Question 1

Which statement best explains why the C=O bond in carbonyl compounds is shorter and stronger than the C=C bond in alkenes?

Accepted Answer

Because the C=O bond is polarized due to the electronegativity difference between carbon and oxygen, resulting in stronger and shorter bonding.

Question 2

What is the correct IUPAC name for the following compound: $$\mathrm{CH_3CH_2CH_2COCH_3}$$?

Accepted Answer

2-pentanone

Question 3

Which of the following statements about the physical properties of aldehydes and ketones is TRUE?

Accepted Answer

Aldehydes and ketones have lower boiling points than analogous alcohols due to lack of hydrogen bonding between their molecules.

Question 4

Which reagent and condition is used in the Rosenmund reduction to convert an acid chloride to an aldehyde?

Accepted Answer

$$\mathrm{H_2$}$$ and $$\mathrm{Pd/$$BaSO_4$$}$$

Question 5

During ozonolysis of 2-butene ($$\mathrm{CH_3CH=$$CHCH_3$$}) $$followed by reductive workup with Zn/H$$^+$$, what are the major organic products?

Accepted Answer

Two molecules of acetaldehyde ($$\mathrm{CH_3CHO})$$

Question 6

Which test can be used to distinguish between an aldehyde and a ketone, and what is the expected result for an aldehyde?

Accepted Answer

Tollen's test; formation of a silver mirror

Question 7

Which of the following is the correct reaction for the oxidation of an aldehyde with Tollen's reagent?

Accepted Answer

$$2Ag(NH_3$)_2^+ + RCHO + 3OH^- \rightarrow 2Ag + RCOO^- + 4NH_3 + 2H_2O$$

Question 8

Why do aldehydes generally react faster than ketones in nucleophilic addition reactions?

Accepted Answer

Aldehydes have less steric hindrance and greater partial positive charge on the carbonyl carbon.

Question 9

What is the product when an aldehyde reacts with one equivalent of alcohol under acidic conditions?

Accepted Answer

Hemiacetal

Question 10

Which of the following is the correct sequence for the formation of an acetal from an aldehyde?

Accepted Answer

Aldehyde + 2 ROH $$\xrightarrow{H^+}$$ Acetal + H$$_2O$$

Question 11

Which of the following statements about Fehling's and Benedict's tests is correct?

Accepted Answer

Both tests use Cu$$^{2+}$$ ions as oxidants and produce a brick red precipitate of Cu$$_2O $$when aldehydes are present.

Question 12

What is the product when a ketone reacts with HCN in the presence of base?

Accepted Answer

Cyanohydrin

Question 13

Which of the following is a correct statement about the solubility of aldehydes and ketones in water?

Accepted Answer

They are more soluble than alkanes but less soluble than alcohols.

Question 14

Which of the following reactions is used to synthesize aromatic ketones?

Accepted Answer

Friedel-Crafts acylation

Question 15

What is the major product when benzene reacts with acetyl chloride ($$\mathrm{CH_3COCl}) in $$the presence of $$\mathrm{$$AlCl_3$$}$$?

Accepted Answer

Acetophenone ($$\mathrm{C_6H_5COCH_3})$$

Question 16

Which of the following is the correct product when a Grignard reagent ($$\mathrm{RMgX}) $$reacts with a ketone followed by hydrolysis?

Accepted Answer

A tertiary alcohol

Question 17

Which of the following is the correct IUPAC name for the compound shown below?

$$\mathrm{CH_3CH_2CH_2CH_2COCH_2CH_3}$$

Accepted Answer

3-heptanone

Question 18

Which of the following statements about the nucleophilic addition of water to a carbonyl compound is correct?

Accepted Answer

The product is a hydrate (gem-diol) formed by the addition of water to the carbonyl group.

Question 19

Which of the following is the correct product when an aldehyde reacts with sodium bisulfite ($$\mathrm{$$NaHSO_3$$}$$)?

Accepted Answer

A bisulfite addition compound (alkylsulfonate)

Carbonyl Compounds: Aldehydes and Ketones I – Structure, Properties, Synthesis, and Reactions

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