Question 1

What are the three steps in the malonic ester synthesis?

Accepted Answer

A) Deprotonation,alkylation,hydrolysis/decarboxylation 
B) Hydrogenation,alkylation,deprotonation 
C) Alkylation,hydrolysis/decarboxylation.hydrogenation 
D) Hydrolysis/decarboxylation,deprotonation,alkylation 
A) Deprotonation,alkylation,hydrolysis/decarboxylation 
B) Hydrogenation,alkylation,deprotonation 
C) Alkylation,hydrolysis/decarboxylation.hydrogenation 
D) Hydrolysis/decarboxylation,deprotonation,alkylation

Question 2

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 3

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 4

What is the starting material for 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 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

Question 6

Which of the following is the least acidic compound?

Accepted Answer

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

Question 7

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 8

Will acetophenone be completely deprotonated by lithium diisopropylamide (LDA)?

Accepted Answer

A) Yes 
B) No 
A) Yes 
B) No

Question 9

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 10

Which of the following four compounds is the most acidic?

Accepted Answer

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

Question 11

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 12

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 13

It has been found that b-dicarbonyl compounds have a greater concentration of the enol form over the keto form.This can be explained by

Accepted Answer

A) the C=C of the enol is conjugated with the carbonyl group. 
B) the -OH of the enol can hydrogen bond to the oxygen of the nearby carbonyl group. 
C) Both and above are true. 
D) None of the choices are true. 
A) the C=C of the enol is conjugated with the carbonyl group. 
B) the -OH of the enol can hydrogen bond to the oxygen of the nearby carbonyl group. 
C) Both and above are true. 
D) None of the choices are true.

Question 14

If you want to form a kinetic enolate,you want to

Accepted Answer

A) use a strong,non-nucleophilic base such as LDA. 
B) use a protic solvent. 
C) use a low temperature. 
D) both use a strong,non-nucleophilic base such as LDA and use a low temperature. 
A) use a strong,non-nucleophilic base such as LDA. 
B) use a protic solvent. 
C) use a low temperature. 
D) both use a strong,non-nucleophilic base such as LDA and use a low temperature.

Question 15

Why is the enolate of acetone less basic than the allyl anion derived from propene?

Accepted Answer

A) Because there are more atoms in acetone 
B) Because there are more resonance structures for the enolate of acetone 
C) It isn't; the allyl anion is less basic. 
D) One of the resonance structures for the enolate places the negative charge on the more electronegative oxygen. 
A) Because there are more atoms in acetone 
B) Because there are more resonance structures for the enolate of acetone 
C) It isn't; the allyl anion is less basic. 
D) One of the resonance structures for the enolate places the negative charge on the more electronegative oxygen.

Question 16

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 17

Which of the following compounds would undergo racemization in the presence of a base?

Accepted Answer

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

Question 18

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 19

For most compounds with a single keto group in the molecule,equilibrium favors the keto form over the enol form of the compound.This is due largely to what?

Accepted Answer

A) The C=O bond is much stronger than the C=C bond. 
B) The C=C bond is much stronger than the C=O bond. 
C) The keto form can undergo intramolecular hydrogen bonding. 
D) The enol form can undergo intramolecular hydrogen bonding. 
A) The C=O bond is much stronger than the C=C bond. 
B) The C=C bond is much stronger than the C=O bond. 
C) The keto form can undergo intramolecular hydrogen bonding. 
D) The enol form can undergo intramolecular hydrogen bonding.

Question 20

Which of the following is an enol form of the following compound?

Accepted Answer

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

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

What are the three steps in the malonic ester synthesis?

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?

The following molecule is called

What is the starting material for the following reaction?

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

Which of the following is the least acidic compound?

Which of the following compounds is the most acidic?

Will acetophenone be completely deprotonated by lithium diisopropylamide (LDA)?

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

Which of the following four compounds is the most acidic?

Which is the most acidic proton in the following compound?

What is the missing reagent for the following reaction?

It has been found that b-dicarbonyl compounds have a greater concentration of the enol form over the keto form.This can be explained by

If you want to form a kinetic enolate,you want to

Why is the enolate of acetone less basic than the allyl anion derived from propene?

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

Which of the following compounds would undergo racemization in the presence of a base?

What is the missing reagent in the reaction below?

For most compounds with a single keto group in the molecule,equilibrium favors the keto form over the enol form of the compound.This is due largely to what?

Which of the following is an enol form of 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

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

Molecular Ion Peaks and Fragmentation Patterns

Analyzing Molecular Motion and Infrared Spectroscopy

Organic Spectroscopy Concepts

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?