Question 1

Predict the product and mechanism type for the following reaction:

Accepted Answer

A)    SN2 mechanism 
B)    SN2 mechanism 
C)    SN1 mechanism 
D)    SN1 mechanism 
E)    SN1 mechanism 
A)    SN2 mechanism 
B)    SN2 mechanism 
C)    SN1 mechanism 
D)    SN1 mechanism 
E)    SN1 mechanism

Question 2

Which of the following could be added across carbon-carbon multiple bonds?
I.H2SO4
II.H2
III.H2O
IV.NO2
V.HBr

Accepted Answer

A) II,III,and V 
B) II,III,and IV 
C) I,III,and V 
D) I,III,and IV 
E) I,II,and III 
A) II,III,and V 
B) II,III,and IV 
C) I,III,and V 
D) I,III,and IV 
E) I,II,and III

Question 3

Oxidation of the following alcohol via the conditions below yields spearmint oil.What new functional group is formed in the reaction to yield spearmint?

Accepted Answer

A) aldehyde 
B) carboxylic acid 
C) ketone 
D) amine 
E) ester 
A) aldehyde 
B) carboxylic acid 
C) ketone 
D) amine 
E) ester

Question 4

Chain reaction polymerization is typical for:

Accepted Answer

A) monomers with carbon-carbon double bonds 
B) monomers with carbon oxygen double bonds 
C) monomers containing aromatic rings 
D) monomeric alkanes 
E) monomeric alcohols 
A) monomers with carbon-carbon double bonds 
B) monomers with carbon oxygen double bonds 
C) monomers containing aromatic rings 
D) monomeric alkanes 
E) monomeric alcohols

Question 5

The initiation step in chain reaction for alkene substitution produces:

Accepted Answer

A) free halogen radicals 
B) free alkyl radicals 
C) both free halogen and alkyl radicals 
D) free halonium ions 
E) free halide ions 
A) free halogen radicals 
B) free alkyl radicals 
C) both free halogen and alkyl radicals 
D) free halonium ions 
E) free halide ions

Question 6

Find the combination of conditions that are the best for SN2 reactions.

Accepted Answer

A) The substrate is a tertiary alkyl iodide,solvent is aprotic,polar and the nucleophile is a strong base. 
B) The substrate is a primary alkyl iodide,solvent is aprotic,polar and the nucleophile is a strong base. 
C) The substrate is a primary alkyl fluoride,solvent is protic,polar and the nucleophile is a strong base. 
D) The substrate is a primary alkyl iodide,solvent is non-polar and the nucleophile is a weak base. 
E) The substrate is a tertiary alkyl iodide,solvent is non-polar and the nucleophile is a strong base. 
A) The substrate is a tertiary alkyl iodide,solvent is aprotic,polar and the nucleophile is a strong base. 
B) The substrate is a primary alkyl iodide,solvent is aprotic,polar and the nucleophile is a strong base. 
C) The substrate is a primary alkyl fluoride,solvent is protic,polar and the nucleophile is a strong base. 
D) The substrate is a primary alkyl iodide,solvent is non-polar and the nucleophile is a weak base. 
E) The substrate is a tertiary alkyl iodide,solvent is non-polar and the nucleophile is a strong base.

Question 7

What product would you expect to obtain from a reaction between one isomer of 3-methyl-1-pentanol and HI?

Accepted Answer

A) a substitution product 
B) only one elimination product 
C) a substitution product with inversion of configuration 
D) two elimination products 
E) a racemic mixture of substitution products 
A) a substitution product 
B) only one elimination product 
C) a substitution product with inversion of configuration 
D) two elimination products 
E) a racemic mixture of substitution products

Question 8

Which of the following mechanistic steps do you expect in bromination of benzene with Br2 and FeBr3 as a catalyst?
I.formation of Br+[FeBr4]-
II.attack of [FeBr4]- on benzene ring
III.formation of arenium ion
IV.deprotonation of arenium ion
V.nucleophilic attack of Br+

Accepted Answer

A) I,III,and IV 
B) I,II,and IV 
C) II,III,and V 
D) III,IV,and V 
E) II,IV,and V 
A) I,III,and IV 
B) I,II,and IV 
C) II,III,and V 
D) III,IV,and V 
E) II,IV,and V

Question 9

Order the following substrates according to the increase in SN2 reaction rate:
(CH3)2CHBr, (CH3)3CBr,CH3CH2Br,CH3Br

Accepted Answer

A) (CH3)2CHBr 3)3CBr 3CH2Br 3Br 
B) (CH3)3CBr 3)2CHBr 3CH2Br 3Br 
C) (CH3)3CBr 3)2CHBr 3Br 3CH2Br 
D) (CH3)3CBr 3CH2Br 3)2CHBr 3Br 
E) CH3CH2Br 3)3CBr 3)2CHBr 3Br 
A) (CH3)2CHBr 3)3CBr 3CH2Br 3Br 
B) (CH3)3CBr 3)2CHBr 3CH2Br 3Br 
C) (CH3)3CBr 3)2CHBr 3Br 3CH2Br 
D) (CH3)3CBr 3CH2Br 3)2CHBr 3Br 
E) CH3CH2Br 3)3CBr 3)2CHBr 3Br

Question 10

Arrange the following alkenes according to their increasing stability:

Accepted Answer

A) A < B < C < D 
B) B < C < A < D 
C) B < A < C < D 
D) C < B < A < D 
E) C < A < B < D 
A) A < B < C < D 
B) B < C < A < D 
C) B < A < C < D 
D) C < B < A < D 
E) C < A < B < D

Question 11

What is the difference between atactic polymer and isotactic polymer?

Accepted Answer

A) Atactic polymer has an irregular structure while in isotactic polymer identical functional groups have the same orientation on the polymer chain. 
B) Atactic polymer has a regular zig-zag structure while in isotactic polymer identical functional groups have the same orientation on the polymer chain. 
C) Atactic polymer has the same functional groups on one side of the polymer structure while in isotactic polymer has random distribution of functional groups in its structure. 
D) Atactic polymer has an irregular structure while in isotactic polymer identical functional alternate back and forth along the polymer chain. 
E) Atactic polymer has identical functional groups alternating back and forth along the polymer chain while in isotactic polymer identical functional groups have the same orientation on the polymer chain. 
A) Atactic polymer has an irregular structure while in isotactic polymer identical functional groups have the same orientation on the polymer chain. 
B) Atactic polymer has a regular zig-zag structure while in isotactic polymer identical functional groups have the same orientation on the polymer chain. 
C) Atactic polymer has the same functional groups on one side of the polymer structure while in isotactic polymer has random distribution of functional groups in its structure. 
D) Atactic polymer has an irregular structure while in isotactic polymer identical functional alternate back and forth along the polymer chain. 
E) Atactic polymer has identical functional groups alternating back and forth along the polymer chain while in isotactic polymer identical functional groups have the same orientation on the polymer chain.

Question 12

Predict the major product for the reaction: 
CH3C≡CH + 2 HBr →

Accepted Answer

A) CH3CBr2CH3  
B) CH3CH2CHBr2  
C) CH3CHBrCH2Br 
D) CH2=CBrCH2Br 
E) no reaction 
A) CH3CBr2CH3  
B) CH3CH2CHBr2  
C) CH3CHBrCH2Br 
D) CH2=CBrCH2Br 
E) no reaction

Question 13

Arrange the following carbocations in order of decreasing stability:

Accepted Answer

A) A > B > C 
B) C > B > A 
C) B > C > A 
D) C > A > B 
E) B > A > C 
A) A > B > C 
B) C > B > A 
C) B > C > A 
D) C > A > B 
E) B > A > C

Question 14

Predict the major product for the reaction: 
2-methyl-2-butene + HBr →

Accepted Answer

A) (CH3)2CBrCH2CH3  
B) (CH3)2CBrCH=CH2  
C) (CH3)2CHCHBrCH3  
D) CH2=C(CH3)CH2CH3  
E) no reaction 
A) (CH3)2CBrCH2CH3  
B) (CH3)2CBrCH=CH2  
C) (CH3)2CHCHBrCH3  
D) CH2=C(CH3)CH2CH3  
E) no reaction

Question 15

Predict the major product for the reaction: 
2-methyl-2-pentene + HCl →

Accepted Answer

A) (CH3)2CHCHClCH2CH3  
B) CH2=C(CH3)CHClCH2CH3  
C) (CH3)2CClCCl=CHCH3  
D) (CH3)2CClCH2CH2CH3  
E) no reaction 
A) (CH3)2CHCHClCH2CH3  
B) CH2=C(CH3)CHClCH2CH3  
C) (CH3)2CClCCl=CHCH3  
D) (CH3)2CClCH2CH2CH3  
E) no reaction

Question 16

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

Accepted Answer

A) 3-chloro-5-cyanobenzaldehyde 
B) 2,6-dichloro-3-cyanobenzaldehyde 
C) 2-chloro-3-cyanobenzaldehyde 
D) 2-chloro-3-cyanobenzaldehyde and 2-chloro-5-cyanobenzaldehyde 
E) None of these 
A) 3-chloro-5-cyanobenzaldehyde 
B) 2,6-dichloro-3-cyanobenzaldehyde 
C) 2-chloro-3-cyanobenzaldehyde 
D) 2-chloro-3-cyanobenzaldehyde and 2-chloro-5-cyanobenzaldehyde 
E) None of these

Question 17

Give the product(s)of the reaction: 
CH2=CHCH3 + HCl → product(s)

Accepted Answer

A) CH3CH2CH3 + H2  
B) CH2ClCHClCH3 + H2  
C) CH3CHClCH3  
D) CH2ClCH2CH3  
E) none of these 
A) CH3CH2CH3 + H2  
B) CH2ClCHClCH3 + H2  
C) CH3CHClCH3  
D) CH2ClCH2CH3  
E) none of these

Question 18

Predict major products for the following three reactions:
I.nitration of bromobenzene
II.bromination of nitrobenzene
III.bromination of aniline (aminobenzene)

Accepted Answer

A) Reaction I.gives ortho-bromonitrobenzene 
Reaction II.gives meta-bromonitrobenzene
Reaction III.gives para-bromoaniline (para-aminobromobenzene) 
B) Reaction I.gives ortho-bromonitrobenzene and para-bromonitrobenzene 
Reaction II.gives meta-bromonitrobenzene
Reaction III.gives ortho-bromoaniline (ortho-aminobromobenzene)and para-bromoaniline (para-aminobromobenzene) 
C) Reaction I.gives meta-bromonitrobenzene 
Reaction II.gives ortho-bromonitrobenzene and para-bromonitrobenzene
Reaction III.gives ortho-bromoaniline (ortho-aminobromobenzene)and para-bromoaniline (para-aminobromobenzene) 
D) Reaction I.gives meta-bromonitrobenzene 
Reaction II.gives ortho-bromonitrobenzene and para-bromonitrobenzene
Reaction III.gives meta-bromoaniline (meta-aminobromobenzene) 
E) Reaction I.gives 1,3-bromonitrobenzene 
Reaction II.gives 1,2-bromonitrobenzene and 1,4-bromonitrobenzene
Reaction III.gives 1,2-aminobromobenzene and 1,4-aminobromobenzene 
A) Reaction I.gives ortho-bromonitrobenzene 
Reaction II.gives meta-bromonitrobenzene
Reaction III.gives para-bromoaniline (para-aminobromobenzene) 
B) Reaction I.gives ortho-bromonitrobenzene and para-bromonitrobenzene 
Reaction II.gives meta-bromonitrobenzene
Reaction III.gives ortho-bromoaniline (ortho-aminobromobenzene)and para-bromoaniline (para-aminobromobenzene) 
C) Reaction I.gives meta-bromonitrobenzene 
Reaction II.gives ortho-bromonitrobenzene and para-bromonitrobenzene
Reaction III.gives ortho-bromoaniline (ortho-aminobromobenzene)and para-bromoaniline (para-aminobromobenzene) 
D) Reaction I.gives meta-bromonitrobenzene 
Reaction II.gives ortho-bromonitrobenzene and para-bromonitrobenzene
Reaction III.gives meta-bromoaniline (meta-aminobromobenzene) 
E) Reaction I.gives 1,3-bromonitrobenzene 
Reaction II.gives 1,2-bromonitrobenzene and 1,4-bromonitrobenzene
Reaction III.gives 1,2-aminobromobenzene and 1,4-aminobromobenzene

Question 19

What is the rate law for the SN1 reactions (S is substrate and N is nucleophile)?

Accepted Answer

A) rate = k[S][N] 
B) rate = k[S] 
C) rate = k[N] 
D) rate = k[S]2 
E) rate = k[S][N]2 
A) rate = k[S][N] 
B) rate = k[S] 
C) rate = k[N] 
D) rate = k[S]2 
E) rate = k[S][N]2

Question 20

What is a dehydration reaction?

Accepted Answer

A) Dehydration is the elimination of water molecule from an alcohol molecule to produce alkene. 
B) A dehydration reaction is the removal of one equivalent of H2 from an alkane to produce alkene. 
C) A dehydration reaction is one of the steps in chain-reaction polymerization. 
D) A dehydration reaction is the removal of crystalline water. 
E) A dehydration reaction is the deprotonation of a substrate with a strong base in E2 mechanism. 
A) Dehydration is the elimination of water molecule from an alcohol molecule to produce alkene. 
B) A dehydration reaction is the removal of one equivalent of H2 from an alkane to produce alkene. 
C) A dehydration reaction is one of the steps in chain-reaction polymerization. 
D) A dehydration reaction is the removal of crystalline water. 
E) A dehydration reaction is the deprotonation of a substrate with a strong base in E2 mechanism.

Exam 27: Reactions of Organic Compounds

Predict the product and mechanism type for the following reaction:

Which of the following could be added across carbon-carbon multiple bonds? I.H2SO4 II.H2 III.H2O IV.NO2 V.HBr

Oxidation of the following alcohol via the conditions below yields spearmint oil.What new functional group is formed in the reaction to yield spearmint?

Chain reaction polymerization is typical for:

The initiation step in chain reaction for alkene substitution produces:

Find the combination of conditions that are the best for SN2 reactions.

What product would you expect to obtain from a reaction between one isomer of 3-methyl-1-pentanol and HI?

Which of the following mechanistic steps do you expect in bromination of benzene with Br2 and FeBr3 as a catalyst? I.formation of Br+[FeBr4]- II.attack of [FeBr4]- on benzene ring III.formation of arenium ion IV.deprotonation of arenium ion V.nucleophilic attack of Br+

Order the following substrates according to the increase in SN2 reaction rate: (CH3)2CHBr, (CH3)3CBr,CH3CH2Br,CH3Br

Arrange the following alkenes according to their increasing stability:

What is the difference between atactic polymer and isotactic polymer?

Predict the major product for the reaction: CH3C≡CH + 2 HBr →

Arrange the following carbocations in order of decreasing stability:

Predict the major product for the reaction: 2-methyl-2-butene + HBr →

Predict the major product for the reaction: 2-methyl-2-pentene + HCl →

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

Give the product(s)of the reaction: CH2=CHCH3 + HCl → product(s)

Predict major products for the following three reactions: I.nitration of bromobenzene II.bromination of nitrobenzene III.bromination of aniline (aminobenzene)

What is the rate law for the SN1 reactions (S is substrate and N is nucleophile)?

What is a dehydration reaction?

Matter: Its Properties and Measurement

Atoms and the Atomic Theory

Chemical Compounds

Chemical Reactions

Introduction to Reactions in Aqueous Solutions

Gases

Thermochemistry

Electrons in Atoms

The Periodic Table and Some Atomic Properties

Chemical Bonding I: Basic Concepts

Chemical Bonding Ii: Valence Bond and Molecular Orbital Theories

Intermolecular Forces: Liquids and Solids

Spontaneous Change: Entropy and Gibbs Energy

Solutions and Their Physical Properties

Principles of Chemical Equilibrium

Acids and Bases

Additional Aspects of Acidbase Equilibria

Solubility and Complex-Ion Equilibria

Electrochemistry

Chemical Kinetics

Chemistry of the Main-Group Elements I: Groups 1,2,13,and 14

Chemistry of the Main-Group Elements Ii: Groups 18,17,16,15,and Hydrogen

The Transition Elements

Complex Ions and Coordination Compounds

Nuclear Chemistry

Structures of Organic Compounds

Chemistry of the Living State

Filters

Which of the following could be added across carbon-carbon multiple bonds? I.H₂SO₄ II.H₂ III.H₂O IV.NO₂ V.HBr

Find the combination of conditions that are the best for S_N2 reactions.

Which of the following mechanistic steps do you expect in bromination of benzene with Br₂ and FeBr₃ as a catalyst? I.formation of Br⁺[FeBr₄]^- II.attack of [FeBr₄]^- on benzene ring III.formation of arenium ion IV.deprotonation of arenium ion V.nucleophilic attack of Br⁺

Order the following substrates according to the increase in S_N2 reaction rate: (CH₃)₂CHBr, (CH₃)₃CBr,CH₃CH₂Br,CH₃Br

Predict the major product for the reaction: CH₃C≡CH + 2 HBr →

Give the product(s)of the reaction: CH₂=CHCH₃ + HCl → product(s)

What is the rate law for the S_N1 reactions (S is substrate and N is nucleophile)?