Question 1

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

Accepted Answer

1. (CH₃)₃SiCl / (CH₃CH₂)

Question 2

Which of the following compounds is consistent with the following proton decoupled 13C NMR spectrum?

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 3

Predict the product(s) for the following reaction sequence.

Accepted Answer

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

Question 4

What is the IUPAC name for isobutyl alcohol?

Accepted Answer

A)  2-methyl-1-propanol 
B)  2-methyl-1-butanol 
C)  1-methyl-1-propanol 
D)  1,1-dimethyl-1-ethanol 
E)  3-methyl-1-propanol 
A)  2-methyl-1-propanol 
B)  2-methyl-1-butanol 
C)  1-methyl-1-propanol 
D)  1,1-dimethyl-1-ethanol 
E)  3-methyl-1-propanol

Question 5

Predict the product for the following reaction sequence.

Accepted Answer

A)  2,4-heptanediol 
B)  1,4-heptanediol 
C)  2,5-octanediol 
D)  1,5-octanediol 
E)  none of these 
A)  2,4-heptanediol 
B)  1,4-heptanediol 
C)  2,5-octanediol 
D)  1,5-octanediol 
E)  none of these

Question 6

Predict the product 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 reagent(s) necessary to convert cyclohexanol to cyclohexane..

Accepted Answer

1. H₂SO₄, heat 2. H₂/Pd

Question 8

Predict the product when cis-3-methylcyclopentanol is treated with TsCl/pyridine, followed by sodium bromide.

Accepted Answer

A)  trans-1-bromo-3-methylcyclopentane 
B)  cis-1-bromo-3-methylcyclopentane 
C)  1-methylcyclopentene 
D)  2-methylcyclopentene 
E)  3-methylcyclopentene 
A)  trans-1-bromo-3-methylcyclopentane 
B)  cis-1-bromo-3-methylcyclopentane 
C)  1-methylcyclopentene 
D)  2-methylcyclopentene 
E)  3-methylcyclopentene

Question 9

What is the IUPAC name for the following compound?

Accepted Answer

The answer of What is the IUPAC name for the...

Question 10

Identify the alcohol in alcoholic drinks.

Accepted Answer

A)  methanol 
B)  2-propanol 
C)  ethanol 
D)  1-butanol 
E)  1-propanol 
A)  methanol 
B)  2-propanol 
C)  ethanol 
D)  1-butanol 
E)  1-propanol

Question 11

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 12

Predict the product for the following reaction.

Accepted Answer

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

Question 13

Provide the structure for the final product (E), in 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 14

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

A)  NaOH/H2O 
B)  1. NaOCH3, 2. H3O+ 
C)  1. (CH3)3COK, 2. BH3•THF, 3. H2O2/NaOH/H2O 
D)  1. (CH3)3COK, 2. H3O+ 
E)  B & D 
A)  NaOH/H2O 
B)  1. NaOCH3, 2. H3O+ 
C)  1. (CH3)3COK, 2. BH3•THF, 3. H2O2/NaOH/H2O 
D)  1. (CH3)3COK, 2. H3O+ 
E)  B & D

Question 15

Predict the product for the following reaction.

Accepted Answer

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

Question 16

A compound with a molecular formula C9H12O has the following 1H NMR spectrum. Which of the following structures is consistent with this spectrum?

Accepted Answer

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

Question 17

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

The answer of Provide the reagents necessary to carry out...

Question 18

Predict the product for the following reaction.

Accepted Answer

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

Question 19

What is the IUPAC name for the following compound?

Accepted Answer

3,5-dimeth

Question 20

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

A)  KMnO4/NaOH/H2O 
B)  Na2Cr2O7/H2SO4/H2O 
C)  PCC/CH2Cl2 
D)  Br2, CCl4 
E)  None of these 
A)  KMnO4/NaOH/H2O 
B)  Na2Cr2O7/H2SO4/H2O 
C)  PCC/CH2Cl2 
D)  Br2, CCl4 
E)  None of these

Exam 12: Alcohols and Phenols

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

Which of the following compounds is consistent with the following proton decoupled 13C NMR spectrum?

Predict the product(s) for the following reaction sequence.

What is the IUPAC name for isobutyl alcohol?

Predict the product for the following reaction sequence.

Predict the product for the following reaction. .

Provide the reagent(s) necessary to convert cyclohexanol to cyclohexane..

Predict the product when cis-3-methylcyclopentanol is treated with TsCl/pyridine, followed by sodium bromide.

What is the IUPAC name for the following compound?

Identify the alcohol in alcoholic drinks.

Predict the product for the following reaction.

Predict the product for the following reaction.

Provide the structure for the final product (E), in the following reaction sequence.

Provide the reagents necessary to carry out the following conversion.

Predict the product for the following reaction.

A compound with a molecular formula C9H12O has the following 1H NMR spectrum. Which of the following structures is consistent with this spectrum?

Provide the reagents necessary to carry out the following conversion.

Predict the product for the following reaction.

What is the IUPAC name for the following compound?

Provide the reagents necessary to carry out the following conversion.

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

Which of the following compounds is consistent with the following proton decoupled ¹³C NMR spectrum?

A compound with a molecular formula C₉H₁₂O has the following ¹H NMR spectrum. Which of the following structures is consistent with this spectrum?