Question 1

What sequence of reactions could be used to prepare cis-1,2-cyclopentanediol from cyclopentane?

Accepted Answer

A)  (1)Cl2,h$\nu$; (2)t-BuOK/t-BuOH; (3)OsO4; (4)NaHSO3/H2O 
B)  (1)t-BuOK/t-BuOH; (2)Cl2,h$\nu$; (3)NaOH/H2O 
C)  (1)Cl2,h$\nu$; (2)t-BuOK/t-BuOH; (3)H2O2 
D)  (1)NaOH/H2O; (2)Br2; (3)NaNH2(2eq. )/liq.NH3; (4)KMnO4,NaOH/H2O,5°C 
E)  (1)Cl2,h$\nu$; (2)t-BuOK/t-BuOH; (3)Hg(OAc)2,H2O (4)NaBH4,H3O+ 
A)  (1)Cl2,h$\nu$; (2)t-BuOK/t-BuOH; (3)OsO4; (4)NaHSO3/H2O 
B)  (1)t-BuOK/t-BuOH; (2)Cl2,h$\nu$; (3)NaOH/H2O 
C)  (1)Cl2,h$\nu$; (2)t-BuOK/t-BuOH; (3)H2O2 
D)  (1)NaOH/H2O; (2)Br2; (3)NaNH2(2eq. )/liq.NH3; (4)KMnO4,NaOH/H2O,5°C 
E)  (1)Cl2,h$\nu$; (2)t-BuOK/t-BuOH; (3)Hg(OAc)2,H2O (4)NaBH4,H3O+

Question 2

Which of these molecules is not expected to arise as a product of the high temperature chlorination of methane?

Accepted Answer

A)  CCl4 
B)  HCCl3 
C)  CH2Cl2 
D)  CH3CH3 
E)  CH2=CH2 
A)  CCl4 
B)  HCCl3 
C)  CH2Cl2 
D)  CH3CH3 
E)  CH2=CH2

Question 3

The bond dissociation energies for the relevant bonds are given below each of the species involved in the following reaction.Calculate the overall $\Delta$H° for the reaction.

Accepted Answer

A)  +243 kJ / mol 
B)  -138 kJ / mol 
C)  +138 kJ / mol 
D)  -781 kJ / mol 
E)  +781 kJ / mol 
A)  +243 kJ / mol 
B)  -138 kJ / mol 
C)  +138 kJ / mol 
D)  -781 kJ / mol 
E)  +781 kJ / mol

Question 4

Which of the following combinations of reactants can provide a demonstrable example of anti-Markovnikov addition?

Accepted Answer

A)  CH2=CHCH3 + HCl + ROOR 
B)  CH3CH=CH2 + H2O + Cl2 
C)  CH3CH=CHCH3 + HBr + ROOR 
D)  CH3CH2CH=CH2 + HBr + ROOR 
E)  CH3CH2CH=CH2 + Br2 + ROOR 
A)  CH2=CHCH3 + HCl + ROOR 
B)  CH3CH=CH2 + H2O + Cl2 
C)  CH3CH=CHCH3 + HBr + ROOR 
D)  CH3CH2CH=CH2 + HBr + ROOR 
E)  CH3CH2CH=CH2 + Br2 + ROOR

Question 5

Which reaction would you expect to have the smallest energy of activation? $\Delta$H°(kJ mol-1)

Accepted Answer

A)  CH3· + CH3· --$\rightarrow$ CH3CH3 -378 
B)  CH4 + F· --$\rightarrow$CH3· + HF -130 
C)  CH4 + I· --$\rightarrow$CH3· + HI +142 
D)  CH4 + Br· --$\rightarrow$CH3·  + HBr +104 
E)  CH4 + Cl· --$\rightarrow$CH3· + HCl +8 
A)  CH3· + CH3· --$\rightarrow$ CH3CH3 -378 
B)  CH4 + F· --$\rightarrow$CH3· + HF -130 
C)  CH4 + I· --$\rightarrow$CH3· + HI +142 
D)  CH4 + Br· --$\rightarrow$CH3·  + HBr +104 
E)  CH4 + Cl· --$\rightarrow$CH3· + HCl +8

Question 6

How many monochloro derivatives,including stereoisomers,can be formed in the chlorination of 1-bromobutane?

Accepted Answer

A)  4 
B)  5 
C)  6 
D)  7 
E)  8 
A)  4 
B)  5 
C)  6 
D)  7 
E)  8

Question 7

Deduce the structure of a substance,C8H18,which gives only a single monochloro derivative upon reaction with Cl2 under UV irradiation.

Accepted Answer

Question 8

Mono-bromination of the following alkane,   , (using Br2 with light)would be?

Accepted Answer

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

Question 9

What is the product for the following three-step reaction sequence?

Accepted Answer

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

Question 10

What is the total number of trichloropropanes which can be produced by free radical chlorination of propane? Include all stereoisomers.

Accepted Answer

A)  4 
B)  5 
C)  6 
D)  7 
E)  8 
A)  4 
B)  5 
C)  6 
D)  7 
E)  8

Question 11

Which would be the best way to carry out the following synthesis?

Accepted Answer

A)  (1)HA,heat; (2)HBr 
B)  (1)HBr and peroxides; (2)Br2/CCl4 
C)  (1)HA,heat; (2)HBr and peroxides 
D)  (1)Br2/CCl4; (2)HA,heat 
E)  (1)HA,heat; (2)Br2/CCl4 
A)  (1)HA,heat; (2)HBr 
B)  (1)HBr and peroxides; (2)Br2/CCl4 
C)  (1)HA,heat; (2)HBr and peroxides 
D)  (1)Br2/CCl4; (2)HA,heat 
E)  (1)HA,heat; (2)Br2/CCl4

Question 12

Mono-bromination of the following alkane,   , (using Br2 with light)would be?

Accepted Answer

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

Question 13

Which of the following would serve as the best synthesis of 2-bromohexane?

Accepted Answer

A) 
  
B) 
  
C) 
  
D) 
  
E)  All of the above would be equally suitable. 
A) 
  
B) 
  
C) 
  
D) 
  
E)  All of the above would be equally suitable.

Question 14

Which hydrogen would be abstracted first when mono-brominating with Br2 and light?

Accepted Answer

A)  Ha 
B)  Hb 
C)  Hc 
D)  Hd 
E)  He 
A)  Ha 
B)  Hb 
C)  Hc 
D)  Hd 
E)  He

Question 15

Macromolecules made up of many repeating subunits are called ____________.

Accepted Answer

The answer of Macromolecules made up of many repeating subunits...

Question 16

The reaction of Cl2 with a methyl radical has a positive $\Delta$H°.Which of these drawings is the best representation of the transition state of this reaction?

Accepted Answer

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

Question 17

Two radicals that are very important in biological processes are ________________ and __________________.

Accepted Answer

molecular

Question 18

Free radical mono-halogenation of an alkane is typically conducted using bromine versus chlorine because

Accepted Answer

A)  the bromine radical is more reactive and therefore more selective. 
B)  the chlorine radical is more reactive and therefore more selective. 
C)  the chlorine radical is less reactive and therefore more selective. 
D)  the bromine radical is less reactive and therefore more selective. 
E)  None of the above 
A)  the bromine radical is more reactive and therefore more selective. 
B)  the chlorine radical is more reactive and therefore more selective. 
C)  the chlorine radical is less reactive and therefore more selective. 
D)  the bromine radical is less reactive and therefore more selective. 
E)  None of the above

Question 19

Chlorofluorocarbons,or freons,diffuse into the upper atmosphere.There,ultraviolet light initiates a radical chain reaction that has been shown to cause extreme damage to _______________.

Accepted Answer

The answer of Chlorofluorocarbons,or freons,diffuse into the upper atmosphere.There,ultraviolet light...

Question 20

What is the product for the following three-step reaction sequence?

Accepted Answer

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

Exam 10: Radical Reactions

What sequence of reactions could be used to prepare cis-1,2-cyclopentanediol from cyclopentane?

Which of these molecules is not expected to arise as a product of the high temperature chlorination of methane?

The bond dissociation energies for the relevant bonds are given below each of the species involved in the following reaction.Calculate the overall Δ\DeltaΔ H° for the reaction.

Which of the following combinations of reactants can provide a demonstrable example of anti-Markovnikov addition?

Which reaction would you expect to have the smallest energy of activation? Δ\DeltaΔ H°(kJ mol-1)

How many monochloro derivatives,including stereoisomers,can be formed in the chlorination of 1-bromobutane?

Deduce the structure of a substance,C8H18,which gives only a single monochloro derivative upon reaction with Cl2 under UV irradiation.

Mono-bromination of the following alkane, , (using Br2 with light)would be?

What is the product for the following three-step reaction sequence?

What is the total number of trichloropropanes which can be produced by free radical chlorination of propane? Include all stereoisomers.

Which would be the best way to carry out the following synthesis?

Mono-bromination of the following alkane, , (using Br2 with light)would be?

Which of the following would serve as the best synthesis of 2-bromohexane?

Which hydrogen would be abstracted first when mono-brominating with Br2 and light?

Macromolecules made up of many repeating subunits are called ____________.

The reaction of Cl2 with a methyl radical has a positive Δ\DeltaΔ H°.Which of these drawings is the best representation of the transition state of this reaction?

Two radicals that are very important in biological processes are ________________ and __________________.

Free radical mono-halogenation of an alkane is typically conducted using bromine versus chlorine because

Chlorofluorocarbons,or freons,diffuse into the upper atmosphere.There,ultraviolet light initiates a radical chain reaction that has been shown to cause extreme damage to _______________.

What is the product for the following three-step reaction sequence?

Carbon Compounds and Chemical Bonds

Representative Carbon Compounds: Functional Groups, Intermolecular Forces, and Infrared Ir Spectroscopy

An Introduction to Organic Reactions: Acids and Bases

Alkanes: Nomenclature, Conformational Analysis, and an Introduction to Synthesis

Stereochemistry: Chiral Molecules

Ionic Reactions - Nucleophilic Substitution and Elimination Reactions of Alkyl Halides

Alkenes and Alkynes I: Properties and Synthesis, Elimination Reactions of Alkyl Halides

Alkenes and Alkynes Ii: Addition Reactions

Nuclear Magnetic Resonance and Mass Spectrometry: Tools for Structure Determination

Alcohols and Ethers

Alcohols From Carbonyl Compounds Oxidation-Reduction and Organometallic Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group

Aldehydes and Ketones Ii Aldol Reactions

Carboxylic Acids and Their Derivatives Nucleophilic Addition - Elimination at the Acyl Carbon

Synthesis and Reactions of Beta-Dicarbonyl Compounds: More Chemistry of Enolate Ions

Amines

Phenols and Aryl Halides: Nucleophilic Aromatic Substitution

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

Which reaction would you expect to have the smallest energy of activation? $\Delta$ H°(kJ mol^-1)

Deduce the structure of a substance,C₈H₁₈,which gives only a single monochloro derivative upon reaction with Cl₂ under UV irradiation.

Mono-bromination of the following alkane, , (using Br₂ with light)would be?

Mono-bromination of the following alkane, , (using Br₂ with light)would be?

Which hydrogen would be abstracted first when mono-brominating with Br₂ and light?

The reaction of Cl₂ with a methyl radical has a positive $\Delta$ H°.Which of these drawings is the best representation of the transition state of this reaction?

Two radicals that are very important in biological processes are and __.