Question 1

What product is formed when 5-chloro-1-methylcyclohexene is reduced with a Pt catalyst and H2?

Accepted Answer

A) 1-chloro-5-methylcyclohexane 
B) 1-chloro-3-methylcyclohexane 
C) 5-chloro-1-methylcyclohexane 
D) 3-chloro-1-methylcyclohexane 
E) None of the above 
A) 1-chloro-5-methylcyclohexane 
B) 1-chloro-3-methylcyclohexane 
C) 5-chloro-1-methylcyclohexane 
D) 3-chloro-1-methylcyclohexane 
E) None of the above B

Question 2

The regioselectivity and stereospecificity in the oxymercuration-demercuration of an alkene is best described as:

Accepted Answer

A) Markovnikov orientation with syn-addition 
B) Markovnikov orientation with anti-addition 
C) anti-Markovnikov orientation with syn-addition 
D) anti-Markovnikov orientation with anti-addition 
E) Markonikov orientation with both syn- and anti-addition 
A) Markovnikov orientation with syn-addition 
B) Markovnikov orientation with anti-addition 
C) anti-Markovnikov orientation with syn-addition 
D) anti-Markovnikov orientation with anti-addition 
E) Markonikov orientation with both syn- and anti-addition B

Question 3

What synthetic goal is achieved by subjecting an alkene to an oxymercuration-demercuration reaction sequence?

Accepted Answer

A) Markovnikov addition of H2O,promoting skeletal rearrangement 
B) Markovnikov addition of H2O,preventing skeletal rearrangement 
C) anti-Markovnikov addition of H2O,promoting skeletal rearrangement 
D) anti-Markovnikov addition of H2O,preventing skeletal rearrangement 
E) anti-Markovnikov addition of H2O,syn-hydroxylation 
A) Markovnikov addition of H2O,promoting skeletal rearrangement 
B) Markovnikov addition of H2O,preventing skeletal rearrangement 
C) anti-Markovnikov addition of H2O,promoting skeletal rearrangement 
D) anti-Markovnikov addition of H2O,preventing skeletal rearrangement 
E) anti-Markovnikov addition of H2O,syn-hydroxylation B

Question 4

What is the expected major product upon reaction of 1-pentene with Cl2?

Accepted Answer

A) 1-chloropentane 
B) 2-chloropentane 
C) 1,1-dichloropentane 
D) 2,2-dichloropentane 
E) 1,2-dichloropentane 
A) 1-chloropentane 
B) 2-chloropentane 
C) 1,1-dichloropentane 
D) 2,2-dichloropentane 
E) 1,2-dichloropentane

Question 5

What is the expected major product for 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 6

To accomplish a Markovnikov addition of water to an unsymmetrical alkene,with minimal skeletal rearrangement,the best reagents would be:

Accepted Answer

A) water and dilute acid 
B) water and concentrated acid 
C) 1)Hg(OAc)2,H2O 2.NaBH4,NaOH 
D) 1)BH3•THF 2.H2O2,NaOH 
E) 1)OsO4,pyridine 2.NaHSO3,H2O 
A) water and dilute acid 
B) water and concentrated acid 
C) 1)Hg(OAc)2,H2O 2.NaBH4,NaOH 
D) 1)BH3•THF 2.H2O2,NaOH 
E) 1)OsO4,pyridine 2.NaHSO3,H2O

Question 7

In conducting a catalytic hydrogenation of an alkene,which catalyst listed is most likely soluble in the reaction medium?

Accepted Answer

A) Ni 
B) Pt 
C) Pd 
D) Wilkinson 
E) All of the above are soluble 
A) Ni 
B) Pt 
C) Pd 
D) Wilkinson 
E) All of the above are soluble

Question 8

The rule that correctly predicts the regiochemistry of most ionic additions to alkenes is called ____________________.

Accepted Answer

The answer of The rule that correctly predicts the regiochemistry...

Question 9

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

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 10

Treating 2-methyl-2-pentene with Br2 is expected to produce which of the following as the major product?

Accepted Answer

A) 2,3-dibromo-2-methylpentane 
B) 2,2-dibromo-2-methylpentane 
C) 3,3-dibromo-2-methylpentane 
D) 2-bromo-2-methylpentane 
E) 3-dibromo-2-methylpentane 
A) 2,3-dibromo-2-methylpentane 
B) 2,2-dibromo-2-methylpentane 
C) 3,3-dibromo-2-methylpentane 
D) 2-bromo-2-methylpentane 
E) 3-dibromo-2-methylpentane

Question 11

The expected intermediate formed during a halohydrin reaction is:

Accepted Answer

A) a halonium ion. 
B) the most stable carbocation with OH on the adjacent carbon. 
C) the most stable carbocation with X on the adjacent carbon. 
D) a cyclic oxonium ion. 
E) the most stable carbanion. 
A) a halonium ion. 
B) the most stable carbocation with OH on the adjacent carbon. 
C) the most stable carbocation with X on the adjacent carbon. 
D) a cyclic oxonium ion. 
E) the most stable carbanion.

Question 12

How many moles of hydrogen (H2)are required to completely reduce 1 mole of cis-2,3,3-trimethylhepta-1,5-diene?

Accepted Answer

A) 02 
B) 1 
C) 2 
D) 3 
E) 4 
A) 02 
B) 1 
C) 2 
D) 3 
E) 4

Question 13

For the catalytic hydrogenation of alkenes,select from below those most likely to function as a homogenous catalyst?

Accepted Answer

A) Wilkinson 
B) Ni 
C) Pd 
D) Pt 
E) Au 
A) Wilkinson 
B) Ni 
C) Pd 
D) Pt 
E) Au

Question 14

Any proper mechanism of hydroboration-oxidation must explain the observed _________ addition of the H and OH to the alkene as well as the _____________ regiochemistry.

Accepted Answer

syn,anti-M

Question 15

In the addition reaction of HI to 2-methyl-2-butene,the Markovnikov addition mechanism involves:

Accepted Answer

A) attack of 2-methyl-2-butene initiated by an iodide ion. 
B) attack of 2-methyl-2-butene initiated by an iodine atom. 
C) isomerization of 2-iodo-2-methylbutene. 
D) formation of a carbocation at carbon two (C-2). 
E) formation of carbocation at carbon three (C-3). 
A) attack of 2-methyl-2-butene initiated by an iodide ion. 
B) attack of 2-methyl-2-butene initiated by an iodine atom. 
C) isomerization of 2-iodo-2-methylbutene. 
D) formation of a carbocation at carbon two (C-2). 
E) formation of carbocation at carbon three (C-3).

Question 16

The regioselectivity and stereospecificity in the hydroboration-oxidation of an alkene is best described as:

Accepted Answer

A) Markovnikov orientation with syn-addition 
B) Markovnikov orientation with anti-addition 
C) Anti-Markovnikov orientation with syn-addition 
D) Anti-Markovnikov orientation with anti-addition 
E) Markovnikov orientation with both syn- and anti-addition 
A) Markovnikov orientation with syn-addition 
B) Markovnikov orientation with anti-addition 
C) Anti-Markovnikov orientation with syn-addition 
D) Anti-Markovnikov orientation with anti-addition 
E) Markovnikov orientation with both syn- and anti-addition

Question 17

In an addition reaction to an alkene,the π bond plays the role of:

Accepted Answer

A) nucleophile 
B) electrophile 
C) leaving group 
D) A and B 
E) B and C 
A) nucleophile 
B) electrophile 
C) leaving group 
D) A and B 
E) B and C

Question 18

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 19

Which statement is true about the temperature dependence of an addition reaction?

Accepted Answer

A) Addition reactions are thermodynamically favorable at all temperatures. 
B) Addition reactions are thermodynamically disfavored at all temperatures. 
C) Addition reactions are thermodynamically favorable at low temperatures. 
D) Addition reactions are thermodynamically favorable at high temperatures. 
E) Addition reactions are thermodynamically impossible. 
A) Addition reactions are thermodynamically favorable at all temperatures. 
B) Addition reactions are thermodynamically disfavored at all temperatures. 
C) Addition reactions are thermodynamically favorable at low temperatures. 
D) Addition reactions are thermodynamically favorable at high temperatures. 
E) Addition reactions are thermodynamically impossible.

Question 20

Which of the following alkene addition reactions occur(s)specifically in an anti fashion?

Accepted Answer

A) hydroboration-oxidation 
B) addition of Br2 
C) addition of H2 
D) addition of H2O in dilute acid 
E) both A and B 
A) hydroboration-oxidation 
B) addition of Br2 
C) addition of H2 
D) addition of H2O in dilute acid 
E) both A and B

Exam 9: Addition Reactions of Alkenes

What product is formed when 5-chloro-1-methylcyclohexene is reduced with a Pt catalyst and H2?

The regioselectivity and stereospecificity in the oxymercuration-demercuration of an alkene is best described as:

What synthetic goal is achieved by subjecting an alkene to an oxymercuration-demercuration reaction sequence?

What is the expected major product upon reaction of 1-pentene with Cl2?

What is the expected major product for the hydrogenation of an alkene?

To accomplish a Markovnikov addition of water to an unsymmetrical alkene,with minimal skeletal rearrangement,the best reagents would be:

In conducting a catalytic hydrogenation of an alkene,which catalyst listed is most likely soluble in the reaction medium?

The rule that correctly predicts the regiochemistry of most ionic additions to alkenes is called ____________________.

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

Treating 2-methyl-2-pentene with Br2 is expected to produce which of the following as the major product?

The expected intermediate formed during a halohydrin reaction is:

How many moles of hydrogen (H2)are required to completely reduce 1 mole of cis-2,3,3-trimethylhepta-1,5-diene?

For the catalytic hydrogenation of alkenes,select from below those most likely to function as a homogenous catalyst?

Any proper mechanism of hydroboration-oxidation must explain the observed _________ addition of the H and OH to the alkene as well as the _____________ regiochemistry.

In the addition reaction of HI to 2-methyl-2-butene,the Markovnikov addition mechanism involves:

The regioselectivity and stereospecificity in the hydroboration-oxidation of an alkene is best described as:

In an addition reaction to an alkene,the π bond plays the role of:

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

Which statement is true about the temperature dependence of an addition reaction?

Which of the following alkene addition reactions occur(s)specifically in an anti fashion?

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

Molecular Representations

Acids and Bases

Alkanes and Cycloalkanes

Stereoisomerism

Chemical Reactivity and Mechanisms

Substitution Reactions

Alkenes: Structure and Preparation Via Elimination Reactions

Alkynes

Radical Reactions

Synthesis

Alcohols and Phenols

Ethers and Epoxides; Thiols and Sulfides

Nuclear Magnetic Resonance Spectroscopy

Infrared Spectroscopy and Mass Spectrometry

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

Carbohydrates

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

What product is formed when 5-chloro-1-methylcyclohexene is reduced with a Pt catalyst and H₂?

What is the expected major product upon reaction of 1-pentene with Cl₂?

Treating 2-methyl-2-pentene with Br₂ is expected to produce which of the following as the major product?

How many moles of hydrogen (H₂)are required to completely reduce 1 mole of cis-2,3,3-trimethylhepta-1,5-diene?

Any proper mechanism of hydroboration-oxidation must explain the observed _ addition of the H and OH to the alkene as well as the _____ regiochemistry.