Question 1

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

Question 2

The chlorination of benzaldehyde is producing:

Accepted Answer

A)   m-chlorobenzaldehyde
B)   a mixture of o and p- chlorobenzaldehyde
C)   o -chlorobenzaldehyde
D)   p-chlorobenzaldehyde
E)   a mixture of m- and p-chlorobenzaldehydeF) A) and B)
G) B) and E)

Question 3

Which of the following are electrophiles? 
I. CH3CH2NH2 
II. CH3CH2I 
III. CH3OH

Accepted Answer

A)   I
B)   II
C)   III
D)   I + II
E)   I + IIIF) A) and C)
G) All of the above

Question 4

Organic reactions in which atoms or groups that are bonded to adjacent carbon atoms are eliminated are called elimination reactions

Accepted Answer

A) True 
 B)False

Question 5

Suggest reagents for the synthesis of meta-chloronitrobenzene from nitrobenzene.

Accepted Answer

A)   Cl2 and AlCl3
B)   HCl and AlCl3
C)   Cl2 and H2SO4
D)   HCl and HNO3
E)   Cl2 and FeBr3F) B) and D)
G) A) and C)

Question 6

What is a dehydration reaction?

Accepted Answer

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

Question 7

In which of the following reactions can alcohol participate? 
I. oxidation reactions
II. elimination reactions
III. amide synthesis
IV. peptide synthesis
V. ester synthesis

Accepted Answer

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

Question 8

Which of the following steps would you expect to occur in the addition reaction mechanism? 
I. Electrophilic attack on the unsaturated bond
II. Formation of carboanion
III. Formation of carbocation
IV. Nucleophilic attack on the carbocation
V. Elimination of a base

Accepted Answer

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

Question 9

The common general anesthetic neothyl can be produced by the following dehydration reaction. What is the systematic name of neothyl?

Accepted Answer

A)   propanone
B)   propanal
C)   methyl propanoate
D)   methyl propyl ether
E)   ethyl methyl etherF) A) and C)
G) B) and E)

Question 10

H3C∙ + ∙Cl → H3C-Cl is an example of:

Accepted Answer

A)   polymerization
B)   neutralization reaction
C)   termination step in alkane chlorination
D)   addition reaction
E)   reforming reactionF) A) and B)
G) A) and C)

Question 11

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 3BrF) All of the above
G) A) and B)

Question 12

What are the three characteristic steps in a chain-reaction polymerization?

Accepted Answer

A)   initiation, elongation and termination
B)   initiation, propagation and termination
C)   racemization, propagation and quenching
D)   propagation, formation and termination
E)   breaking, elongation and quenchingF) A) and B)
G) A) and D)

Question 13

Classify the following reaction steps as initiation, propagation or termination. A: Br-Br → 2Br∙
B: H3CH2C∙ + Br∙ → CH3CH2Br
C: 2H3CH2C∙ → CH3CH2CH2CH3

Accepted Answer

A)   Step A is initiation and steps B and C are propagation
B)   Steps A and B are initiation and step C is termination
C)   Step A is initiation, step B is termination and step C is propagation
D)   Step A is initiation, step B is propagation and step C is termination
E)   Step A is initiation and steps B and C are terminationF) All of the above
G) A) and B)

Question 14

For which type of reaction is the following an example?

Accepted Answer

A)   substitution
B)   elimination
C)   polymerization
D)   rearrangement
E)   additionF) B) and D)
G) B) and C)

Question 15

Which of the following roles can alcohols have in organic reactions?
 I. electrophile
II. solvent
III. base
IV. substrate
V. acid

Accepted Answer

A)   II, III and IV
B)   I, II, and III
C)   I, III and V
D)   II, III and V
E)   II, IV and VF) C) and D)
G) All of the above

Question 16

Which of the following groups is a meta director during electrophilic aromatic substitution?

Accepted Answer

A)   -NH2
B)   -OCH3
C)   -Br
D)   -C≡N
E)   -OCOC2H5F) None of the above
G) A) and B)

Question 17

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.F) B) and C)
G) A) and B)

Question 18

The physical properties of polymers depend on: 
I. the average molecular mass of a chain
II. the strength of intermolecular forces between the chains
III. the reaction temperature applied during synthesis
IV. the degree of crystallinity
V. the reaction pressure

Accepted Answer

A)   I) , II) , and IV) 
B)   II) , III) , and IV) 
C)   I) , II) , and V) 
D)   III) , IV) , and V) 
E)   II) , IV) , and V) F) C) and E)
G) All of the above

Question 19

You need to substitute one hydrogen with bromine on an aromatic ring. What reagents do you use?

Accepted Answer

A)   HBr and FeBr3 as catalyst
B)   Br2 and heat
C)   Br2 and FeBr3 as catalyst
D)   a mixture of HBr and conc. H2S4
E)   Br2 and radiation (hυ) F) None of the above
G) A) and E)

Question 20

Which of the following steps are a part of chain reaction during alkane substitution?
 I. Propagation
II. Initiation
III. Competition
IV. Dehalogenation
V. Termination

Accepted Answer

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

Exam 27: Reactions of Organic Compounds

Suggest reagents for the synthesis of meta-chloronitrobenzene from nitrobenzene.

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Which of the following steps would you expect to occur in the addition reaction mechanism? I. Electrophilic attack on the unsaturated bond II. Formation of carboanion III. Formation of carbocation IV. Nucleophilic attack on the carbocation V. Elimination of a base

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Organic reactions in which atoms or groups that are bonded to adjacent carbon atoms are eliminated are called elimination reactions

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Which of the following roles can alcohols have in organic reactions? I. electrophile II. solvent III. base IV. substrate V. acid

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What is a dehydration reaction?

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

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You need to substitute one hydrogen with bromine on an aromatic ring. What reagents do you use?

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Which of the following groups is a meta director during electrophilic aromatic substitution?

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The chlorination of benzaldehyde is producing:

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Classify the following reaction steps as initiation, propagation or termination. A: Br-Br → 2Br∙ B: H3CH2C∙ + Br∙ → CH3CH2Br C: 2H3CH2C∙ → CH3CH2CH2CH3

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The common general anesthetic neothyl can be produced by the following dehydration reaction. What is the systematic name of neothyl?

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The physical properties of polymers depend on: I. the average molecular mass of a chain II. the strength of intermolecular forces between the chains III. the reaction temperature applied during synthesis IV. the degree of crystallinity V. the reaction pressure

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Which of the following steps are a part of chain reaction during alkane substitution? I. Propagation II. Initiation III. Competition IV. Dehalogenation V. Termination

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Which of the following are electrophiles? I. CH3CH2NH2 II. CH3CH2I III. CH3OH

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H3C∙ + ∙Cl → H3C-Cl is an example of:

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What are the three characteristic steps in a chain-reaction polymerization?

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In which of the following reactions can alcohol participate? I. oxidation reactions II. elimination reactions III. amide synthesis IV. peptide synthesis V. ester synthesis

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

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For which type of reaction is the following an example?

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

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Classify the following reaction steps as initiation, propagation or termination. A: Br-Br → 2Br∙ B: H₃CH₂C∙ + Br∙ → CH₃CH₂Br C: 2H₃CH₂C∙ → CH₃CH₂CH₂CH₃

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Which of the following are electrophiles? I. CH₃CH₂NH₂ II. CH₃CH₂I III. CH₃OH

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H₃C∙ + ∙Cl → H₃C-Cl is an example of:

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

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Order the following substrates according to the increase in SN₂reaction rate: (CH₃) ₂CHBr, (CH₃) ₃CBr, CH₃CH₂Br, CH₃Br

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