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Test: Alcohols and Phenols - MCAT MCQ


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10 Questions MCQ Test Organic Chemistry for MCAT - Test: Alcohols and Phenols

Test: Alcohols and Phenols for MCAT 2024 is part of Organic Chemistry for MCAT preparation. The Test: Alcohols and Phenols questions and answers have been prepared according to the MCAT exam syllabus.The Test: Alcohols and Phenols MCQs are made for MCAT 2024 Exam. Find important definitions, questions, notes, meanings, examples, exercises, MCQs and online tests for Test: Alcohols and Phenols below.
Solutions of Test: Alcohols and Phenols questions in English are available as part of our Organic Chemistry for MCAT for MCAT & Test: Alcohols and Phenols solutions in Hindi for Organic Chemistry for MCAT course. Download more important topics, notes, lectures and mock test series for MCAT Exam by signing up for free. Attempt Test: Alcohols and Phenols | 10 questions in 10 minutes | Mock test for MCAT preparation | Free important questions MCQ to study Organic Chemistry for MCAT for MCAT Exam | Download free PDF with solutions
Test: Alcohols and Phenols - Question 1
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Which of the following alcohols would have the lowest boiling point?

Detailed Solution for Test: Alcohols and Phenols - Question 1
  • Melting and boiling points depend on how strong the attractive forces are between individual atoms or molecules. The more energy it requires to pull various molecules away from one another, the higher the boiling point.
  • All of these molecules have a hydroxyl group, therefore another factor affecting intermolecular forces must be considered.
  • Ethanol is the shortest chain. It must lead to the lowest boiling point due to the lack of London dispersion forces
Test: Alcohols and Phenols - Question 2
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Which of the following alcohols would be most soluble in water?

Detailed Solution for Test: Alcohols and Phenols - Question 2
  • Like dissolves like. Water, with its hydrogen bonding would most likely associate with other molecules that can do the same.
  • Since all of the molecules have hydrogen bonding, another differentiating each choice must be considered.
  • The shorter the alkyl chain of alcohol, the less alkyl characteristic and the more soluble it is in water. Propanol has the shortest alkyl chain.
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Test: Alcohols and Phenols - Question 3
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What type of alcohol is 2-methyl-2-pentanol?

Detailed Solution for Test: Alcohols and Phenols - Question 3
  • According to the rules of nomenclature, this molecule has a five carbon chain with a methyl group and a hydroxyl group attached to the 2nd carbon.
  • The molecule looks like:
  • The carbon attached to the hydroxyl -OH group has three carbons attached to it. This is a tertiary alcohol.
Test: Alcohols and Phenols - Question 4
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Which of the following reactions will undergo an SN1 reaction?
Detailed Solution for Test: Alcohols and Phenols - Question 4
  • SN1 reactions typically have weak nucleophiles.
  • Large, branched electrophiles with great leaving groups lead to SN1 reactions.
  • Tertiary alkyl halides are large, branched electrophiles with great leaving groups. In addition, ethanol is a weak nucleophile. The reactants t-butyl bromide with ethanol are likely candidates to undergo SN1.
Test: Alcohols and Phenols - Question 5
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Which of the following reactions will undergo an SN2 reaction?
Detailed Solution for Test: Alcohols and Phenols - Question 5
  • SN2 reactions are preferred in reactants with no steric hindrance
  • A strong nucleophile along with a primary electrophile is indicative of SN2.
  • The reactants 1-bromobutane with KOH are likely candidates to undergo SN2.
Test: Alcohols and Phenols - Question 6
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Phenol can be a solid at room temperature while benzene is a liquid. What explains this difference?
Detailed Solution for Test: Alcohols and Phenols - Question 6
  • Differences in melting point is the result of a difference in intermolecular forces.
  • The only structural difference between phenol and benzene is the presence of the  –OH hydroxyl group in phenol.
  • The hydrogen bonding in phenol raises the melting point considerably due to its strong intermolecular force
Test: Alcohols and Phenols - Question 7
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Which of the following will convert this alcohol into a ketone?
Detailed Solution for Test: Alcohols and Phenols - Question 7
  • This alcohol is a secondary alcohol
  • An alcohol needs to be oxidized in order to to form a ketone. Reducing agents such as LiAlH4 and NaBH4 
  • O3 and Zn will only work on alkene double bonds.
  • Pyridinium Chlorochromate (PCC) will convert secondary alcohols into ketones.
Test: Alcohols and Phenols - Question 8
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Protecting an alcohol with tosyl chloride would likely have which of the following effects?
Detailed Solution for Test: Alcohols and Phenols - Question 8
  • The point of a protecting group is to protect the hydroxyl group and prevent it from reacting with a nucleophile.
  • The hydroxyl will lose its ability to donate its hydrogen ion and thus we would expect a decrease in the acidity of the molecule.
  • The solubility of a tosylate compound should decrease since the hydroxyl was smaller and could interact with water through hydrogen bonds.
Test: Alcohols and Phenols - Question 9
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Which of the following is a correct statement explaining why toluene is an aromatic molecule?
Detailed Solution for Test: Alcohols and Phenols - Question 9
  • Aromaticity follows Huckel's Rule, which states that the number of delocalized p-orbital electrons follows the rule 4n + 2, where n = 1 in the case of toluene.
  • Heteroatoms can replace carbon atoms in a ring and can still be aromatic such as in the case of pyridine.
  • All atoms involved in the ring have p-orbitals that overlap. This contributes to the molecule’s stability.
  • In order to have overlapping p-orbitals, it necessary for electron contributing atoms to be in the same orientation on the same plane.
Test: Alcohols and Phenols - Question 10
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The following biological molecule is exposed to NADH. What is the expected product?
Detailed Solution for Test: Alcohols and Phenols - Question 10
  • NADH is a molecule found in living systems that acts as a reducing agent.
  • When NADH is reacted with ubiquinone, the latter molecule’s ketones are reduced to secondary alcohols.
  • As a reducing agent, NADH will be oxidized during this reaction. The products should yield NAD+ and
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