MCAT Organic Chemistry Practice Test 5: Alcohols

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

  • A. the oxygen atoms in alcohols have shorter bond lengths.
  • B. hydrogen bonding is present in alcohols.
  • C. alcohols are more acidic than their analogous hydrocarbons.
  • D. alcohols can be oxidized to ketones.

2. Tertiary alcohols are oxidized with difficulty because:

  • A. there is no hydrogen attached to the carbon with the hydroxyl group.
  • B. there is no hydrogen attached to the α-carbon of the carbonyl.
  • C. tertiary alcohols contain hydroxyl groups with no polarization.
  • D. they are relatively inert.

3. The IUPAC name of this molecule is:

  • A. ethane-1,2-diol.
  • B. propane-1,2-diol.
  • C. dimethanol.
  • D. dipropanol.

4. The IUPAC name of this molecule is:

  • A. 2-methylcyclohexanol.
  • B. m-methylphenol.
  • C. p-methylphenol.
  • D. 3-methylcyclohexanol.

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

  • A. Methanol > isobutyl alcohol > propanol
  • B. Isobutyl alcohol > methanol > propanol
  • C. Isobutyl alcohol > propanol > methanol
  • D. Methanol > propanol > isobutyl alcohol

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

  • A. Phenol < hexanol < cyclohexanol
  • B. Cyclohexanol < hexanol < phenol
  • C. Cyclohexanol < phenol < hexanol
  • D. Phenol < cyclohexanol < hexanol

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

I. CrO3

II. PCC

III. K2Cr2O7

  • A. I only
  • B. II only
  • C. I and III only
  • D. I, II, and III

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

I. Chromium trioxide

II. Pyridinium chlorochromate

III. Sodium dichromate

  • A. I only
  • B. II only
  • C. I and III only
  • D. I, II, and III

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

  • A. dilute sulfuric acid.
  • B. dilute sodium hydroxide.
  • C. anhydrous conditions.
  • D. 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:

  • A. 2-methyl-1-propanol.
  • B. 2-methylpropanal.
  • C. 2-methylpropanoic acid.
  • D. 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:

  • A. a ketal.
  • B. a carboxylic acid.
  • C. an aldehyde.
  • D. a ketone.

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

  • A. 2-Phenylethanol
  • B. Phenylacetaldehyde
  • C. Phenylacetone
  • D. 2-Phenylethanoic acid

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

  • A. 1 oxidation step
  • B. 2 oxidation steps
  • C. 1 reduction step
  • D. 2 reduction steps

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

  • A. Condensation
  • B. Oxidation
  • C. Reduction
  • D. Hydrolysis

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

  • A. Aqueous acid
  • B. LiAlH4
  • C. CrO3
  • D. Acetone