Question 1

Which of the following is the major product of the reaction shown?

Accepted Answer

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

Question 2

Which of the reagents below are expected to convert cyclopentene into cyclopentane?

Accepted Answer

A)  H2 and Ni 
B)  H2O 
C)  Heat 
D)  Zn, H3O+ 
E)  Light 
A)  H2 and Ni 
B)  H2O 
C)  Heat 
D)  Zn, H3O+ 
E)  Light

Question 3

Identify the product from the hydrogenation of an alkene.

Accepted Answer

A)  dihaloalkane 
B)  alkane 
C)  haloalkane 
D)  alcohol 
E)  ether 
A)  dihaloalkane 
B)  alkane 
C)  haloalkane 
D)  alcohol 
E)  ether

Question 4

Which of the given reaction schemes would produce the molecule shown below?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  Both I and II 
E)  Both II and III 
A)  I 
B)  II 
C)  III 
D)  Both I and II 
E)  Both II and III

Question 5

What is the major product for the following 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 6

Which of the structures shown depicts the most stable carbocation intermediate formed in the hydrohalogenation reaction shown?

Accepted Answer

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

Question 7

Which of the catalysts listed are used in the homogenous catalytic hydrogenation of alkenes? I. Ni II. Pt III. Wilkinson's catalyst

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  I and II 
E)  II and III 
A)  I 
B)  II 
C)  III 
D)  I and II 
E)  II and III

Question 8

For this question, the "entropy term" refers to "-TΔS". Addition reactions are generally favorable at low temperatures because ________.

Accepted Answer

A)  the positive enthalpy term is larger than the negative entropy term 
B)  the negative enthalpy term is larger than the positive entropy term 
C)  the positive enthalpy term is smaller than the negative entropy term 
D)  the negative enthalpy term is smaller than the positive entropy term 
E)  the enthalpy and entropy terms are equal 
A)  the positive enthalpy term is larger than the negative entropy term 
B)  the negative enthalpy term is larger than the positive entropy term 
C)  the positive enthalpy term is smaller than the negative entropy term 
D)  the negative enthalpy term is smaller than the positive entropy term 
E)  the enthalpy and entropy terms are equal

Question 9

How many carbonyl groups are generated upon treatment of the molecule below with ozone, followed by zinc metal and water?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
E)  8 
A)  1 
B)  2 
C)  3 
D)  4 
E)  8

Question 10

Provide the structure(s) of the expected major organic product(s) generated upon completion of the following reaction scheme:

Accepted Answer

The answer of Provide the structure(s) of the expected major...

Question 11

For the reaction sequence below, identify the expected major products.

Accepted Answer

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

Question 12

Most π bonds are quite prone to reaction with an ____________________, also referred to as electron-seeking reagents.

Accepted Answer

The answer of Most π bonds are quite prone to...

Question 13

For the following reaction sequence provide the expected major organic product(s). Include all stereoisomers showing relevant stereochemistry.

Accepted Answer

The answer of For the following reaction sequence provide the...

Question 14

Wilkinson's catalyst accomplishes which of the listed molecular syntheses?

Accepted Answer

A)  syn addition of H2 to an alkene 
B)  anti addition of H2 to an alkene 
C)  syn dihydroxylation of an alkene 
D)  anti dihydroxylation of an alkene 
E)  oxidative cleavage of an alkene 
A)  syn addition of H2 to an alkene 
B)  anti addition of H2 to an alkene 
C)  syn dihydroxylation of an alkene 
D)  anti dihydroxylation of an alkene 
E)  oxidative cleavage of an alkene

Question 15

What would be the optimal conditions to effect the following synthesis?

Accepted Answer

A)  dilute aqueous H2SO4 
B)  concentrated H2SO4 
C)  dilute aqueous HBr 
D)  concentrated HBr 
A)  dilute aqueous H2SO4 
B)  concentrated H2SO4 
C)  dilute aqueous HBr 
D)  concentrated HBr

Question 16

Which is the correct sequence of steps necessary to complete the following reaction?

Accepted Answer

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

Question 17

For the reaction sequence shown, what is the expected major product?

Accepted Answer

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

Question 18

Which reagents are most likely to accomplish the reaction shown below?

Accepted Answer

A)  1. BH3∙THF / 2. HO-, H2O2, H2O 
B)  H+, H2O 
C)  1. Hg(OAc)2, H2O, THF / 2. NaBH4 
D)  1. Hg(OAc)2, CH3OH / 2. NaBH4 
E)  NaOH, H2O 
A)  1. BH3∙THF / 2. HO-, H2O2, H2O 
B)  H+, H2O 
C)  1. Hg(OAc)2, H2O, THF / 2. NaBH4 
D)  1. Hg(OAc)2, CH3OH / 2. NaBH4 
E)  NaOH, H2O

Question 19

For the complete reduction of 1 mole of 3E,5E.-hepta-1,3,5-triene with H2 using a Pd catalyst, how many moles of H2 are consumed?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
E)  5 
A)  1 
B)  2 
C)  3 
D)  4 
E)  5

Question 20

The Markovnikov product resulting from an addition reaction to an unsymmetrical alkene is formed because _____________.

Accepted Answer

A)  the product is statistically favored 
B)  steric hindrance favors its formation 
C)  the reaction proceeds via the more/most stable carbocation 
D)  the reaction forms the more/most stable product 
E)  All of the above are valid reasons 
A)  the product is statistically favored 
B)  steric hindrance favors its formation 
C)  the reaction proceeds via the more/most stable carbocation 
D)  the reaction forms the more/most stable product 
E)  All of the above are valid reasons

Exam 8: Addition Reactions of Alkenes

Which of the following is the major product of the reaction shown?

Which of the reagents below are expected to convert cyclopentene into cyclopentane?

Identify the product from the hydrogenation of an alkene.

Which of the given reaction schemes would produce the molecule shown below?

What is the major product for the following reaction sequence?

Which of the structures shown depicts the most stable carbocation intermediate formed in the hydrohalogenation reaction shown?

Which of the catalysts listed are used in the homogenous catalytic hydrogenation of alkenes? I. Ni II. Pt III. Wilkinson's catalyst

For this question, the "entropy term" refers to "-TΔS". Addition reactions are generally favorable at low temperatures because ________.

How many carbonyl groups are generated upon treatment of the molecule below with ozone, followed by zinc metal and water?

Provide the structure(s) of the expected major organic product(s) generated upon completion of the following reaction scheme:

For the reaction sequence below, identify the expected major products.

Most π bonds are quite prone to reaction with an ____________________, also referred to as electron-seeking reagents.

For the following reaction sequence provide the expected major organic product(s). Include all stereoisomers showing relevant stereochemistry.

Wilkinson's catalyst accomplishes which of the listed molecular syntheses?

What would be the optimal conditions to effect the following synthesis?

Which is the correct sequence of steps necessary to complete the following reaction?

For the reaction sequence shown, what is the expected major product?

Which reagents are most likely to accomplish the reaction shown below?

For the complete reduction of 1 mole of 3E,5E.-hepta-1,3,5-triene with H2 using a Pd catalyst, how many moles of H2 are consumed?

The Markovnikov product resulting from an addition reaction to an unsymmetrical alkene is formed because _____________.

A Review of General Chemistry: Electrons, Bonds, and Molecular Properties

Molecular Representations

Acids and Bases

Alkanes and Cycloalkanes

Stereoisomerism

Chemical Reactivity and Mechanisms

Alkyl Halides: Nucleophilic Substitution and Elimination Reactions

Alkynes

Radical Reactions

Synthesis

Alcohols and Phenols

Ethers and Epoxides; Thiols and Sulfides

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Conjugated Pi Systems and Pericyclic Reactions

Aromatic Compounds

Aromatic Substitution Reactions

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Alpha Carbon Chemistry: Enols and Enolates

Amines

Introduction to Organometallic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

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For the complete reduction of 1 mole of 3E,5E.-hepta-1,3,5-triene with H₂ using a Pd catalyst, how many moles of H₂ are consumed?