Question 1

What needs to be done to make the following reaction go to starting materials?

Accepted Answer

A) Heat the reaction. 
B) Add aqueous acid. 
C) Add aqueous base. 
D) Add water. 
A) Heat the reaction. 
B) Add aqueous acid. 
C) Add aqueous base. 
D) Add water.

Question 2

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 3

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 4

Which of the following products is (are)formed by Wittig reaction of CH3CH2CH2CHO with Ph3P CHCH3?

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 5

What product is formed when the following compound is hydrolyzed with aqueous acid?

Accepted Answer

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

Question 6

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 7

Which of the following will have the highest wave number for the carbonyl stretch in the IR spectrum?

Accepted Answer

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

Question 8

What is the missing reagent in the reaction below?

Accepted Answer

A) Ethyl amine,mild acid 
B) Diethylamine,mild acid 
C) Diethylamine,strong acid 
D) Diethylamine,NaOMe 
A) Ethyl amine,mild acid 
B) Diethylamine,mild acid 
C) Diethylamine,strong acid 
D) Diethylamine,NaOMe

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 product of the following reaction?

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

What is the product of the following sequence of reactions?

Accepted Answer

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

Question 13

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 14

Which of the following statements about carbohydrates is not true?

Accepted Answer

A) Carbohydrates are sugars and starches. 
B) Carbohydrates often contain acetals and hemiacetals. 
C) In solution,glucose is in the cyclic acetal form only. 
D) Glucose can form a cyclic hemiacetal from the acyclic polyhydroxy aldehyde. 
A) Carbohydrates are sugars and starches. 
B) Carbohydrates often contain acetals and hemiacetals. 
C) In solution,glucose is in the cyclic acetal form only. 
D) Glucose can form a cyclic hemiacetal from the acyclic polyhydroxy aldehyde.

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

How would the following compounds be distinguishable using IR and 1H NMR spectroscopy?

Accepted Answer

A) The 1H NMR spectrum of compound I will have two singlets. 
B) The C=O absorption in the IR spectrum of compound I will be at a higher wave number than that of compound II. 
C) The 1H NMR spectrum of compound II will have one triplet at a chemical shift of about 4. 
D) The 1H NMR spectrum of compound I will have two singlets AND the C=O absorption in the IR spectrum of compound I will be at a higher wave number than that of compound II. 
A) The 1H NMR spectrum of compound I will have two singlets. 
B) The C=O absorption in the IR spectrum of compound I will be at a higher wave number than that of compound II. 
C) The 1H NMR spectrum of compound II will have one triplet at a chemical shift of about 4. 
D) The 1H NMR spectrum of compound I will have two singlets AND the C=O absorption in the IR spectrum of compound I will be at a higher wave number than that of compound II.

Question 17

Identify how you could synthesize an enamine.

Accepted Answer

A) React a ketone or an aldehyde with a secondary amine. 
B) React a ketone or an aldehyde with a primary amine. 
C) React a ylide with a primary amine. 
D) React a ylide with a secondary amine. 
A) React a ketone or an aldehyde with a secondary amine. 
B) React a ketone or an aldehyde with a primary amine. 
C) React a ylide with a primary amine. 
D) React a ylide with a secondary amine.

Question 18

Name the following aldehyde.

Accepted Answer

A) 1-Methylcyclopentanal 
B) 2-Methylcyclopentanal 
C) 2-Methylcyclopentanecarbaldehyde 
D) 1-Methylcyclopentanylcarbaldehyde 
A) 1-Methylcyclopentanal 
B) 2-Methylcyclopentanal 
C) 2-Methylcyclopentanecarbaldehyde 
D) 1-Methylcyclopentanylcarbaldehyde

Question 19

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

Accepted Answer

A) A ketone has no carbonyl stretch at 1720 cm-1. 
B) An aldehyde has a carbonyl stretch at 1820 cm-1. 
C) An aldehyde has two C-H stretches between 2700-2850 cm-1. 
D) A ketone has no C-H stretches. 
A) A ketone has no carbonyl stretch at 1720 cm-1. 
B) An aldehyde has a carbonyl stretch at 1820 cm-1. 
C) An aldehyde has two C-H stretches between 2700-2850 cm-1. 
D) A ketone has no C-H stretches.

Question 20

Which is the most reactive carbonyl compound?

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 needs to be done to make the following reaction go to starting materials?

What is the IUPAC name for the following compound?

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?

Which of the following products is (are)formed by Wittig reaction of CH3CH2CH2CHO with Ph3P CHCH3?

What product is formed when the following compound is hydrolyzed with aqueous acid?

What is the product of the following reaction?

Which of the following will have the highest wave number for the carbonyl stretch in the IR spectrum?

What is the missing reagent in the reaction below?

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

What is the product of the following reaction?

What is the product of the following reaction?

What is the product of the following sequence of reactions?

What is the product of the following reaction?

Which of the following statements about carbohydrates is not true?

What is the product of the following reaction?

How would the following compounds be distinguishable using IR and 1H NMR spectroscopy?

Identify how you could synthesize an enamine.

Name the following aldehyde.

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

Which is the most reactive carbonyl 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

Spectroscopy A: Mass Spectrometry

Spectroscopy B: Infrared Spectroscopy

Spectroscopy C: Nuclear Magnetic Resonance Spectroscopy

Filters

Which of the following products is (are)formed by Wittig reaction of CH₃CH₂CH₂CHO with Ph₃P CHCH₃?

How would the following compounds be distinguishable using IR and ¹H NMR spectroscopy?