Question 1

An ylide is a molecule that can be described as a:

Accepted Answer

A)  carbanion bound to a negatively charged heteroatom. 
B)  carbocation bound to a positively charged heteroatom. 
C)  carbocation bound to a carbon radical. 
D)  carbocation bound to a diazonium ion. 
E)  carbanion bound to a positively charged heteroatom. 
A)  carbanion bound to a negatively charged heteroatom. 
B)  carbocation bound to a positively charged heteroatom. 
C)  carbocation bound to a carbon radical. 
D)  carbocation bound to a diazonium ion. 
E)  carbanion bound to a positively charged heteroatom.

Question 2

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+ 
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+ 
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 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

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 5

Oxidation of a 2° 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 6

Acetals will react with ________.

Accepted Answer

A)  H3O⊕ 
B)  NaOCH3 
C)  PhLi 
D)  CH3CH2MgBr 
E)  NaBH4 
A)  H3O⊕ 
B)  NaOCH3 
C)  PhLi 
D)  CH3CH2MgBr 
E)  NaBH4

Question 7

Provide the major organic product which results when PhCHOHCH3 is treated with PCC.

Accepted Answer

Question 8

The double bond between carbon and oxygen is similar to an alkene C=C, except that C=O is:

Accepted Answer

A)  shorter and weaker. 
B)  shorter and stronger. 
C)  longer and weaker. 
D)  longer and stronger. 
E)  longer. 
A)  shorter and weaker. 
B)  shorter and stronger. 
C)  longer and weaker. 
D)  longer and stronger. 
E)  longer.

Question 9

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

Accepted Answer

1. HOCH₂CH₂OH, H⁺ 2. Na

Question 10

Provide the preferred reagent pair to synthesize 3-ethylpent-2-ene via a Wittig reaction.

Accepted Answer

CH₃CH₂COCH₂CH

Question 11

Treatment of a nitrile with a Grignard reagent followed by hydrolysis results in ________.

Accepted Answer

A)  an ester 
B)  a ketone 
C)  an aldehyde 
D)  an ether 
E)  an alcohol 
A)  an ester 
B)  a ketone 
C)  an aldehyde 
D)  an ether 
E)  an alcohol

Question 12

Provide a detailed, stepwise mechanism for the acid-catalyzed reaction of 2-butanone with ethylene glycol (HOCH2CH2OH) to produce an acetal.

Accepted Answer

An ylide is a molecule that can be described as a:

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

Provide the major organic product of the reaction shown below.

What product will result from the reaction shown?

Oxidation of a 2° alcohol with chromic acid results in the production of ________.

Acetals will react with ________.

Provide the major organic product which results when PhCHOHCH₃ is treated with PCC.

The double bond between carbon and oxygen is similar to an alkene C=C, except that C=O is:

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

Provide the preferred reagent pair to synthesize 3-ethylpent-2-ene via a Wittig reaction.

Treatment of a nitrile with a Grignard reagent followed by hydrolysis results in ________.

Provide a detailed, stepwise mechanism for the acid-catalyzed reaction of 2-butanone with ethylene glycol (HOCH₂CH₂OH) to produce an acetal.

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

Exam 18: Ketones and Aldehydes

An ylide is a molecule that can be described as a:

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

Provide the major organic product of the reaction shown below.

What product will result from the reaction shown?

Oxidation of a 2° alcohol with chromic acid results in the production of ________.

Acetals will react with ________.

Provide the major organic product which results when PhCHOHCH3 is treated with PCC.

The double bond between carbon and oxygen is similar to an alkene C=C, except that C=O is:

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

Provide the preferred reagent pair to synthesize 3-ethylpent-2-ene via a Wittig reaction.

Treatment of a nitrile with a Grignard reagent followed by hydrolysis results in ________.

Provide a detailed, stepwise mechanism for the acid-catalyzed reaction of 2-butanone with ethylene glycol (HOCH2CH2OH) to produce an acetal.

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 major organic product which results when PhCHOHCH₃ is treated with PCC.

Provide a detailed, stepwise mechanism for the acid-catalyzed reaction of 2-butanone with ethylene glycol (HOCH₂CH₂OH) to produce an acetal.