acid catalyst, a reaction occurs. This product has the formula C9H16O2. Provide the structure of this product.

Accepted Answer

Question 17

Which would be more appropriate as the reduction in the following sequence, a Clemmensen or a Wolff-Kishner? Explain.

Accepted Answer

Wolff-Kishner. The acidic cond

Question 18

Which of the following represents the correct ranking in terms of increasing boiling point?

Accepted Answer

A)  n-butane < 1-butanol < diethyl ether < 2-butanone 
B)  n-butane < 2-butanone < diethyl ether < 1-butanol 
C)  2-butanone < n-butane < diethyl ether < 1-butanol 
D)  n-butane < diethyl ether < 1-butanol < 2-butanone 
E)  n-butane < diethyl ether < 2-butanone < 1-butanol 
A)  n-butane < 1-butanol < diethyl ether < 2-butanone 
B)  n-butane < 2-butanone < diethyl ether < 1-butanol 
C)  2-butanone < n-butane < diethyl ether < 1-butanol 
D)  n-butane < diethyl ether < 1-butanol < 2-butanone 
E)  n-butane < diethyl ether < 2-butanone < 1-butanol

Question 19

Name the following compound.

Accepted Answer

5,5-difluo

Question 20

Provide the major organic product of the following reaction.

Accepted Answer

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

Exam 18: Ketones and Aldehydes

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

Another name for β-methoxybutyraldehyde is:

Provide the major organic product of the reaction shown below.

Provide the major organic product of the reaction of aniline with 3-pentanone.

Which of the following correctly describes the bond angle and hybridizations present in formaldehyde?

Name the following compound.

What compound is produced when 1,3-dithiane is subjected to the following sequence of reagents: 1. n-BuLi 2. CH3CH2Br 3. n-BuLi 4. (CH3)2CHCH2CH2I 5. HgCl2, H3O+?

In carbon NMR, the carbon atom of the carbonyl group in aldehydes and ketones has a chemical shift of about:

Would you expect the carbonyl carbon of benzaldehyde to be more or less electrophilic than that of acetaldehyde? Explain using resonance structures.

Complete the following reaction by filling in the correct reagents.

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

Provide the major organic product which results when pentanal is subjected to the following sequence of steps:

Provide the single reagent necessary for the conversion of cyclobutanone to the compound shown below.

Provide the structure of benzophenone.

Provide the structure of the semicarbazone derivative of 3-pentanone.

When HOCH2CH2CH2CH2COCH2CH2CH2CH2OH is heated in the presence of an acid catalyst, a reaction occurs. This product has the formula C9H16O2. Provide the structure of this product.

Which would be more appropriate as the reduction in the following sequence, a Clemmensen or a Wolff-Kishner? Explain.

Which of the following represents the correct ranking in terms of increasing boiling point?

Name the following compound.

Provide the major organic product of the following reaction.

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

What compound is produced when 1,3-dithiane is subjected to the following sequence of reagents: 1. n-BuLi 2. CH₃CH₂Br 3. n-BuLi 4. (CH₃)₂CHCH₂CH₂I 5. HgCl₂, H₃O⁺?

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

When HOCH₂CH₂CH₂CH₂COCH₂CH₂CH₂CH₂OH is heated in the presence of an acid catalyst, a reaction occurs. This product has the formula C₉H₁₆O₂. Provide the structure of this product.