Question 1

In halohydrin formation the reason why the halohydrin is the major product is because the solvent is more reactive that the bromide nucleophile.

Accepted Answer

A) True 
 B)False

Question 2

What is the major product of the following reaction sequence?

Accepted Answer

A)    
B)    
C)    
D)    
E) More than one of these choices. 
A)    
B)    
C)    
D)    
E) More than one of these choices.

Question 3

(R)-3-Chloro-1-butene reacts with HCl by Markovnikov addition,and the products are separated by gas chromatography.How many total fractions would be obtained and how many would be optically active?

Accepted Answer

A) one optically active fraction only 
B) one optically active fraction and one optically inactive 
C) two optically active fractions 
D) one optically active fraction and two optically inactive 
E) two optically active fractions and one optically inactive 
A) one optically active fraction only 
B) one optically active fraction and one optically inactive 
C) two optically active fractions 
D) one optically active fraction and two optically inactive 
E) two optically active fractions and one optically inactive

Question 4

One mole of an optically active compound,X,with the molecular formula C6H8 reacts with three moles of hydrogen in the presence of a catalyst to yield an optically inactive product that cannot be resolved.X also exhibits IR absorption at approximately 3300 cm-1.Which is a possible structure for X?

Accepted Answer

A) (
E) -4-hexen-1-yne 
B) (Z)-4-hexen-1-yne 
C) (
E) -2-hexen-4-yne 
D) 2-methyl-1-penten-3-yne 
E) 3-methyl-1-penten-4-yne 
A) (
E) -4-hexen-1-yne 
B) (Z)-4-hexen-1-yne 
C) (
E) -2-hexen-4-yne 
D) 2-methyl-1-penten-3-yne 
E) 3-methyl-1-penten-4-yne

Question 5

What is the major product of the following reaction sequence?

Accepted Answer

A)    
B)    
C)    
D)    
E) None of these choices. 
A)    
B)    
C)    
D)    
E) None of these choices.

Question 6

An alkene with the molecular formula C8H16 undergoes ozonolysis to yield a mixture of (CH3)2C=O and (CH3)3CCHO.The alkene is:

Accepted Answer

A) 2,2-Dimethyl-2-hexene 
B) 2,3-Dimethyl-2-hexene 
C) 2,4-Dimethyl-2-hexene 
D) 2,4,4-Trimethyl-2-pentene 
E) More than one of these choices is a possible answer. 
A) 2,2-Dimethyl-2-hexene 
B) 2,3-Dimethyl-2-hexene 
C) 2,4-Dimethyl-2-hexene 
D) 2,4,4-Trimethyl-2-pentene 
E) More than one of these choices is a possible answer.

Question 7

What product would result from the following reaction?

Accepted Answer

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

Question 8

Which of the following would be produced upon ozonolysis of camphene?

Accepted Answer

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

Question 9

What is the major product of the following reaction sequence?

Accepted Answer

A)    
B)    
C)    
D)    
E) None of these choices. 
A)    
B)    
C)    
D)    
E) None of these choices.

Question 10

Even when one or more stereogenic centers are produced as the result of an addition reaction to an alkene,the product is always formed as a racemic mixture.Why is that?

Accepted Answer

Because alkenes are

Question 11

Which reaction would yield a racemic product?

Accepted Answer

A) Cyclopentene + D2/Pt $\to$ 
B) Cyclopentene + OsO4,then Na2SO3 $\to$ 
C) Cyclopentene + Br2/H2O $\to$ 
D) Cyclopentene + cold,dilute KMnO4 $\to$ 
E) Cyclopentene + dilute H2SO4 $\to$ 
A) Cyclopentene + D2/Pt $\to$ 
B) Cyclopentene + OsO4,then Na2SO3 $\to$ 
C) Cyclopentene + Br2/H2O $\to$ 
D) Cyclopentene + cold,dilute KMnO4 $\to$ 
E) Cyclopentene + dilute H2SO4 $\to$

Question 12

Which reaction sequence would convert cis-2-butene to trans-2-butene?

Accepted Answer

A) Br2/CCl4; then 2 NaNH2; then H2/Ni2B(P-2) 
B) Br2/CCl4; then 2 NaNH2; then Li/liq.NH3 
C) H3O+,heat; then cold dilute KMnO4 
D) HBr; then NaNH2; then H2,Pt 
E) None of these choices. 
A) Br2/CCl4; then 2 NaNH2; then H2/Ni2B(P-2) 
B) Br2/CCl4; then 2 NaNH2; then Li/liq.NH3 
C) H3O+,heat; then cold dilute KMnO4 
D) HBr; then NaNH2; then H2,Pt 
E) None of these choices.

Question 13

What is the product(s)formed by treating 3,3 dimethylcyclopentene with H3O+ and heating?

Accepted Answer

A) I only 
B) II and IV 
C) I and III 
D) IV and V 
E) none of these choices 
A) I only 
B) II and IV 
C) I and III 
D) IV and V 
E) none of these choices

Question 14

What is the major product for the following reaction?

Accepted Answer

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

Question 15

What is the major product for the following reaction?

Accepted Answer

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

Question 16

What is the major product of the following reaction sequence?

Accepted Answer

A)    
B)    
C)    
D)    
E) None of these choices. 
A)    
B)    
C)    
D)    
E) None of these choices.

Question 17

What is the major product for the following reaction?

Accepted Answer

A)    
B)    
C)    
D)    
E) None of these choices. 
A)    
B)    
C)    
D)    
E) None of these choices.

Question 18

What would be the major product of the following reaction?

Accepted Answer

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

Question 19

An optically active compound,Y,with the molecular formula C7H12 gives a positive test with cold dilute KMnO4 and shows IR absorption at about 3300 cm-1.On catalytic hydrogenation,Y yields Z(C7H16)and Z is also optically active.Which is a possible structure for Y?

Accepted Answer

A) CH3CH2CH2CH2CH2C$\equiv$CH 
B) (CH3)2CHCH2CH2C$\equiv$CH 
C) CH3CH2CH(CH3)CH2C$\equiv$CH 
D) CH3CH2CH(CH3)C$\equiv$CCH3 
E) CH2=CHCH(CH3)CH2CH=CH2 
A) CH3CH2CH2CH2CH2C$\equiv$CH 
B) (CH3)2CHCH2CH2C$\equiv$CH 
C) CH3CH2CH(CH3)CH2C$\equiv$CH 
D) CH3CH2CH(CH3)C$\equiv$CCH3 
E) CH2=CHCH(CH3)CH2CH=CH2

Question 20

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...

Exam 8: Alkenes and Alkynes II

In halohydrin formation the reason why the halohydrin is the major product is because the solvent is more reactive that the bromide nucleophile.

What is the major product of the following reaction sequence?

(R)-3-Chloro-1-butene reacts with HCl by Markovnikov addition,and the products are separated by gas chromatography.How many total fractions would be obtained and how many would be optically active?

One mole of an optically active compound,X,with the molecular formula C6H8 reacts with three moles of hydrogen in the presence of a catalyst to yield an optically inactive product that cannot be resolved.X also exhibits IR absorption at approximately 3300 cm-1.Which is a possible structure for X?

What is the major product of the following reaction sequence?

An alkene with the molecular formula C8H16 undergoes ozonolysis to yield a mixture of (CH3)2C=O and (CH3)3CCHO.The alkene is:

What product would result from the following reaction?

Which of the following would be produced upon ozonolysis of camphene?

What is the major product of the following reaction sequence?

Even when one or more stereogenic centers are produced as the result of an addition reaction to an alkene,the product is always formed as a racemic mixture.Why is that?

Which reaction would yield a racemic product?

Which reaction sequence would convert cis-2-butene to trans-2-butene?

What is the product(s)formed by treating 3,3 dimethylcyclopentene with H3O+ and heating?

What is the major product for the following reaction?

What is the major product for the following reaction?

What is the major product of the following reaction sequence?

What is the major product for the following reaction?

What would be the major product of the following reaction?

An optically active compound,Y,with the molecular formula C7H12 gives a positive test with cold dilute KMnO4 and shows IR absorption at about 3300 cm-1.On catalytic hydrogenation,Y yields Z(C7H16)and Z is also optically active.Which is a possible structure for Y?

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

The Basics

Families of Carbon

Acids and Bases

Nomenclature and Conformations of Alkanes and Cycloalkanes

Stereochemistry

Nucleophilic Reactions

Alkenes and Alkynes I

Nuclear Magnetic Resonance and Mass Spectrometry

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Reactions at the Α Carbon of Carbonyl Compounds

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

Amines

Transition Metal Complexes

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

An alkene with the molecular formula C₈H₁₆undergoes ozonolysis to yield a mixture of (CH₃)₂C=O and (CH₃)₃CCHO.The alkene is:

An optically active compound,Y,with the molecular formula C₇H₁₂gives a positive test with cold dilute KMnO₄ and shows IR absorption at about 3300 cm^-1.On catalytic hydrogenation,Y yields Z(C₇H₁₆)and Z is also optically active.Which is a possible structure for Y?