Question 1

Which of the following statements correctly describes the oxidation of alcohols?

Accepted Answer

A secondary alcohol is oxidized to a ketone, and a primary alcohol is oxidized to an aldehyde, which can further oxidize to a carboxylic acid.

Question 2

Which reagent can be used to oxidize an aldehyde to a carboxylic acid?

Accepted Answer

$$\mathrm{K_2Cr_2O_7}/\mathrm{H^+}$$

Question 3

Which of the following best explains why the boiling points of aldehydes and ketones are higher than those of alkanes but lower than those of alcohols?

Accepted Answer

Aldehydes and ketones have dipole-dipole interactions due to the carbonyl group, but cannot hydrogen bond with each other like alcohols.

Question 4

Which of the following compounds is a reducing sugar?

Accepted Answer

Maltose

Question 5

A carbohydrate with the molecular formula $$\mathrm{C_6H_{12}O_6$}$$ and a carbonyl group on carbon 2 is best classified as:

Accepted Answer

A ketohexose

Question 6

Which of the following statements about cellulose is correct?

Accepted Answer

Humans cannot digest cellulose because they lack the enzyme to hydrolyze $$\beta (1 \rightarrow 4)$$ glycosidic bonds.

Question 7

Which of the following best describes a chiral carbon?

Accepted Answer

A carbon atom bonded to four different groups, resulting in non-superimposable mirror images.

Question 8

Which of the following is true regarding the Fisher projection of D-glucose?

Accepted Answer

The OH group on the last chiral carbon is on the right.

Question 9

Which of the following statements about the oxidation of thiols is correct?

Accepted Answer

Oxidation of a thiol forms a disulfide bond.

Question 10

Which of the following best describes the glycosidic linkage in lactose?

Accepted Answer

$$\beta (1 \rightarrow 4)$$

Question 11

A student is given a sample of an unknown carbohydrate. It is found to be soluble in water, gives a positive Benedict's test, and is hydrolyzed to yield only glucose. Which carbohydrate is it most likely to be?

Accepted Answer

Maltose

Question 12

Which of the following is NOT a correct statement about the nomenclature of aldehydes?

Accepted Answer

The carbonyl group in an aldehyde can be located on any carbon in the chain.

Question 13

Which of the following statements about the reduction of carbonyl compounds is correct?

Accepted Answer

Aldehydes are reduced to primary alcohols, and ketones are reduced to secondary alcohols.

Question 14

Which of the following best describes the structure of amylopectin?

Accepted Answer

A branched polymer of glucose with $$\alpha (1 \rightarrow 4)$$ linkages and some $$\alpha (1 \rightarrow 6)$$ branches.

Question 15

Which of the following is true about the solubility of aldehydes and ketones in water?

Accepted Answer

Aldehydes and ketones with one to four carbons are soluble in water.

Question 16

Which of the following statements about sucrose is correct?

Accepted Answer

Sucrose is composed of glucose and fructose linked by an $$\alpha,\beta (1 \rightarrow 2)$$ glycosidic bond.

Question 17

Which of the following best describes the difference between glucose and galactose?

Accepted Answer

They differ at carbon 4, where the orientation of the OH and H groups is switched.

Question 18

Which of the following is true regarding the Haworth structure of β-D-glucose?

Accepted Answer

The OH group on the anomeric carbon (carbon 1) is pointing up.

Question 19

Which of the following best explains why humans cannot digest cellulose?

Accepted Answer

Humans lack the enzyme to hydrolyze $$\beta (1 \rightarrow 4)$$ glycosidic bonds.

Alcohols, Thiols, Phenols, Ethers, Aldehydes, Ketones, and Carbohydrates: Study Guide

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