Question 1

Rank the following alcohols in decreasing order of acidity.

Accepted Answer

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

Question 2

Identify the characteristics of the hydroboration-oxidation of an alkene.

Accepted Answer

A)  Markovnikov, with rearrangement possible 
B)  Markovnikov, with no rearrangement possible 
C)  anti-Markovnikov, with rearrangement possible 
D)  anti-Markovnikov, with no rearrangement possible 
A)  Markovnikov, with rearrangement possible 
B)  Markovnikov, with no rearrangement possible 
C)  anti-Markovnikov, with rearrangement possible 
D)  anti-Markovnikov, with no rearrangement possible

Question 3

Predict the product for the following reaction.

Accepted Answer

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

Question 4

Provide the reagent(s) necessary to carry out the following conversion.

Accepted Answer

1. excess

Question 5

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

A)  KMnO4, NaOH,H2O,cold 
B)  KMnO4, H3O+, 75oC 
C)  H2SO4, heat 
D)  1. mCPBA 2. H3O+ 
E)  none of these 
A)  KMnO4, NaOH,H2O,cold 
B)  KMnO4, H3O+, 75oC 
C)  H2SO4, heat 
D)  1. mCPBA 2. H3O+ 
E)  none of these

Question 6

Provide the reactant (A) for 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

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

1. NaOH
2.

Question 8

Provide the structure for each product (A-C) in the following reaction sequence.

Accepted Answer

The answer of Provide the structure for each product (A-C)...

Question 9

Using a Grignard reaction, show how you could prepare the following alcohol.

Accepted Answer

The answer of Using a Grignard reaction, show how you...

Question 10

Provide the reagent(s) necessary to prepare 1-isopropylcyclopentanol using a Grignard reaction.

Accepted Answer

The answer of Provide the reagent(s) necessary to prepare 1-isopropylcyclopentanol...

Question 11

Predict the product for the following reaction.

Accepted Answer

The answer of Predict the product for the following reaction....

Question 12

Predict the 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 13

Predict the product for the following reaction sequence.

Accepted Answer

The answer of Predict the product for the following reaction...

Question 14

Predict the product for the following reaction.

Accepted Answer

The answer of Predict the product for the following reaction....

Question 15

What is the correct structure for 2,2-dibromo-1-methylcyclohexanol?

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 for the following compound?

Accepted Answer

(R)-3-ethy

Question 17

What is the IUPAC name for the following compound?

Accepted Answer

A)  1-isopropyl-4-cyclopentanol 
B)  3-isopropylcyclopentanol 
C)  1-isopropyl-3-cyclopentanol 
D)  1-isopropyl-4-hydroxycyclopentane 
E)  None of these 
A)  1-isopropyl-4-cyclopentanol 
B)  3-isopropylcyclopentanol 
C)  1-isopropyl-3-cyclopentanol 
D)  1-isopropyl-4-hydroxycyclopentane 
E)  None of these

Question 18

Provide the structure for (2R,3S) -2-bromo-1,3-pentanediol.

Accepted Answer

The answer of Provide the structure for (2R,3S) -2-bromo-1,3-pentanediol....

Question 19

Predict the product for the following reaction.

Accepted Answer

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

Question 20

For the following conversion, identify if the starting material has been oxidized, reduced or neither.

Accepted Answer

A)  reduced 
B)  oxidized 
C)  neither 
D)  A & B 
A)  reduced 
B)  oxidized 
C)  neither 
D)  A & B

Exam 12: Alcohols and Phenols

Rank the following alcohols in decreasing order of acidity.

Identify the characteristics of the hydroboration-oxidation of an alkene.

Predict the product for the following reaction.

Provide the reagent(s) necessary to carry out the following conversion.

Provide the reagents necessary to carry out the following conversion.

Provide the reactant (A) for the following reaction.

Provide the reagents necessary to carry out the following conversion.

Provide the structure for each product (A-C) in the following reaction sequence.

Using a Grignard reaction, show how you could prepare the following alcohol.

Provide the reagent(s) necessary to prepare 1-isopropylcyclopentanol using a Grignard reaction.

Predict the product for the following reaction.

Predict the product, for the following reaction sequence.

Predict the product for the following reaction sequence.

Predict the product for the following reaction.

What is the correct structure for 2,2-dibromo-1-methylcyclohexanol?

What is the IUPAC name for the following compound?

What is the IUPAC name for the following compound?

Provide the structure for (2R,3S) -2-bromo-1,3-pentanediol.

Predict the product for the following reaction.

For the following conversion, identify if the starting material has been oxidized, reduced or neither.

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

Addition Reactions of Alkenes

Alkynes

Radical Reactions

Synthesis

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