Organic Chemistry Reactions: Oxidation & Alcohol Transformations

Posted on Jul 5, 2025 in Chemistry

  1. Incorrect

    Question 1

    Which one of the following statements does not describe an oxidation?

    Correct Answer: Addition of a hydride ion

  2. Incorrect

    Question 2

    Which sequence shows the correct ordering with regard to an increase in the oxidation state for the oxidation of methanol?

    Correct Answer: Methanol < Formaldehyde < Formic Acid < Carbon Dioxide

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    Question 3

    Which is the correct formula for sodium dichromate?

    Correct Answer: Na2Cr2O7

  4. Correct

    Question 4

    Oxidations with chromic acid can easily be monitored since the oxidized and reduced forms of chromium have different colors. Which color change accompanies the reduction of chromate to chromic ion?

    Your Answer: Orange to deep green

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    Question 5

    For which of the following oxidation reactions does one need to use pyridinium chlorochromate (PCC)?

    Correct Answer: Ethanol to acetaldehyde

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    Question 6

    The “Jones Reagent” is special in that it is added to a substrate dissolved in an organic solvent. Which organic solvent is frequently used for such oxidation with the “Jones Reagent”?

    Correct Answer: Acetone

  7. Correct

    Question 7

    Which reagents are used in the “Swern Oxidation”?

    Your Answer: (CH3)2SO and Cl-CO-CO-Cl

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    Question 8

    A tosylate ester, TsOR, is formally the product of condensation of an alcohol with para-toluenesulfonic acid, TsOH. How is a tosyl ester actually made?

    Correct Answer: A reaction of para-toluenesulfonic acid chloride, TsCl, with alcohol using pyridine as a proton acceptor.

  9. Incorrect

    Question 9

    Via tosylates, alcohols can be converted into a variety of other useful classes of compounds. Identify the nucleophile that is least suitable for this type of process.

    Correct Answer: Alcohol to make ethers

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    Question 10

    Which combination of chemicals is known as the “Lucas Reagent”?

    Correct Answer: HCl, ZnCl2

  11. Incorrect

    Question 11

    How quickly would a separate layer form if tert-butanol was submitted to the Lucas test?

    Correct Answer: Less than 1 minute

  12. Incorrect

    Question 12

    In the reaction of phosphorus pentachloride with an alcohol to form an alkyl chloride, what phosphorus-containing compound is generated?

    Your Answer: H3PO3

    Correct Answer: OPCl3

    Feedback: This is the product from PCl3.

  13. Incorrect

    Question 13

    What is the molecular formula of thionyl chloride?

    Correct Answer: OSCl2

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    Question 14

    Suppose (R)-2-butanol is treated with thionyl chloride to give 2-chlorobutane. What is the stereochemical outcome of this reaction?

    Correct Answer: Retention

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    Question 15

    In the course of the reaction with alcohol, thionyl chloride is converted into sulfur dioxide. How many lone pairs are there on all atoms in the best Lewis structure of sulfur dioxide?

    Correct Answer: 5

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    Question 16

    What reagent allows for the dehydration of alcohols under mild basic conditions?

    Correct Answer: OPCl3 and pyridine

  17. Correct

    Question 17

    What is the key step of the generic pinacol rearrangement?

    Your Answer: Methyl shift in a carbocation

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    Question 18

    1,2-Dimethylcyclopentene is oxidized with osmium tetroxide and hydrogen peroxide, and then treated with periodic acid. What product is formed?

    Correct Answer: 2,6-Heptanedione

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    Question 19

    Consider the Fischer esterification of methanol with formic acid. Which statement does not apply?

    Correct Answer: Adding more mineral acid shifts the equilibrium toward more ester formation.

  20. Correct

    Question 20

    What is nitroglycerin? Glycerin is 1,2,3-propanetriol.

    Your Answer: The trinitrate of glycerin

  21. Incorrect

    Question 21

    Phosphoric acid can form mono-, di-, and triesters. Diesters of phosphoric acid are part of the backbone of RNA and DNA. Identify the molecular formula of the dimethyl ester of phosphoric acid.

    Correct Answer: O=P(OH)(OMe)2