Question 1

Which of the following statements best describes the difference between oxidation and reduction in organic molecules?

Accepted Answer

Oxidation increases the number of C-O bonds and/or decreases the number of C-H bonds, while reduction increases the number of C-H bonds and/or decreases the number of C-O bonds.

Question 2

Which reagent would you use to selectively reduce an alkyne to a cis-alkene?

Accepted Answer

Lindlar catalyst ($$\mathrm{Pd/$$CaCO_3$$}$$ with quinoline)

Question 3

Which of the following best explains why catalytic hydrogenation of alkenes is considered a syn addition?

Accepted Answer

Both hydrogen atoms add to the same side of the double bond at the same time.

Question 4

Which of the following is the correct product when 2-butyne is treated with $$\mathrm{Na/NH_3$}$$?

Accepted Answer

trans-2-butene

Question 5

What is the major product when 1-butanol is oxidized with $$\mathrm{K_2Cr_2O_7} in $$acidic aqueous solution?

Accepted Answer

Butanoic acid

Question 6

Which of the following statements about the Sharpless epoxidation is correct?

Accepted Answer

It is highly enantioselective and can produce one enantiomer in excess using a chiral catalyst.

Question 7

Which of the following best describes the mechanism of dissolving metal reduction of alkynes?

Accepted Answer

Addition of two protons and two electrons in a stepwise fashion, forming a trans-alkene.

Question 8

Which of the following alcohols cannot be oxidized under normal laboratory conditions?

Accepted Answer

Tertiary alcohol

Question 9

What is the product of the reaction of cyclohexene with $$\mathrm{mCPBA}$$?

Accepted Answer

Cyclohexene oxide (an epoxide)

Question 10

Which of the following reagents would you use to achieve anti dihydroxylation of an alkene?

Accepted Answer

1. $$\mathrm{mCPBA}$$, 2. $$\mathrm{H_2O}$$

Question 11

Which of the following is a correct statement about the heat of hydrogenation of alkenes?

Accepted Answer

The less stable the alkene, the more energy is released during hydrogenation.

Question 12

Which of the following best describes the product(s) of ozonolysis of 2-methyl-2-butene followed by reductive workup ($$\mathrm{Zn/H_2O}$$)?

Accepted Answer

Acetone and formaldehyde

Question 13

Which of the following is the correct order of increasing oxidation state for the following carbon compounds: methane, methanol, formaldehyde, formic acid, carbon dioxide?

Accepted Answer

Methane \u003c methanol \u003c formaldehyde \u003c formic acid \u003c carbon dioxide

Question 14

Which of the following statements about the reduction of polar C-X $$\sigma$$ bonds with $$\mathrm{$$LiAlH_4$$} is $$correct?

Accepted Answer

$$\mathrm{$$LiAlH_4$$}$$ donates a hydride ion ($$\mathrm{H^-}) to $$the carbon atom bonded to X.

Question 15

Which of the following best describes the outcome when a terminal alkyne undergoes oxidative cleavage with $$\mathrm{O_3$}$$ and $$\mathrm{H_2O}$$?

Accepted Answer

A carboxylic acid and carbon dioxide

Question 16

Which of the following is a real-world application of Sharpless asymmetric epoxidation?

Accepted Answer

Synthesis of chiral insect pheromones

Question 17

Which of the following is the correct product when cyclohexene is treated with cold, dilute $$\mathrm{$$KMnO_4$$}$$?

Accepted Answer

cis-1,2-cyclohexanediol

Question 18

Which of the following best explains why tertiary alcohols do not undergo oxidation under normal laboratory conditions?

Accepted Answer

They lack a hydrogen atom on the carbon bearing the hydroxyl group.

Question 19

Which of the following is the correct sequence of steps for anti dihydroxylation of an alkene?

Accepted Answer

Epoxidation followed by ring opening with $$\mathrm{H_2O} or$$ $$\mathrm{OH^-}$$

Chapter 12: Oxidation and Reduction of Organic Molecules

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