Question 1

What sequence of reactions is required for the following transformation?

Accepted Answer

A) [1] NaOMe,[2] acetone 
B) [1] Ph3P,[2] acetone 
C) [1] Ph3P,[2] KOtBu,[3] acetone 
D) Acetone,heat 
A) [1] NaOMe,[2] acetone 
B) [1] Ph3P,[2] acetone 
C) [1] Ph3P,[2] KOtBu,[3] acetone 
D) Acetone,heat C

Question 2

What is the missing reagent in the reaction below?

Accepted Answer

A) Methanol,acid 
B) Ethanol,acid 
C) NaOEt 
D) NaOMe 
A) Methanol,acid 
B) Ethanol,acid 
C) NaOEt 
D) NaOMe B

Question 3

Is the following reaction reversible and,if so,under what conditions?

Accepted Answer

A) No 
B) Yes,under acidic conditions 
C) Yes,using Pd/C 
D) Yes,under basic conditions 
A) No 
B) Yes,under acidic conditions 
C) Yes,using Pd/C 
D) Yes,under basic conditions D

Question 4

Using 1H NMR spectroscopy,how can you tell the difference between an aldehyde and a ketone?

Accepted Answer

A) An aldehyde has a C-H stretch (one or two)between 2700-2830 cm-1. 
B) An aldehyde has a proton signal between 9-10 ppm. 
C) A ketone has signals around 2-3 ppm. 
D) A ketone has a signal around 200 ppm. 
A) An aldehyde has a C-H stretch (one or two)between 2700-2830 cm-1. 
B) An aldehyde has a proton signal between 9-10 ppm. 
C) A ketone has signals around 2-3 ppm. 
D) A ketone has a signal around 200 ppm.

Question 5

Give the IUPAC name for the following compound.

Accepted Answer

A) R-3-hydroxybutanal 
B) S-3-hydroxybutanal 
C) R-2-hydroxybutan-4-al 
D) S-2-hydroxybutan-4-al 
A) R-3-hydroxybutanal 
B) S-3-hydroxybutanal 
C) R-2-hydroxybutan-4-al 
D) S-2-hydroxybutan-4-al

Question 6

Why can't you use acidic conditions (such as aqueous hydrochloric acid)for the addition of a Grignard reagent to a ketone?

Accepted Answer

A) Because the Grignard reagent will react with the acid and be quenched 
B) Because the ketone will be protonated and thus unreactive 
C) Because the ketone will form an unreactive enol 
D) Because the Grignard reagent won't dissolve in aqueous solutions 
A) Because the Grignard reagent will react with the acid and be quenched 
B) Because the ketone will be protonated and thus unreactive 
C) Because the ketone will form an unreactive enol 
D) Because the Grignard reagent won't dissolve in aqueous solutions

Question 7

What needs to be done to make the following reaction proceed?

Accepted Answer

A) Heat the reaction. 
B) Add an acid catalyst only. 
C) Add a base catalyst only. 
D) Heat the reaction and add an acid catalyst. 
A) Heat the reaction. 
B) Add an acid catalyst only. 
C) Add a base catalyst only. 
D) Heat the reaction and add an acid catalyst.

Question 8

What is the product of the following reaction?

Accepted Answer

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

Question 9

Give the IUPAC name for the following compound.

Accepted Answer

A) R-4-hydroxy-2-pentanone 
B) S-4-hydroxy-2-pentanone 
C) R-2-hydroxy-4-pentanone 
D) S-2-hydroxy-4-pentanone 
A) R-4-hydroxy-2-pentanone 
B) S-4-hydroxy-2-pentanone 
C) R-2-hydroxy-4-pentanone 
D) S-2-hydroxy-4-pentanone

Question 10

What is the major organic product obtained from the following sequence of reactions?

Accepted Answer

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

Question 11

What is the product of the following reaction?

Accepted Answer

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

Question 12

Why are strongly acidic conditions not used in the formation of enamines and imines?

Accepted Answer

A) The carbonyl will be protonated. 
B) The amine will be completely protonated. 
C) The product is not stable to strong acid. 
D) An enol will be formed. 
A) The carbonyl will be protonated. 
B) The amine will be completely protonated. 
C) The product is not stable to strong acid. 
D) An enol will be formed.

Question 13

What is the missing reagent in the reaction below?

Accepted Answer

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

Question 14

What is the first step in nucleophilic addition under acidic conditions?

Accepted Answer

A) Protonation of the nucleophile 
B) Addition of the nucleophile 
C) Loss of water 
D) Protonation of the carbonyl 
A) Protonation of the nucleophile 
B) Addition of the nucleophile 
C) Loss of water 
D) Protonation of the carbonyl

Question 15

Which of the following oxidants would work for the following reaction?

Accepted Answer

A) H2Cr2O7 
B) FeCl3 
C) I2 
D) Ag2O 
A) H2Cr2O7 
B) FeCl3 
C) I2 
D) Ag2O

Question 16

What is the product?

Accepted Answer

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

Question 17

What is (are)the product(s)of the following reaction?

Accepted Answer

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

Question 18

Give the IUPAC name for the following compound.

Accepted Answer

A) R-4-bromo-2-pentanone 
B) S-4-bromo-2-pentanone 
C) R-2-bromo-4-pentanone 
D) S-2-bromo-4-pentanone 
A) R-4-bromo-2-pentanone 
B) S-4-bromo-2-pentanone 
C) R-2-bromo-4-pentanone 
D) S-2-bromo-4-pentanone

Question 19

What is the cyclic hemiacetal product formed from intramolecular cyclization of the following hydroxy aldehyde?

Accepted Answer

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

Question 20

What is the structure of 2-trifluoromethyl-2-methoxybutanal?

Accepted Answer

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

Exam 18: Aldehydes and Ketones - Nucleophilic Addition

What sequence of reactions is required for the following transformation?

What is the missing reagent in the reaction below?

Is the following reaction reversible and,if so,under what conditions?

Using 1H NMR spectroscopy,how can you tell the difference between an aldehyde and a ketone?

Give the IUPAC name for the following compound.

Why can't you use acidic conditions (such as aqueous hydrochloric acid)for the addition of a Grignard reagent to a ketone?

What needs to be done to make the following reaction proceed?

What is the product of the following reaction?

Give the IUPAC name for the following compound.

What is the major organic product obtained from the following sequence of reactions?

What is the product of the following reaction?

Why are strongly acidic conditions not used in the formation of enamines and imines?

What is the missing reagent in the reaction below?

What is the first step in nucleophilic addition under acidic conditions?

Which of the following oxidants would work for the following reaction?

What is the product?

What is (are)the product(s)of the following reaction?

Give the IUPAC name for the following compound.

What is the cyclic hemiacetal product formed from intramolecular cyclization of the following hydroxy aldehyde?

What is the structure of 2-trifluoromethyl-2-methoxybutanal?

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

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

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

Spectroscopy A: Mass Spectrometry

Spectroscopy B: Infrared Spectroscopy

Spectroscopy C: Nuclear Magnetic Resonance Spectroscopy

Filters

Using ¹H NMR spectroscopy,how can you tell the difference between an aldehyde and a ketone?