Question 1

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° B

Question 2

Provide the structure of cyclohexanecarbaldehyde.

Accepted Answer

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

Question 3

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

Accepted Answer

PhCH₂CH₂COCH₂CH₂CH₂CH₃

Question 4

Provide the reagents to perform the following synthesis.

Accepted Answer

1) PhLi (e

Question 5

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 6

Draw two major resonance forms of the cation which results when cyclohexanone's carbonyl group is protonated.

Accepted Answer

The answer of Draw two major resonance forms of the...

Question 7

Why are the equilibrium constants for hydration of aldehydes typically greater than those of ketones?

Accepted Answer

The carbonyl group of an aldehyde is sta

Question 8

What is the correct IUPAC name for the following compound?

Accepted Answer

A)  2-oxocyclohex-3-ene carbaldehyde 
B)  5-formylcyclohex-2-enone 
C)  2-formylcyclohex-5-enone 
D)  3-oxocyclohex-4-enal 
A)  2-oxocyclohex-3-ene carbaldehyde 
B)  5-formylcyclohex-2-enone 
C)  2-formylcyclohex-5-enone 
D)  3-oxocyclohex-4-enal

Question 9

Oxidation of a 1° alcohol with pyridinium chlorochromate 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 10

Millad NX8000, shown below, is a clarifying additive for polypropylene ( C & En News, Sept. 2010, 34). Predict the products of the following reaction.

Accepted Answer

The answer of Millad NX8000, shown below, is a clarifying...

Question 11

Name the compound generated when ethylbenzene is treated with CO, HCl, AlCl3, and CuCl.

Accepted Answer

Question 12

Provide the proper IUPAC name for (CH3)2CHCH2CH2COCH   
CH2.

Accepted Answer

6-methylhe

Question 13

What product will result from the reaction shown?

Accepted Answer

A)  acetal 
B)  hydrazine 
C)  ester 
D)  ylide 
E)  ketone 
A)  acetal 
B)  hydrazine 
C)  ester 
D)  ylide 
E)  ketone

Question 14

Provide the necessary reagents to complete the following transformation.

Accepted Answer

The answer of Provide the necessary reagents to complete the...

Question 15

Provide the structure of cyclohexanone oxime.

Accepted Answer

The answer of Provide the structure of cyclohexanone oxime....

Question 16

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 17

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 18

Propose a synthesis of 3-methylhept-4-yn-3-ol from but-1-yne.

Accepted Answer

1) NaNH₂ 2)

Question 19

Provide the structure of the major organic product which results when benzaldehyde reacts with hydroxylamine in the presence of acid.

Accepted Answer

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

Question 20

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

Exam 18: Ketones and Aldehydes

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

Provide the structure of cyclohexanecarbaldehyde.

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

Provide the reagents to perform the following synthesis.

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

Draw two major resonance forms of the cation which results when cyclohexanone's carbonyl group is protonated.

Why are the equilibrium constants for hydration of aldehydes typically greater than those of ketones?

What is the correct IUPAC name for the following compound?

Oxidation of a 1° alcohol with pyridinium chlorochromate results in the production of ________.

Millad NX8000, shown below, is a clarifying additive for polypropylene ( C & En News, Sept. 2010, 34). Predict the products of the following reaction.

Name the compound generated when ethylbenzene is treated with CO, HCl, AlCl3, and CuCl.

Provide the proper IUPAC name for (CH3)2CHCH2CH2COCH CH2.

What product will result from the reaction shown?

Provide the necessary reagents to complete the following transformation.

Provide the structure of cyclohexanone oxime.

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

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

Propose a synthesis of 3-methylhept-4-yn-3-ol from but-1-yne.

Provide the structure of the major organic product which results when benzaldehyde reacts with hydroxylamine in the presence of acid.

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

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

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

Name the compound generated when ethylbenzene is treated with CO, HCl, AlCl₃, and CuCl.

Provide the proper IUPAC name for (CH₃)₂CHCH₂CH₂COCH CH₂.