Question 1

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 2

What is the major product of the following reaction?

Accepted Answer

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

Question 3

Which of the following compounds is the most acidic?

Accepted Answer

A) Ethyl acetoacetate 
B) 2-Butanone 
C) 1-Butanol 
D) 3-Pentanone 
A) Ethyl acetoacetate 
B) 2-Butanone 
C) 1-Butanol 
D) 3-Pentanone

Question 4

What is the missing reagent in the reaction below?

Accepted Answer

A) Br2/AcOH 
B) I2/KOH 
C) I2 
D) KOH 
A) Br2/AcOH 
B) I2/KOH 
C) I2 
D) KOH

Question 5

Why can't you prepare 2-tert-butylcyclohexanone by the following reaction?

Accepted Answer

A) Because tert-butyl bromide is too basic. 
B) Because tert-butyl bromide cannot undergo an SN2 reaction. 
C) Because tert-butyl bromide is a nucleophile. 
D) Because tert-butyl bromide is not a stable compound. 
A) Because tert-butyl bromide is too basic. 
B) Because tert-butyl bromide cannot undergo an SN2 reaction. 
C) Because tert-butyl bromide is a nucleophile. 
D) Because tert-butyl bromide is not a stable compound.

Question 6

Which of the following is the intermediate for halogenation of ketones under acidic conditions?

Accepted Answer

A) An enolate 
B) An enol 
C) A tautomer 
D) An epimer 
A) An enolate 
B) An enol 
C) A tautomer 
D) An epimer

Question 7

Which is the more stable form of acetophenone?

Accepted Answer

A) Only I 
B) Only II 
C) Only III 
D) I and II are equally stable 
A) Only I 
B) Only II 
C) Only III 
D) I and II are equally stable

Question 8

What is the missing reagent for the following reaction?

Accepted Answer

A) Br2/HOAc 
B) Br2/KOH 
C) Cl2/FeCl3 
D) Br2/FeBr3 
A) Br2/HOAc 
B) Br2/KOH 
C) Cl2/FeCl3 
D) Br2/FeBr3

Question 9

Vitamin C is a stable enediol.Which is the structure of a possible keto form in equilibrium with the enediol form?

Accepted Answer

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

Question 10

Which of the following compounds is an enol of compound X drawn below?

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 11

Treatment of 2-hexanone with NaOCH2CH3 followed by CH3Br affords compound X (C7H14O)as the major product.X shows a strong absorption in the IR spectrum at 1713 cm-1,and its 1H NMR data is given below.What is the structure of X?

Accepted Answer

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

Question 12

Starting with cyclohexanone,how could you prepare the diketone below?

Accepted Answer

A) Treat cyclohexanone with a base under thermodynamic conditions. 
B) Hydrogenate cyclohexanone with Raney nickel. 
C) Convert cyclohexanone into the a-bromoketone and then react this with the enolate of cyclohexanone. 
D) Convert cyclohexanone into an enamine with diethylamine and then react this with more cyclohexanone. 
A) Treat cyclohexanone with a base under thermodynamic conditions. 
B) Hydrogenate cyclohexanone with Raney nickel. 
C) Convert cyclohexanone into the a-bromoketone and then react this with the enolate of cyclohexanone. 
D) Convert cyclohexanone into an enamine with diethylamine and then react this with more cyclohexanone.

Question 13

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

Accepted Answer

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

Question 14

Which of the following would undergo racemization under basic conditions?

Accepted Answer

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

Question 15

What is the starting material in the following reaction?

Accepted Answer

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

Question 16

The following molecule is called

Accepted Answer

A) a 1,3-diketopentanoate. 
B) a diethyl malonate. 
C) an ethyl acetoacetate. 
D) a b-keto ester. 
A) a 1,3-diketopentanoate. 
B) a diethyl malonate. 
C) an ethyl acetoacetate. 
D) a b-keto ester.

Question 17

Which is the most stable form of 1,3-cyclohexanedione?

Accepted Answer

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

Question 18

The malonic ester synthesis can be adapted to synthesize a-amino acids by using diethyl acetamidomalonate as the starting material.Select the structure of the amino acid produced by the following synthesis.

Accepted Answer

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

Question 19

Which is the most acidic proton in the following compound?

Accepted Answer

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

Question 20

Which of the following bases will completely convert 1,4-cyclohexandione into an enolate?

Accepted Answer

A) Sodium hydroxide 
B) Sodium methoxide 
C) Sodium tert-butoxide 
D) Sodium hydride 
A) Sodium hydroxide 
B) Sodium methoxide 
C) Sodium tert-butoxide 
D) Sodium hydride

Exam 21: Substitution Reactions of Carbonyl Compounds at the a Carbon

What is the product of the following reaction?

What is the major product of the following reaction?

Which of the following compounds is the most acidic?

What is the missing reagent in the reaction below?

Why can't you prepare 2-tert-butylcyclohexanone by the following reaction?

Which of the following is the intermediate for halogenation of ketones under acidic conditions?

Which is the more stable form of acetophenone?

What is the missing reagent for the following reaction?

Vitamin C is a stable enediol.Which is the structure of a possible keto form in equilibrium with the enediol form?

Which of the following compounds is an enol of compound X drawn below?

Treatment of 2-hexanone with NaOCH2CH3 followed by CH3Br affords compound X (C7H14O)as the major product.X shows a strong absorption in the IR spectrum at 1713 cm-1,and its 1H NMR data is given below.What is the structure of X?

Starting with cyclohexanone,how could you prepare the diketone below?

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

Which of the following would undergo racemization under basic conditions?

What is the starting material in the following reaction?

The following molecule is called

Which is the most stable form of 1,3-cyclohexanedione?

The malonic ester synthesis can be adapted to synthesize a-amino acids by using diethyl acetamidomalonate as the starting material.Select the structure of the amino acid produced by the following synthesis.

Which is the most acidic proton in the following compound?

Which of the following bases will completely convert 1,4-cyclohexandione into an enolate?

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

Aldehydes and Ketones - Nucleophilic Addition

Carboxylic Acids and the Acidity of the O-H Bond

Carboxylic Acids and Their Derivatives Nucleophilic Acyl Substitution

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

Treatment of 2-hexanone with NaOCH₂CH₃ followed by CH₃Br affords compound X (C₇H₁₄O)as the major product.X shows a strong absorption in the IR spectrum at 1713 cm^-1,and its ¹H NMR data is given below.What is the structure of X?