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Organic Chemistry 2nd Edition Klein Test Bank

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Organic Chemistry 2nd Edition Klein Test Bank

ISBN:

1118452283

ISBN-13:

9781118452288

 

Description

Organic Chemistry 2nd Edition Klein Test Bank

ISBN:

1118452283

ISBN-13:

9781118452288

 

 

 

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Chapter 11 Testbank

Klein

 

Chapter 11

Topic:  Radicals

Section:  11.1

Difficulty Level:  Easy

 

  1. Which of the following are the products of a homolytic cleavage of a C-C bond of ethane?

 

Ans:  A

 

Chapter 11

Topic:  Radicals

Section:  11.1

Difficulty Level:  Easy

 

  1. Which of the following is the most stable radical?

 

Ans:  B

 

Chapter 11

Topic:  Radicals

Section:  11.1

Difficulty Level:  Easy

 

  1. In the molecule shown below, determine which of the highlighted C-H bonds (from a to e) is expected to have the lowest bond dissociation energy.
  2. A) C-Ha
  3. B) C-Hb
  4. C) C-Hc
  5. D) C-Hd
  6. E) C-He

 

Ans:  C

 

Chapter 11

Topic:  Radicals

Section:  11.1

Difficulty Level:  Easy

 

  1. Use correct arrow formalism to show a homolytic bond cleavage of ethane to produce two methyl radicals.

 

Ans:

 

Chapter 11

Topic:  Radicals

Section:  11.1

Difficulty Level:  Medium

 

  1. Rank the following radicals in order of decreasing stability (most stable to least stable).

 

  1. A) IV > I > II > III
  2. B) III > I > II > IV
  3. C) III > II > I > IV
  4. D) III > IV > II > I
  5. E) II > III > I > IV

 

Ans:  C

 

 

Chapter 11

Topic:  Radicals

Section:  11.1

Difficulty Level:  Difficult

 

  1. Rank the following radicals in order of decreasing stability (most stable to least stable).

 

  1. A) IV > I > II > III
  2. B) III > I > II > IV
  3. C) III > II > I > IV
  4. D) III > IV > II > I
  5. E) II > I > III > IV

 

Ans:  E

 

 

 

Chapter 11

Topic:  Radicals

Section:  11.1

Difficulty Level:  Medium

 

  1. Using correct arrow formalism, draw all of the reasonable resonance structures for the radical shown below.

 

 

Ans:

 

Chapter 11

Topic:  Radicals

Section:  11.1

Difficulty Level:  Medium

 

 

  1. Use correct arrow formalism to draw all of the reasonable resonance structures for the radical shown below.

 

 

Ans:

 

 

Chapter 11

Topic:  Radicals

Section:  11.1

Difficulty Level:  Medium

 

  1. Which of the labeled C-H bonds is the weakest?

 

 

  1. A) C-Ha
  2. B) C-Hb
  3. C) C-Hc
  4. D) C-Hd
  5. E) C-He

 

Ans:  D

 

 

 

Chapter 11

Topic:  Common Patterns in Radical Mechanisms

Section:  11.2

Difficulty Level:  Medium

 

  1. Which term most accurately describes the process shown below?

 

 

  1. coupling
  2. proton transfer
  3. halogen abstraction
  4. hydrogen abstraction
  5. homolytic cleavage

 

Ans:  D

 

Chapter 11

Topic:  Common Patterns in Radical Mechanisms

Section:  11.2

Difficulty Level:  Easy

 

  1. Use correct arrow formalism to show the mechanism of the following radical process:

 

 

Ans:

 

Chapter 11

Topic:  Common Patterns in Radical Mechanisms

Section:  11.2

Difficulty Level:  Easy

 

  1. Which term most accurately describes the process shown below?

 

 

  1. A) hydrogen abstraction
  2. B) halogen abstraction
  3. C) homolytic cleavage
  4. D) coupling
  5. E) elimination

Ans:  D

 

Chapter 11

Topic:  Common Patterns in Radical Mechanisms

Section:  11.2

Difficulty Level:  Easy

 

  1. Use correct arrow formalism to show the mechanism of the following radical process:

 

 

Ans:

 

 

Chapter 11

Topic:  Common Patterns in Radical Mechanisms

Section:  11.2

Difficulty Level:  Easy

 

  1. Which term most accurately describes the process shown below?

 

  1. A) coupling
  2. B) hydrogen abstraction
  3. C) halogen abstraction
  4. D) homolytic cleavage
  5. E) addition to a p bond

 

Ans:  E

 

Chapter 11

Topic:  Common Patterns in Radical Mechanisms

Section:  11.2

Difficulty Level:  Easy

 

  1. Use correct arrow formalism to show the mechanism of the following radical process:

 

 

Ans:

 

 

Chapter 11

Topic:  Common Patterns in Radical Mechanisms

Section:  11.2

Difficulty Level:  Easy

 

  1. Which term most accurately describes the process shown below?

 

 

  1. A) coupling
  2. B) elimination
  3. C) halogen abstraction
  4. D) hydrogen abstraction
  5. E) homolytic cleavage

 

Ans:  B

 

 

Chapter 11

Topic:  Common Patterns in Radical Mechanisms

Section:  11.2

Difficulty Level:  Easy

 

  1. Use correct arrow formalism consistent with the following radical process:

 

 

Ans:

 

Chapter 11

Topic:  Common Patterns in Radical Mechanisms

Section:  11.2

Difficulty Level:  Easy

 

  1. Which of the following is an example of termination?

 

 

Ans:  C

 

Chapter 11

Topic:  Common Patterns in Radical Mechanisms

Section:  11.2

Difficulty Level:  Easy

 

  1. Which of the following is an example of initiation?

 

 

Ans:  B

 

Chapter 11

Topic:  Common Patterns in Radical Mechanisms

Section:  11.2

Difficulty Level:  Medium

 

  1. A bromine radical can add to the p bond of 2-methylpropene.  Use correct arrow formalism to show this process and the expected result.

 

Ans:

 

Br adds to the least substituted end of the double bond because the resulting radical (3˚) is more stable than the alternative (1˚ if Br adds to the central C).

 

 

Chapter 11

Topic:  Chlorination of Methane

Section:  11.3

Difficulty Level:  Medium

 

  1. Which of the following represents a propagation step in the monochlorination of methylene chloride (CH2Cl2)?

 

 

Ans:  B

 

Chapter 11

Topic:  Chlorination of Methane

Section:  11.3

Difficulty Level:  Medium

 

  1. Which of the following would you expect to function as an initiator at the lowest temperature?

 

 

Ans:  D

 

 

Chapter 11

Topic:  Chlorination of Methane

Section:  11.3

Difficulty Level:  Medium

 

  1. Use correct arrow formalism to show the propagation steps in the chlorination of propane to produce 2-chloropropane.

 

Ans:

 

 

Chapter 11

Topic:  Chlorination of Methane

Section:  11.3

Difficulty Level:  Medium

 

  1. Which of the following are possible termination steps in the chlorination of methane?

 

Ans:  C and D

 

 

Chapter 11

Topic:  Chlorination of Methane

Section:  11.3

Difficulty Level:  Medium

 

  1. Which of the following is most reactive towards chlorination?

 

  1. A) methane
  2. B) chloromethane
  3. C) dichloromethane
  4. D) chloroform
  5. E) ethane

 

Ans:  D

 

Chapter 11

Topic:  Chlorination of Methane

Section:  11.3

Difficulty Level:  Easy

 

  1. Free radical chlorination of ethane can produce higher halogenation products (dichlorinated, trichlorinated, etc…) in addition to chloroethane. How could the production of higher halogenated products be minimized?

 

  1. A) Use an excess of chlorine
  2. B) Use an excess of ethane
  3. C) Use equimolar chlorine and ethane
  4. D) It is not possible to minimize the production of higher halogenated products

 

Ans:  B

 

Chapter 11

Topic:  Chlorination of Methane

Section:  11.3

Difficulty Level:  Easy

 

  1. Which of the following shows the initiation step of monochlorination of methane?

 

 

  1. I
  2. II
  3. III
  4. IV
  5. I and II

 

Ans:  A

 

Chapter 11

Topic:  Chlorination of Methane

Section:  11.3

Difficulty Level:  Easy

 

  1. How many constitutional isomers are possible if propane is dichlorinated? Draw them.

 

Ans:  4

 

Chapter 11

Topic:  Thermodynamic Considerations for Halogenation Reactions

Section:  11.4

Difficulty Level:  Easy

 

  1. Which of the following processes is responsible for the fact that free radical bromination of methane is slower than free radical chlorination?

 

  1. initiation
  2. hydrogen abstraction
  3. halogen abstraction
  4. termination
  5. entropy

 

Ans:  B

 

Topic:  Thermodynamic Considerations for Halogenation Reactions

Section:  11.4

Difficulty Level:  Easy

 

  1. Which of the following is the rate-determining step in the free-radical bromination of methane?

 

 

 

Ans:  B

 

 

Chapter 11

Topic:  Regioselectivity of Halogenation

Section:  11.5

Difficulty Level:  Medium

 

  1. Predict the major product obtained upon radical bromination of t-butylcyclohexane.

 

  1. A) 1-bromo-1-tert-butylcyclohexane
  2. B) 2-bromo-1-tert-butylcyclohexane
  3. C) 3-bromo-1-tert-butylcyclohexane
  4. D) 4-bromo-1-tert-butylcyclohexane
  5. E) (1-bromo-1,1-dimethyl)ethylcyclohexane

 

Ans:  A

 

Chapter 11

Topic:  Regioselectivity of Halogenation

Section:  11.5

Difficulty Level:  Hard

 

  1. Cyclic compound A has molecular formula C5H10 and undergoes monochlorination to yield exactly three different constitutional isomers.  Identify compound A and show the monochlorination products.

 

Ans:

 

Chapter 11

Topic:  Regioselectivity of Halogenation

Section:  11.5

Difficulty Level:  Easy

 

  1. Predict the major product of the following reaction:

Ans: D

 

 

Chapter 11

Topic:  Regioselectivity of Halogenation

Section:  11.5

Difficulty Level:  Easy

 

  1. Predict the major product(s) of the following reaction:

 

Ans:  A and B

 

Chapter 11

Topic:  Regioselectivity of Halogenation

Section:  11.5

Difficulty Level:  Easy

 

  1. Both compounds A and B have molecular formula C6H14.  Monochlorination of  compound A results in formation of two constitutional isomers.  Monochlorination of compound B results in formation of four constitutional isomers.  Identify compounds A and B, and show the products of each monochlorination.

 

Ans:

 

Chapter 11

Topic:  Regioselectivity of Halogenation

Section:  11.5

Difficulty Level:  Easy

 

  1. Which of the following correctly describes the nature of the transition state of the rate-determining step of the free-radical bromination of methane?

 

  1. the transition state resembles the reactants more than the products
  2. the transition state resembles the products more than the reactants
  3. the transition state equally resembles products and reactants

 

Ans:  B

 

Chapter 11

Topic:  Stereochemistry of Halogenation

Section:  11.6

Difficulty Level:  Easy

 

  1. Predict the major product(s) of the following reaction.

 

Ans:

 

 

Chapter 11

Topic:  Stereochemistry of Halogenation

Section:  11.6

Difficulty Level:  Easy

 

  1. Which of the following is the correct name for the major product of the following reaction?

 

 

 

  1. (R)-3-bromo-3-ethylbutane
  2. (S)-3-bromo-3-ethylbutane
  3. (R)-3-bromo-3-methylpentane
  4. (S)-3-bromo-3-methylpentane
  5. 3-bromo-3-methylpentane

 

Ans:  E

 

 

 

Chapter 11

Topic:  Stereochemistry of Halogenation

Section:  11.6

Difficulty Level:  Easy

 

  1. Predict the major product(s) of the following reaction.

Ans:

 

 

Chapter 11

Topic:  Stereochemistry of Halogenation

Section:  11.6

Difficulty Level:  Easy

 

  1. Predict the major product(s) of the following reaction.

 

 

  1. I
  2. II and IV
  3. III and V
  4. I and IV
  5. V

 

Ans:  D

 

Chapter 11

Topic:  Stereochemistry of Halogenation

Section:  11.6

Difficulty Level:  Difficult

 

  1. Predict the major product(s) of the following reaction.
  2. I
  3. I and II
  4. I, II, and III
  5. I, II, III
  6. IV

 

Ans:  B

 

Chapter 11

Topic:  Stereochemistry of Halogenation

Section:  11.6

Difficulty Level:  Easy

 

  1. Compound A has molecular formula C9H20.  Compound A produces exactly three constitutional isomers upon monochlorination, and one major constitutional isomer upon monobromination.  Which of the following are possible structures of compound A?

 

 

Ans:  V

 

Chapter 11

Topic:  Stereochemistry of Halogenation

Section:  11.6

Difficulty Level:  Difficult

 

  1. Which of the following are possible product(s) of the reaction shown?

 

 

  1. I
  2. I, II
  3. I, II, IV, V
  4. I, III, IV, V
  5. I, II, III, IV, IV

 

Ans:  D

 

Chapter 11

Topic:  Stereochemistry of Halogenation

Section:  11.6

Difficulty Level:  Medium

 

  1. Draw the major product(s) of the following reaction.  Is the product optically active?  Explain.

 

Ans:    The product is not optically active.  It has no chirality centers.

 

 

 

Chapter 11

Topic:  Stereochemistry of Halogenation

Section:  11.6

Difficulty Level:  Medium

 

  1. Draw the major product(s) of the following reaction.  Is the product optically active?  Explain.

Ans:

The product is not optically active.  Equal amounts of the two enantiomers are produced.

 

 

Chapter 11

Topic:  Stereochemistry of Halogenation

Section:  11.6

Difficulty Level:  Medium

 

  1. Draw all possible monochlorination products of 3,3-dimethylpentane, including stereoisomers.

 

 

 

Chapter 11

Topic:  Allylic Bromination

Section:  11.7

Difficulty Level:  Medium

 

  1. Which of the following is (are) the likely major product(s) of the reaction shown?

 

 

  1. I
  2. II
  3. III
  4. I and III
  5. I and IV

 

Ans:  E

 

Chapter 11

Topic:  Allylic Bromination

Section:  11.7

Difficulty Level:  Easy

 

  1. What reagents would best accomplish the following transformation?

 

 

  1. Br2
  2. PBr3
  3. CH3Br
  4. NBS, heat

 

 

Ans:  D

 

Chapter 11

Topic:  Allylic Bromination

Section:  11.7

Difficulty Level:  Easy

 

  1. Which of the following are major products of the reaction shown?

 

 

  1. I
  2. I, II
  3. I, IV
  4. I, III
  5. I, II, III, IV

 

Ans:  E

 

Chapter 11

Topic:  Allylic Bromination

Section:  11.7

Difficulty Level:  Medium

 

  1. Compound A has molecular formula C6H12.  Upon treatment with NBS and irradiation with UV light, exactly two compounds (including stereoisomers) are formed.  Suggest a possible structure for compound A.

 

 

 

Chapter 11

Topic:  Allylic Bromination

Section:  11.7

Difficulty Level:  Difficult

 

  1. Upon treatment of 1-methylcyclopentene with NBS and irradiation with UV light, exactly nine compounds (including stereoisomers) are formed.  Draw all nine products.

 

Ans:

 

 

Chapter 11

Topic:  Allylic Bromination

Section:  11.7

Difficulty Level:  Medium

 

  1. Upon treatment with NBS and irradiation with UV light, 2-propyl-1-pentene produces exactly four monobrominated compounds (including stereoisomers).  Draw and name the products of this reaction.

 

 

Ans:

 

Chapter 11

Topic:  Allylic Bromination

Section:  11.7

Difficulty Level:  Medium

 

  1. Upon treatment with NBS and irradiation with UV light, 1-ethyl-4-methylbenzene produces exactly three monobrominated compounds (including stereoisomers).  Draw the products of this reaction.

 

Ans:

 

Chapter 11

Topic:  Allylic Bromination

Section:  11.7

Difficulty Level:  Easy

 

  1. Upon treatment with NBS and irradiation with UV light, 2-isopropyl-3-methyl-1-butene reacts to produce exactly two monobrominated compounds.  Draw the products of this reaction.

 

Ans:

 

Chapter 11

Topic:  Allylic Bromination

Section:  11.7

Difficulty Level:  Medium

 

  1. Upon treatment with NBS and irradiation with UV light, 2-methyl-2-butene reacts to produce exactly six monobrominated compounds.  Draw the products of this reaction.

 

 

Ans:

 

Chapter 11

Topic:  Atmospheric Chemistry and the Ozone Layer

Section:  11.8

Difficulty Level:  Easy

 

  1. Which of the following compounds would be expected to be least destructive to the ozone layer?

 

 

Ans:  D

 

Chapter 11

Topic:  Atmospheric Chemistry and the Ozone Layer

Section:  11.8

Difficulty Level:  Easy

 

  1. Which of the following shows the correct products initially formed (first step) when ozone absorbs ultraviolet light?

 

 

 

Ans:  A

 

 

Chapter 11

Topic:  Atmospheric Chemistry and the Ozone Layer

Section:  11.8

Difficulty Level:  Medium

 

  1. Use correct arrow formalism to show the second propagation step for the reaction of a chlorine radical with ozone.

 

Ans:

 

Chapter 11

Topic:  Autooxidation and Antioxidants

Section:  11.9

Difficulty Level:  Easy

 

  1. Use correct arrow formalism to show the propagation steps for the autooxidation of diethyl ether.

 

Ans:

 

Chapter 11

Topic:  Autooxidation and Antioxidants

Section:  11.9

Difficulty Level:  Easy

 

  1. Which of the following is expected to be a major product for the reaction shown below?

 

  1. I
  2. II
  3. III
  4. IV

 

 

Ans:  B

 

 

Chapter 11

Topic:  Autooxidation and Antioxidants

Section:  11.9

Difficulty Level:  Easy

 

  1. Which of the following is expected to function as an antioxidant?

 

 

  1. I
  2. II
  3. III
  4. IV
  5. I, II, III, and IV

 

Ans:  C

 

Chapter 11

Topic:  Autooxidation and Antioxidants

Section:  11.9

Difficulty Level:  Easy

 

  1. Which term best describes the process shown below?

 

 

 

  1. neutralization
  2. propagation
  3. termination
  4. initiation
  5. elimination

 

Ans:  B

 

Chapter 11

Topic:  Autooxidation and Antioxidants

Section:  11.9

Difficulty Level:  Easy

 

  1. Which term best describes the process shown below?

 

 

 

  1. initiation
  2. propagation
  3. termination
  4. elimination
  5. inhibition

 

Ans:  C

 

Chapter 11

Topic:  Radical Addition of HBr

Section:  11.10

Difficulty Level:  Easy

 

  1. Predict the major product(s) of the reaction shown below:

 

  1. I
  2. II
  3. III
  4. IV
  5. II and III

 

Ans:  A

 

Chapter 11

Topic:  Radical Addition of HBr

Section:  11.10

Difficulty Level:  Easy

 

  1. Predict the major product(s) of the reaction shown below:

 

 

  1. I
  2. II
  3. III
  4. IV
  5. II and III

 

Ans:  E

 

 

Chapter 11

Topic:  Radical Addition of HBr

Section:  11.10

Difficulty Level:  Easy

 

  1. Which intermediate leads to the major product for the reaction of 2-methyl-2-butene with hydrogen bromide and hydrogen peroxide?

 

 

  1. I
  2. II
  3. III
  4. IV

 

Ans:  B

 

Chapter 11

Topic:  Radical Addition of HBr

Section:  11.10

Difficulty Level:  Easy

 

  1. Which intermediate leads to the major product for the reaction of 2-methyl-2-butene with hydrogen bromide?

 

 

  1. I
  2. II
  3. III
  4. IV
  5. None of the above

 

Ans:  E

 

Chapter 11

Topic:  Radical Addition of HBr

Section:  11.10

Difficulty Level:  Easy

 

  1. Predict the product(s) of the following reaction:
    1. I
    2. II
    3. III
    4. I, II
    5. I, II, III, IV

 

Ans:  E

 

 

Chapter 11

Topic:  Radical Addition of HBr

Section:  11.10

Difficulty Level:  Easy

 

  1. Predict the product(s) of the following reaction:
    1. I
    2. II
    3. III
    4. I, II
    5. I, II, III, IV

 

Ans:  B

 

Chapter 11

Topic:  Radical Addition of HBr

Section:  11.10

Difficulty Level:  Difficult

 

  1. Of the four choices shown, which is likely to be a major product of the reaction below?

 

  1. I
  2. II
  3. III
  4. IV

 

Ans:  A

 

Chapter 11

Topic:  Radical Addition of HBr

Section:  11.10

Difficulty Level:  Difficult

 

  1. Compound A, C6H12 reacts with HBr/ROOR to give compound B, C6H13 Compound C, C6H14, reacts with bromine and light to produce compound B, C6H13Br.  Suggest structures for compounds A, B, and C.

 

Ans:

 

Chapter 11

Topic:  Radical Addition of HBr

Section:  11.10

Difficulty Level:  Easy

 

  1. Which of the following steps is thermodynamically unfavorable at all temperatures?

 

 

Ans:  D

 

 

Chapter 11

Topic:  Radical Addition of HBr

Section:  11.10

Difficulty Level:  Easy

 

  1. Use correct arrow formalism to show the propagation steps for the following reaction.

Chapter 11

Topic:  Radical Polymerization

Section:  11.11

Difficulty Level:  Easy

 

  1. Determine the repeat unit for the polymer produced in the following reaction.

 

 

Chapter 11

Topic:  Radical Polymerization

Section:  11.11

Difficulty Level:  Easy

 

  1. Which of the following is the repeat unit for the polymer produced in the following reaction?

 

 

 

 

Chapter 11

Topic:  Radical Polymerization

Section:  11.11

Difficulty Level:  Easy

 

  1. Poly(methyl methacrylate) (PMMA) is a light, shatter-resistant plastic prepared by the free-radical polymerization of methyl methacrylate (shown below). What is the repeat unit of PMMA?

 

 

Chapter 11

Topic:  Radical Polymerization

Section:  11.11

Difficulty Level:  Difficult

 

  1. Polychloroprene (Neoprene) can be prepared by the free-radical polymerization of chloroprene. Use correct arrow formalism to show the propagation steps that lead to the isomer of polychloroprene shown below.

 

 

 

Chapter 11

Topic:  Radical Polymerization

Section:  11.11

Difficulty Level:  Difficult

 

  1. Propylene (propene) undergoes free radical polymerization with benzoyl peroxide, but does not produce very long chains. Provide a reasonable explanation for this result.

 

Ans:  There are C-H bonds at allylic positions in propylene.  Hydrogen abstraction from this allylic position competes with reaction with the double bond.  If abstraction occurs by a growing chain, that chain ends.

 

 

 

Chapter 11

Topic:  Radical Polymerization

Section:  11.11

Difficulty Level:  Medium

 

  1. The free radical polymerization of styrene with benzoyl peroxide yields a polymer that has repeat units arranged primarily in a ‘head-to-tail’ arrangement. This means that the phenyl group primarily ends up placed at alternating carbon atoms along the chain.  Use correct arrow formalism to show why this arrangement is preferred over a ‘head-to-head’ or ‘tail-to-tail’ arrangement.

Ans:  The ‘head-to-tail’ addition gives a stabilized radical.  Both ‘head-to-head’ and ‘tail-to-tail’ give unstable primary radicals.

 

Chapter 11

Topic:  Radical Polymerization

Section:  11.11

Difficulty Level:  Difficult

 

  1. Your mentions that the free radical polymerization of ethylene can produce branches. Although branches of various lengths are possible, butyl branches are very common.  Suggest an explanation for this fact.

 

Ans:  As the chain grows, the motion of the end of the chain brings the reactive radical close to hydrogen atoms in the chain.  A particularly stable transition state is one in which a six-membered ‘ring’ is formed.  If hydrogen abstraction occurs from this transition state, the new radical can react with addition monomer, and a butyl branch is formed (see below).

 

 

Chapter 11

Topic:  Radical Polymerization

Section:  11.11

Difficulty Level:  Easy

 

  1. Use correct arrow formalism to show termination by coupling of two growing poly(vinyl chloride) chains.

 

 

Ans:

 

Chapter 11

Topic:  Radical Polymerization

Section:  11.11

Difficulty Level:  Easy

 

  1. Azobisisobutyronitrile (AIBN) is commonly used as a radical initiator. Use correct arrow formalism to show this process.

 

Ans:

 

Chapter 11

Topic:  Radical Polymerization

Section:  11.11

Difficulty Level:  Easy

 

  1. Which monomer is used for the synthesis of Teflon?

 

  1. 1,1-difluoroethene
  2. 1,1,2,2-tetrafluoropropene
  3. 1,1,2,2-tetrafluoroethene
  4. tetrafluoromethane

 

Ans:  C

 

Chapter 11

Topic:  Radical Polymerization

Section:  11.11

Difficulty Level:  Easy

 

  1. Which monomer is used for the synthesis of poly(vinyl chloride)?

 

  1. 1-chloroethene
  2. 1-chloroethane
  3. 1,2-dichloroethene
  4. 1-chloro-1-propene

 

Ans:  A

 

Chapter 11

Topic:  Radical Processes in the Petrochemical Industry

Section:  11.12

Difficulty Level:  Easy

 

  1. Thermal cracking of butane can produce ethyl radicals via homolytic cleavage. Use correct arrow formalism to show this process.

 

Ans:

 

Chapter 11

Topic:  Radical Processes in the Petrochemical Industry

Section:  11.12

Difficulty Level:  Easy

 

  1. One possible product of thermal cracking of hexane is 1-butene. Use correct arrow formalism to suggest a possible mechanism for this process starting from an alkyl radical.

 

Ans:

 

Chapter 11

Topic:  Radical Processes in the Petrochemical Industry

Section:  11.12

Difficulty Level:  Easy

 

  1. Draw the product of coupling of the following radicals.

 

Ans:

 

Chapter 11

Topic:  Halogenation as a Synthetic Technique

Section:  11.13

Difficulty Level:  Easy

 

  1. Propose an efficient synthesis of 1-iodo-2-methylpropane from 2-methylpropene.

 

Ans:

 

Chapter 11

Topic:  Halogenation as a Synthetic Technique

Section:  11.13

Difficulty Level:  Easy

 

  1. Propose an efficient synthesis of 2-methylpropene from 2-methylpropane.

 

Ans:

 

Chapter 11

Topic:  Halogenation as a Synthetic Technique

Section:  11.13

Difficulty Level:  Easy

 

  1. Propose an efficient synthesis of polyethylene from ethane.

 

Ans:

 

Chapter 11

Topic:  Halogenation as a Synthetic Technique

Section:  11.13

Difficulty Level:  Medium

 

  1. Propose an efficient synthesis of 3,4-dimethyl-2-pentanol using 2-methyl-2-butene and ethanol as your sources of carbon.

 

Ans:

 

 

Chapter 11

Topic:  Halogenation as a Synthetic Technique

Section:  11.13

Difficulty Level:  Medium

 

  1. Propose an efficient sequence of reactions to accomplish the following transformation.

 

 

Ans: 1.  Br2, light

  1. potassium t-butoxide
  2. mCPBA
  3. H3O+

 

Chapter 11

Topic:  Halogenation as a Synthetic Technique

Section:  11.13

Difficulty Level:  Medium

 

  1. Propose an efficient synthesis of 4-penten-2-ol from propene.

 

Ans:

 

Chapter 11

Topic:  Halogenation as a Synthetic Technique

Section:  11.13

Difficulty Level:  Difficult

 

  1. Propose an efficient synthesis of 2-butyn-1-ol from propane.

 

Ans:

 

 

Chapter 11

Topic:  Halogenation as a Synthetic Technique

Section:  11.13

Difficulty Level:  Medium

 

  1. Propose an efficient sequence of reactions to accomplish the following transformation.

 

 

 

 

Chapter 11

Topic:  Halogenation as a Synthetic Technique

Section:  11.13

Difficulty Level:  Medium

 

  1. Propose an efficient sequence of reactions to accomplish the following transformation.

 

 

 

Chapter 11

Topic:  Halogenation as a Synthetic Technique

Section:  11.13

Difficulty Level:  Medium

 

  1. Propose an efficient sequence of reactions to accomplish the following transformation.

 

Chapter 11

Topic:  Halogenation as a Synthetic Technique + Spectroscopy

Section:  11.13 + Spectroscopy

Difficulty Level:  Hard

 

  1. 99. Methylenecyclopentane (below) can be exposed to allylic bromination conditions to give multiple regioisomeric compounds, including Compound X. Compound X can then be hydrogenated to give Compound Y, which has only 4 distinct resonances in the (proton-decoupled) 13C NMR spectrum.  What are the structures of compounds X and Y?

 

Ans:

 

 

Chapter 11

Topic:  Halogenation as a Synthetic Technique + Spectroscopy

Section:  11.13 + Spectroscopy

Difficulty Level:  Medium

 

  1. 100. When 2-methyl-1-propene is exposed to NBS and UV light, only one major product is obtained. How many distinct resonances in the (proton-decoupled) 13C NMR spectrum are observed in the product?

 

Ans:  4

 

 

 

Chapter 11

Topic:  Halogenation as a Synthetic Technique + Spectroscopy

Section:  11.13 + Spectroscopy

Difficulty Level:  Medium

 

  1. 101. When 1,1,4-trimethylcyclohexane is exposed to Br2 and UV light, only one major product is obtained. How many distinct resonances in the (proton-decoupled) 13C NMR spectrum are observed in the product?

 

Ans:  6

 

 

 

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