Question 1

The reagents that could effect the following conversion are: BH3, then H2O2 and NaOH.

Accepted Answer

A) True 
 B)False

Question 2

Which of the following alkenes undergoes the least exothermic hydrogenation upon treatment with H2/Pd?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
A)  1 
B)  2 
C)  3 
D)  4

Question 3

Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of pairs of electrons and the structure of reactive intermediates.

Accepted Answer

The reaction proceeds in three

Question 4

Which of the following reactions of alkenes is stereospecific?

Accepted Answer

A)  addition of HCl (treatment with HCl) 
B)  hydrogenation (treatment with H2/Pt) 
C)  addition of HBr (treatment with HBr) 
D)  acid-catalyzed hydration (treatment with aqueous H2SO4) 
A)  addition of HCl (treatment with HCl) 
B)  hydrogenation (treatment with H2/Pt) 
C)  addition of HBr (treatment with HBr) 
D)  acid-catalyzed hydration (treatment with aqueous H2SO4)

Question 5

What is the major organic product obtained from the following reaction?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
A)  1 
B)  2 
C)  3 
D)  4

Question 6

The reaction of methylpropene with HBr in ether gives one of the two products below as the major product. Answer the following question(s) about this reaction.  
-Product _____ would have a higher energy transition state for the formation of the intermediate leading to it.

Accepted Answer

The answer of The reaction of methylpropene with HBr in...

Question 7

What is the major product obtained upon addition of Br2 to (R)-4-tert-butylcyclohexene?

Accepted Answer

A)  (1R,2R,4R)-1,2-dibromo-4-tert-butylcyclohexane 
B)  (1S,2R,4R)-1,2-dibromo-4-tert-butylcyclohexane 
C)  (1S,2S,4R)-1,2-dibromo-4-tert-butylcyclohexane 
D)  (1S,2S,4S)-1,2-dibromo-4-tert-butylcyclohexane 
A)  (1R,2R,4R)-1,2-dibromo-4-tert-butylcyclohexane 
B)  (1S,2R,4R)-1,2-dibromo-4-tert-butylcyclohexane 
C)  (1S,2S,4R)-1,2-dibromo-4-tert-butylcyclohexane 
D)  (1S,2S,4S)-1,2-dibromo-4-tert-butylcyclohexane

Question 8

Which of the following reactions of alkenes is not stereospecific?

Accepted Answer

A)  bromination (treatment with Br2 in CHCl3) 
B)  hydrogenation (treatment with H2/Pt) 
C)  acid-catalyzed hydration (treatment with aqueous H2SO4) 
D)  bromohydrin formation (treatment with Br2/H2O) 
A)  bromination (treatment with Br2 in CHCl3) 
B)  hydrogenation (treatment with H2/Pt) 
C)  acid-catalyzed hydration (treatment with aqueous H2SO4) 
D)  bromohydrin formation (treatment with Br2/H2O)

Question 9

_____________is the starting material required to produce 3-methyl-1-butanol using the hydroboration-oxidation reaction. (Enter an IUPAC name.)

Accepted Answer

The answer of _____________is the starting material required to produce...

Question 10

What is the best choice of reagent(s) to perform the following transformation?

Accepted Answer

A)  H2O, H2SO4 
B)  Hg(OAc)2 and H2O; followed by NaBH4 
C)  BH3; followed by H2O2, NaOH 
D)  OsO4; followed by NaHSO3 
A)  H2O, H2SO4 
B)  Hg(OAc)2 and H2O; followed by NaBH4 
C)  BH3; followed by H2O2, NaOH 
D)  OsO4; followed by NaHSO3

Question 11

What is the correct order of exothermicity for hydrogenation of the following butenes upon treatment with H2/Pd (more exothermic > less exothermic)?

Accepted Answer

A)  1 > 2 > 3 
B)  1 > 3 > 2 
C)  3 > 2 > 1 
D)  2 > 3 > 1 
A)  1 > 2 > 3 
B)  1 > 3 > 2 
C)  3 > 2 > 1 
D)  2 > 3 > 1

Question 12

What is the major organic product obtained from the following reaction?

Accepted Answer

The answer of What is the major organic product obtained...

Question 13

The reaction of methylpropene with HBr in ether gives one of the two products below as the major product. Answer the following question(s) about this reaction.  
-Product _____ would be formed by a carbocation experiencing the greatest degree of hyperconjugation stabilization.

Accepted Answer

The answer of The reaction of methylpropene with HBr in...

Question 14

Which of the following reactions of alkenes takes place with anti stereospecificity?

Accepted Answer

A)  bishydroxylation (treatment with OsO4 followed by NaHSO3) 
B)  hydrogenation (treatment with H2/Pt) 
C)  addition of HBr (treatment with HBr) 
D)  bromohydrin formation (treatment with Br2, H2O) 
A)  bishydroxylation (treatment with OsO4 followed by NaHSO3) 
B)  hydrogenation (treatment with H2/Pt) 
C)  addition of HBr (treatment with HBr) 
D)  bromohydrin formation (treatment with Br2, H2O)

Question 15

What is the major organic product obtained from the following reaction?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
A)  1 
B)  2 
C)  3 
D)  4

Question 16

What is the best choice of reagent(s) to perform the following transformation?

Accepted Answer

A)  H2O, H2SO4 
B)  Hg(OAc)2 and H2O ; followed by NaBH4 
C)  B2H6; followed by H2O2, NaOH 
D)  OsO4; followed by NaHSO3 
A)  H2O, H2SO4 
B)  Hg(OAc)2 and H2O ; followed by NaBH4 
C)  B2H6; followed by H2O2, NaOH 
D)  OsO4; followed by NaHSO3

Question 17

Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of pairs of electrons and the structure of reactive intermediates.

Accepted Answer

The reaction proceeds in three

Question 18

What is the best choice of reagent(s) to perform the following transformation?

Accepted Answer

A)  O3; followed by (CH3)2S 
B)  Hg(OAc)2 and H2O; followed by NaBH4 
C)  BH3; followed by H2O2, NaOH 
D)  OsO4; followed by NaHSO3 
A)  O3; followed by (CH3)2S 
B)  Hg(OAc)2 and H2O; followed by NaBH4 
C)  BH3; followed by H2O2, NaOH 
D)  OsO4; followed by NaHSO3

Question 19

Identify the given structure given. ​

Accepted Answer

A)  Tetraphenyl phosphate 
B)  BINOL 
C)  BINAP 
D)  Binaphthyl 
A)  Tetraphenyl phosphate 
B)  BINOL 
C)  BINAP 
D)  Binaphthyl

Question 20

What is the major organic product obtained from the following reaction?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
A)  1 
B)  2 
C)  3 
D)  4

Exam 6: Reactions of Alkenes

The reagents that could effect the following conversion are: BH3, then H2O2 and NaOH.

Which of the following alkenes undergoes the least exothermic hydrogenation upon treatment with H2/Pd?

Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of pairs of electrons and the structure of reactive intermediates.

Which of the following reactions of alkenes is stereospecific?

What is the major organic product obtained from the following reaction?

The reaction of methylpropene with HBr in ether gives one of the two products below as the major product. Answer the following question(s) about this reaction. -Product _____ would have a higher energy transition state for the formation of the intermediate leading to it.

What is the major product obtained upon addition of Br2 to (R)-4-tert-butylcyclohexene?

Which of the following reactions of alkenes is not stereospecific?

_____________is the starting material required to produce 3-methyl-1-butanol using the hydroboration-oxidation reaction. (Enter an IUPAC name.)

What is the best choice of reagent(s) to perform the following transformation?

What is the correct order of exothermicity for hydrogenation of the following butenes upon treatment with H2/Pd (more exothermic > less exothermic)?

What is the major organic product obtained from the following reaction?

The reaction of methylpropene with HBr in ether gives one of the two products below as the major product. Answer the following question(s) about this reaction. -Product _____ would be formed by a carbocation experiencing the greatest degree of hyperconjugation stabilization.

Which of the following reactions of alkenes takes place with anti stereospecificity?

What is the major organic product obtained from the following reaction?

What is the best choice of reagent(s) to perform the following transformation?

Provide a neatly drawn mechanism for the following reaction, including curved arrows to show the movement of pairs of electrons and the structure of reactive intermediates.

What is the best choice of reagent(s) to perform the following transformation?

Identify the given structure given. ​

What is the major organic product obtained from the following reaction?

Covalent Bonding and Shapes of Molecules

Alkanes and Cycloalkanes

Stereoisomerism and Chirality

Acids and Bases

Alkenes: Bonding, Nomenclature, and Properties

Alkynes

Haloalkanes, Halogenation, and Radical Reactions

Nucleophilic Substitution and Beta-Elimination

Alcohols

Ethers, Epoxides, and Sulfides

Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Mass Spectrometry

An Introduction to Organometallic Compounds

Aldehydes and Ketones

Carboxylic Acids

Functional Derivatives of Carboxylic Acids

Enolate Anions and Enamines

Dienes, Conjugated Systems, and Pericyclic Reactions

Benzene and the Concept of Aromaticity

Reactions of Benzene and Its Derivatives

Amines

Catalytic Carbon-Carbon Bond Formation

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids

Organic Polymer Chemistry

Filters

The reagents that could effect the following conversion are: BH₃, then H₂O₂ and NaOH.

Which of the following alkenes undergoes the least exothermic hydrogenation upon treatment with H₂/Pd?

What is the major product obtained upon addition of Br₂ to (R)-4-tert-butylcyclohexene?

What is the correct order of exothermicity for hydrogenation of the following butenes upon treatment with H₂/Pd (more exothermic > less exothermic)?

Identify the given structure given.