Question 1

Provide the expected major organic product from the reaction shown below. Provide a brief explanation of any regioselectivity the reaction is expected to produce.

Accepted Answer

@#IMG-DLM&_TB4454_00 The alcohol will be found at

Question 2

Draw Fischer projection (s) of the major product(s) of the reaction between (Z)-3-methyl-3-hexene and MCPBA, followed by aqueous acid.

Accepted Answer

@#IMG-DLM&_TB4454_00 The reaction takes

Question 3

What is the expected major product for the following reaction sequence?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of the above 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  None of the above

Question 4

Describe the regioselectivity and stereospecificity in the hydrohalogenation of an alkene.

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 5

Identify the major organic product generated from the reaction shown.

Accepted Answer

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

Question 6

Identify the expected 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 7

What is the expected 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 8

Starting with (2R,3R)-2-chloro-3,4-dimethylpentane, a) draw the expected major product for each step, including regiochemical and stereochemical details when needed. In addition, b) briefly explain the mechanistic rationale for each reaction.
i. t-BuOK/t-BuOH, heat
ii. MCPBA/CH2Cl2
iii. H3O+

Accepted Answer

@#IMG-DLM&_TB4454_00 Hofmann elimination occurs up

Question 9

What is the expected major product of 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 10

For the following equation a) identify the starting material with correct stereochemistry and b) provide a complete reaction mechanism, including stereochemistry, to account for the product shown.

Accepted Answer

@#IMG-DLM&_TB4454_00
 Step 1 involves the epoxidat

Question 11

What is a compound that does not have a double bond?

Accepted Answer

A)  allicin (garlic) 
B)  geraniol (roses) 
C)  cholesterol 
D)  limonene (oranges) 
E)  ammonia 
A)  allicin (garlic) 
B)  geraniol (roses) 
C)  cholesterol 
D)  limonene (oranges) 
E)  ammonia

Question 12

What is the expected major product of 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 13

Select the expected major product(s) of the following reaction.

Accepted Answer

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

Question 14

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

Accepted Answer

A)  0 
B)  1 
C)  2 
D)  3 
E)  4 
A)  0 
B)  1 
C)  2 
D)  3 
E)  4

Question 15

Identify the expected product(s) for the reaction shown below.

Accepted Answer

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

Question 16

What is the IUPAC name of the expected major product formed upon reaction of HCl with 3-methyl-1-butene?

Accepted Answer

A)  1-chloro-2-methylbutane 
B)  1-chloro-3-methylbutane 
C)  2-chloro-2-methylbutane 
D)  2-chloro-3-methylbutane 
E)  1-chloropentane 
A)  1-chloro-2-methylbutane 
B)  1-chloro-3-methylbutane 
C)  2-chloro-2-methylbutane 
D)  2-chloro-3-methylbutane 
E)  1-chloropentane

Question 17

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

Accepted Answer

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

Question 18

What is the expected major product of 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 19

Identify the compound that would react most rapidly with a dilute aqueous solution of H2SO4.

Accepted Answer

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

Question 20

For the following reaction sequence, which molecule is expected as the major product?

Accepted Answer

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

Exam 8: Addition Reactions of Alkenes

Provide the expected major organic product from the reaction shown below. Provide a brief explanation of any regioselectivity the reaction is expected to produce.

Draw Fischer projection (s) of the major product(s) of the reaction between (Z)-3-methyl-3-hexene and MCPBA, followed by aqueous acid.

What is the expected major product for the following reaction sequence?

Describe the regioselectivity and stereospecificity in the hydrohalogenation of an alkene.

Identify the major organic product generated from the reaction shown.

Identify the expected major product of the following reaction.

What is the expected major product for the following reaction sequence?

Starting with (2R,3R)-2-chloro-3,4-dimethylpentane, a) draw the expected major product for each step, including regiochemical and stereochemical details when needed. In addition, b) briefly explain the mechanistic rationale for each reaction. i. t-BuOK/t-BuOH, heat ii. MCPBA/CH2Cl2 iii. H3O+

What is the expected major product of the following reaction sequence?

For the following equation a) identify the starting material with correct stereochemistry and b) provide a complete reaction mechanism, including stereochemistry, to account for the product shown.

What is a compound that does not have a double bond?

What is the expected major product of the following reaction sequence?

Select the expected major product(s) of the following reaction.

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

Identify the expected product(s) for the reaction shown below.

What is the IUPAC name of the expected major product formed upon reaction of HCl with 3-methyl-1-butene?

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

What is the expected major product of the following reaction sequence?

Identify the compound that would react most rapidly with a dilute aqueous solution of H2SO4.

For the following reaction sequence, which molecule is expected as the major product?

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

Filters

Identify the compound that would react most rapidly with a dilute aqueous solution of H₂SO₄.