Question 1

Which of the following statements best describes the structure of the carbonyl group in aldehydes and ketones?

Accepted Answer

The carbonyl carbon is sp\^2 hybridized with bond angles of 120\degree, and the C=O bond is polarized due to the electronegativity of oxygen.

Question 2

Which of the following is the correct IUPAC name for the compound CH\_3CH\_2CH\_2CH\_2CHO?

Accepted Answer

Pentanal

Question 3

A ketone is present as a substituent on a higher priority main carbon chain. How is it named according to IUPAC rules?

Accepted Answer

By using the prefix 'oxo-' before the parent name.

Question 4

Which of the following physical properties is most influenced by the ability of aldehydes and ketones to accept hydrogen bonds from water?

Accepted Answer

Water solubility

Question 5

Which reagent would selectively reduce a nitrile to an aldehyde?

Accepted Answer

1) DIBAL-H, -78\degree C; 2) H\_2O

Question 6

Which synthetic route would best convert a carboxylic acid to an aldehyde, avoiding over-reduction to a primary alcohol?

Accepted Answer

Convert the acid to an acid chloride, then reduce with LiAlH(OtBu)\_3

Question 7

Which of the following reactions is a general route to aldehydes from alkynes?

Accepted Answer

Hydroboration followed by oxidation: $$1) \mathrm{Sia}_2\mathrm{BH}, 2) \mathrm{H}_2\mathrm{O}_2, \mathrm{NaOH}$$

Question 8

What is the product of the following reaction sequence? $$\mathrm{PhCH}_2\mathrm{CN} \xrightarrow{1) \mathrm{MgBr}, 2) \mathrm{H}_2\mathrm{O}}$$

Accepted Answer

Benzyl phenyl ketone

Question 9

Which of the following statements about the Friedel-Crafts acylation is correct?

Accepted Answer

It is a versatile route to aromatic aldehydes and ketones using acid chlorides and AlCl\_3.

Question 10

Which of the following best explains why aldehydes generally have higher boiling points than alkanes of similar molecular weight?

Accepted Answer

Aldehydes have a polar carbonyl group that increases dipole-dipole interactions.

Question 11

Which of the following is the correct product for the reaction: $$\mathrm{C}_6\mathrm{H}_5\mathrm{COCl} + \mathrm{LiAlH(OtBu)_3} \rightarrow$$ ?

Accepted Answer

Benzaldehyde

Question 12

Which reagent would you use to convert an ester to an aldehyde in good yield?

Accepted Answer

1) DIBAL-H, -78\degree C; 2) H\_2O

Question 13

Which of the following is a correct description of the Grignard reaction with nitriles?

Accepted Answer

It produces ketones after hydrolysis of the imine intermediate.

Question 14

Which of the following synthetic routes would best yield cyclopentanecarbaldehyde from ethyl cyclopentylacetate?

Accepted Answer

1) DIBAL-H, -78\degree C; 2) H\_2O

Question 15

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

$$\mathrm{CH}_3\mathrm{CH}_2\mathrm{CH}_2\mathrm{COCH}_3$$

Accepted Answer

2-pentanone

Question 16

Which of the following statements about the reactivity of organolithium reagents with carboxylate salts is correct?

Accepted Answer

Organolithium reagents react with carboxylate salts to form ketones.

Question 17

Which of the following is a plausible product for the reaction: $$\mathrm{CH}_3\mathrm{CH}_2\mathrm{CH}_2\mathrm{CN} \xrightarrow{1) \mathrm{DIBAL-H}, 2) \mathrm{H}_2\mathrm{O}}$$?

Accepted Answer

Butanal

Question 18

Which of the following best describes the selectivity of lithium tri-tert-butoxyaluminum hydride (LiAlH(OtBu)\_3) in organic synthesis?

Accepted Answer

It reduces acid chlorides to aldehydes without reducing the aldehyde further.

Question 19

Which of the following is the correct product for the reaction: $$\mathrm{CH}_3\mathrm{CH}_2\mathrm{COCl} + \mathrm{(C_2H_5)_2CuLi} \rightarrow$$ ?

Accepted Answer

Butanone

Aldehydes and Ketones: Structure, Nomenclature, Properties, and Synthesis

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