MCAT Organic Chemistry Review

Alcohols

Practice Questions

1.    Alcohols have higher boiling points than their analogous hydrocarbons because:

1.    the oxygen atoms in alcohols have shorter bond lengths.

2.    hydrogen bonding is present in alcohols.

3.    alcohols are more acidic than their analogous hydrocarbons.

4.    alcohols can be oxidized to ketones.

2.    Tertiary alcohols are oxidized with difficulty because:

1.    there is no hydrogen attached to the carbon with the hydroxyl group.

2.    there is no hydrogen attached to the α-carbon of the carbonyl.

3.    tertiary alcohols contain hydroxyl groups with no polarization.

4.    they are relatively inert.

3.    The IUPAC name of this molecule is:

1.    ethane-1,2-diol.

2.    propane-1,2-diol.

3.    dimethanol.

4.    dipropanol.

4.    The IUPAC name of this molecule is:

1.    2-methylcyclohexanol.

2.    m-methylphenol.

3.    p-methylphenol.

4.    3-methylcyclohexanol.

5.    Which of the following correctly lists methanol, isobutyl alcohol, and propanol by decreasing boiling point?

1.    Methanol > isobutyl alcohol > propanol

2.    Isobutyl alcohol > methanol > propanol

3.    Isobutyl alcohol > propanol > methanol

4.    Methanol > propanol > isobutyl alcohol

6.    Which of the following correctly lists hexanol, phenol, and cyclohexanol by increasing acidity of the hydroxyl hydrogen?

1.    Phenol < hexanol < cyclohexanol

2.    Cyclohexanol < hexanol < phenol

3.    Cyclohexanol < phenol < hexanol

4.    Phenol < cyclohexanol < hexanol

7.    Which of the following will convert CH3CH2CH2OH to CH3CH2CHO?

1.    CrO3

2.    PCC

3.    K2Cr2O7

1.    I only

2.    II only

3.    I and III only

4.    I, II, and III

8.    Which of the following will convert cyclohexanol to cyclohexanone?

1.    Chromium trioxide

2.    Pyridinium chlorochromate

3.    Sodium dichromate

1.    I only

2.    II only

3.    I and III only

4.    I, II, and III

9.    Successfully converting 3-phenylpropanol to 3-phenylpropanoic acid by the Jones oxidation requires CrO3, acetone, and:

1.    dilute sulfuric acid.

2.    dilute sodium hydroxide.

3.    anhydrous conditions.

4.    high temperature.

10.Treating 2-methyl-1-propanol with methylsulfonyl chloride in base, followed by reaction with pyridinium chlorochromate, and a final step in strong acid, will give an end product of:

1.    2-methyl-1-propanol.

2.    2-methylpropanal.

3.    2-methylpropanoic acid.

4.    2-methyl-1-propane.

11.Reaction of 1-phenylethanone with ethylene glycol, also known as ethane-1,2-diol, in aqueous H2SO4 will result in the formation of:

1.    a ketal.

2.    a carboxylic acid.

3.    an aldehyde.

4.    a ketone.

12.Treatment of this molecule with CrO3 in aqueous H2SO4 in acetone will yield which of the following molecules?

1.    2-Phenylethanol

2.    Phenylacetaldehyde

3.    Phenylacetone

4.    2-Phenylethanoic acid

13.In order to convert phenols into hydroxyquinones, how many steps of oxidation or reduction are required?

1.    1 oxidation step

2.    2 oxidation steps

3.    1 reduction step

4.    2 reduction steps

14.The conversion of ubiquinone to ubiquinol requires what type of reaction?

1.    Condensation

2.    Oxidation

3.    Reduction

4.    Hydrolysis

15.Which of the following will convert a cyclic acetal to a carbonyl and a dialcohol?

1.    Aqueous acid

2.    LiAlH4

3.    CrO3

4.    Acetone

PRACTICE QUESTIONS