Question 1

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 D

Question 2

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 C

Question 3

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 4

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 5

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 6

Butanal (MW= 72)has a boiling point of 76 °C while butanol (MW= 74)has a boiling point of 118 °C.What accounts for this difference in boiling points?

Accepted Answer

A) Butanol is polar while butanal is not polar. 
B) Butanol can exhibit dipole-dipole interactions while butanal cannot. 
C) Butanol can hydrogen bond and butanal cannot hydrogen bond. 
D) Butanal is less sterically hindered than butanol. 
A) Butanol is polar while butanal is not polar. 
B) Butanol can exhibit dipole-dipole interactions while butanal cannot. 
C) Butanol can hydrogen bond and butanal cannot hydrogen bond. 
D) Butanal is less sterically hindered than butanol.

Question 7

What is the product?

Accepted Answer

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

Question 8

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 9

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 10

What is the IUPAC name for the following compound?

Accepted Answer

A) Pivaldehyde 
B) 2,2-Dimethylpropanal 
C) Tert-butyl aldehyde 
D) 2,2-Dimethylpentanal 
A) Pivaldehyde 
B) 2,2-Dimethylpropanal 
C) Tert-butyl aldehyde 
D) 2,2-Dimethylpentanal

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

What compound is consistent with the following 1H NMR spectrum?

Accepted Answer

A) Acetone 
B) Propanal 
C) Cyclobutanone 
D) 2-butanone 
A) Acetone 
B) Propanal 
C) Cyclobutanone 
D) 2-butanone

Question 13

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 14

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 15

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 16

Cyclic acetals are used as protecting groups for ketones or aldehydes because they are inert to all of the following reagents except

Accepted Answer

A) aqueous acid. 
B) aqueous base. 
C) oxidizing reagents. 
D) reducing reagents. 
A) aqueous acid. 
B) aqueous base. 
C) oxidizing reagents. 
D) reducing reagents.

Question 17

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

Question 18

What is the IUPAC for the following compound?

Accepted Answer

A) 1-Formyl-2-nitropropane 
B) 1-Formyl-3-nitrobutane 
C) 2-Nitrobutanal 
D) 3-Nitrobutanal 
A) 1-Formyl-2-nitropropane 
B) 1-Formyl-3-nitrobutane 
C) 2-Nitrobutanal 
D) 3-Nitrobutanal

Question 19

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 20

Give the IUPAC name for the following compound.

Accepted Answer

A) R-3-bromobutanal 
B) S-3-bromobutanal 
C) R-2-bromobutan-4-al 
D) S-2-bromobutan-4-al 
A) R-3-bromobutanal 
B) S-3-bromobutanal 
C) R-2-bromobutan-4-al 
D) S-2-bromobutan-4-al

Exam 18: Aldehydes and Ketones - Nucleophilic Addition

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

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

What is the missing reagent in the reaction below?

What is the product of the following reaction?

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

Butanal (MW= 72)has a boiling point of 76 °C while butanol (MW= 74)has a boiling point of 118 °C.What accounts for this difference in boiling points?

What is the product?

Give the IUPAC name for the following compound.

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

What is the IUPAC name for the following compound?

What is the product of the following reaction?

What compound is consistent with the following 1H NMR spectrum?

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

Give the IUPAC name for the following compound.

What is the product of the following reaction?

Cyclic acetals are used as protecting groups for ketones or aldehydes because they are inert to all of the following reagents except

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

What is the IUPAC for the following compound?

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

Give the IUPAC name for the following compound.

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

Molecular Ion Peaks and Fragmentation Patterns

Analyzing Molecular Motion and Infrared Spectroscopy

Organic Spectroscopy Concepts

Filters

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

What compound is consistent with the following ¹H NMR spectrum?