Question 1

What is the missing reagent in the reaction below?

Accepted Answer

A) [1] LiAlH4,[2] H2O 
B) [1] CH3MgBr (excess),[2] H2O 
C) [1] (CH3)2CuLi (excess),[2] H2O 
D) [1] DIBAL-H,[2] H2O 
A) [1] LiAlH4,[2] H2O 
B) [1] CH3MgBr (excess),[2] H2O 
C) [1] (CH3)2CuLi (excess),[2] H2O 
D) [1] DIBAL-H,[2] H2O

Question 2

Rank the carbon-metal bond in the following organometallic reagents in order of decreasing polarity,starting with the most polar.

Accepted Answer

A) II > I > III 
B) II > III > I 
C) III > I > II 
D) III > II > I 
A) II > I > III 
B) II > III > I 
C) III > I > II 
D) III > II > I

Question 3

Why would the alcohol in the following compound need to be protected before reaction?

Accepted Answer

A) If it isn't protected,the product will be a carboxylic acid. 
B) The Grignard reagent will react with the alcohol before the ketone. 
C) Magnesium is Lewis acidic and will coordinate with the alcohol. 
D) There is no need to protect the alcohol. 
A) If it isn't protected,the product will be a carboxylic acid. 
B) The Grignard reagent will react with the alcohol before the ketone. 
C) Magnesium is Lewis acidic and will coordinate with the alcohol. 
D) There is no need to protect the alcohol.

Question 4

What is the major organic product of the following reaction?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Question 5

Which of the following statements about organometallic reagents is not true?

Accepted Answer

A) Organometallic reagents contain a carbon atom bonded to a metal. 
B) The more polar the carbon-metal bond,the more reactive the organometallic reagent. 
C) Organometallic reagents react as bases and nucleophiles. 
D) Organometallic reagents are strong acids that readily donate a proton to water. 
A) Organometallic reagents contain a carbon atom bonded to a metal. 
B) The more polar the carbon-metal bond,the more reactive the organometallic reagent. 
C) Organometallic reagents react as bases and nucleophiles. 
D) Organometallic reagents are strong acids that readily donate a proton to water.

Question 6

What is the major organic product of the following reaction?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Question 7

What is the major product from the following reaction?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Question 8

If a compound is reduced,what is the result?

Accepted Answer

A) Fewer C-H bonds 
B) Increased number of C-H bonds 
C) Fewer C-Z bonds 
D) Both increased number of C-H bonds and fewer C-Z bonds 
A) Fewer C-H bonds 
B) Increased number of C-H bonds 
C) Fewer C-Z bonds 
D) Both increased number of C-H bonds and fewer C-Z bonds

Question 9

What is the major organic product of the following reaction?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Question 10

The behavior of acid chlorides is different from that of aldehydes in a reaction with a nucleophile because

Accepted Answer

A) the acid chloride contains a better leaving group 
B) the aldehyde is more easily oxidized 
C) the carbonyl of the aldehyde is more positive 
D) the carbonyl of the aldehyde is less hindered 
A) the acid chloride contains a better leaving group 
B) the aldehyde is more easily oxidized 
C) the carbonyl of the aldehyde is more positive 
D) the carbonyl of the aldehyde is less hindered

Question 11

What is the name of the general reaction type that carboxylic acids,esters,and amides undergo?

Accepted Answer

A) Electrophilic acyl addition 
B) Nucleophilic acyl addition 
C) Nucleophilic acyl substitution 
D) Electrophilic acyl substitution 
A) Electrophilic acyl addition 
B) Nucleophilic acyl addition 
C) Nucleophilic acyl substitution 
D) Electrophilic acyl substitution

Question 12

Rank the following compounds in order of increasing reactivity (least to most reactive)with respect to acyl substitution. I.methyl benzoate
II)benzoylchloride
III)benzamide

Accepted Answer

A) III< I < II 
B) II < I < III 
C) II < III < I 
D) I < III < II 
A) III< I < II 
B) II < I < III 
C) II < III < I 
D) I < III < II

Question 13

What is the name of the general reaction type that aldehydes and ketones undergo?

Accepted Answer

A) Electrophilic addition 
B) Nucleophilic addition 
C) Nucleophilic substitution 
D) Electrophilic substitution 
A) Electrophilic addition 
B) Nucleophilic addition 
C) Nucleophilic substitution 
D) Electrophilic substitution

Question 14

If the starting material has no stereogenic centers,when carbonyl compounds are reduced with a reagent such as LiAlH4 or NaBH4 and a new stereogenic center is formed,what will the composition of the product mixture be?

Accepted Answer

A) Forms a racemic mixture of the two possible enantiomers 
B) Forms more of one enantiomer than another because of steric reactions around the carbonyl 
C) Forms more of one enantiomer than another depending on the temperature of the reaction 
D) Forms different products depending on the solvent used 
A) Forms a racemic mixture of the two possible enantiomers 
B) Forms more of one enantiomer than another because of steric reactions around the carbonyl 
C) Forms more of one enantiomer than another depending on the temperature of the reaction 
D) Forms different products depending on the solvent used

Question 15

What is the missing reagent in the reaction below?

Accepted Answer

A) Et2CuLi then H2O 
B) EtMgBr then H2O 
C) NaBH4/CH3OH 
D) H2,Pd-C 
A) Et2CuLi then H2O 
B) EtMgBr then H2O 
C) NaBH4/CH3OH 
D) H2,Pd-C

Question 16

What will be the product of the following reaction (before any aqueous work-up)?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Question 17

What is the missing reagent in the reaction below?

Accepted Answer

A) [1] LiAlH4,[2] H2O 
B) [1] CH2=CHLi,[2] H2O 
C) [1] (CH2=CH)2CuLi,[2] H2O 
D) [1] DIBAL-H,[2] H2O 
A) [1] LiAlH4,[2] H2O 
B) [1] CH2=CHLi,[2] H2O 
C) [1] (CH2=CH)2CuLi,[2] H2O 
D) [1] DIBAL-H,[2] H2O

Question 18

What is the product of the following reaction?

Accepted Answer

A) Only I 
B) Only II 
C) Only III 
D) Only I and II 
A) Only I 
B) Only II 
C) Only III 
D) Only I and II

Question 19

What carbonyl compound and Grignard reagent could be used to prepare 2-butanol?

Accepted Answer

A) Only I 
B) Only II 
C) Only III 
D) Only I and II 
A) Only I 
B) Only II 
C) Only III 
D) Only I and II

Exam 17: Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

What is the missing reagent in the reaction below?

Rank the carbon-metal bond in the following organometallic reagents in order of decreasing polarity,starting with the most polar.

Why would the alcohol in the following compound need to be protected before reaction?

What is the major organic product of the following reaction?

Which of the following statements about organometallic reagents is not true?

What is the major organic product of the following reaction?

What is the major product from the following reaction?

If a compound is reduced,what is the result?

What is the major organic product of the following reaction?

The behavior of acid chlorides is different from that of aldehydes in a reaction with a nucleophile because

What is the name of the general reaction type that carboxylic acids,esters,and amides undergo?

Rank the following compounds in order of increasing reactivity (least to most reactive)with respect to acyl substitution. I.methyl benzoate II)benzoylchloride III)benzamide

What is the name of the general reaction type that aldehydes and ketones undergo?

If the starting material has no stereogenic centers,when carbonyl compounds are reduced with a reagent such as LiAlH4 or NaBH4 and a new stereogenic center is formed,what will the composition of the product mixture be?

What is the missing reagent in the reaction below?

What will be the product of the following reaction (before any aqueous work-up)?

What is the missing reagent in the reaction below?

What is the product of the following reaction?

What carbonyl compound and Grignard reagent could be used to prepare 2-butanol?

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alkyl Halides and Elimination Reactions

Alcohols,ethers,and Related Compounds

Alkenes and Addition Reactions

Alkynes and Synthesis

Oxidation and Reduction

Radical Reactions

Conjugation, resonance, and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones - Nucleophilic Addition

Carboxylic Acids and the Acidity of the O-H Bond

Carboxylic Acids and Their Derivatives - Nucleophilic Acyl Substitution

Substitution Reactions of Carbonyl Compounds at the a Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond-Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Synthetic Polymers

Lipids

Molecular Ion Peaks and Fragmentation Patterns

Analyzing Molecular Motion and Infrared Spectroscopy

Organic Spectroscopy Concepts

Filters

If the starting material has no stereogenic centers,when carbonyl compounds are reduced with a reagent such as LiAlH₄ or NaBH₄ and a new stereogenic center is formed,what will the composition of the product mixture be?