Question 1

Which of the following statements best explains why aldehydes are generally more reactive toward nucleophilic addition than ketones?

Accepted Answer

Aldehydes are less sterically hindered and have only one alkyl group attached to the carbonyl carbon, making them more susceptible to nucleophilic attack.

Question 2

What is the hybridization and geometry of the carbon atom in a carbonyl group?

Accepted Answer

sp\^2 hybridized, trigonal planar geometry

Question 3

Which of the following correctly describes the partial charges in a carbonyl group?

Accepted Answer

The carbon is partially positive ($$\delta^+) $$and the oxygen is partially negative ($$\delta^-).$$

Question 4

Which reagent would you use to selectively reduce an aldehyde to a primary alcohol without affecting an ester group in the same molecule?

Accepted Answer

Sodium borohydride ($$\mathrm{$$NaBH_4$$})$$

Question 5

A Grignard reagent ($$\mathrm{RMgBr}) $$reacts with formaldehyde ($$\mathrm{H_2C=O}) $$followed by aqueous workup. What is the major organic product?

Accepted Answer

A primary alcohol

Question 6

Which of the following best explains why organometallic reagents such as Grignard reagents must be prepared and used in aprotic solvents like diethyl ether?

Accepted Answer

They are strong bases and will react with protic solvents, destroying the reagent.

Question 7

Which of the following is the correct product when a Gilman reagent ($$\mathrm{R_2CuLi}) $$reacts with an acid chloride ($$\mathrm{R'COCl}$$)?

Accepted Answer

A ketone ($$\mathrm{R'COR})$$

Question 8

What is the main difference in the reactivity of $$\mathrm{$$LiAlH_4$$}$$ and $$\mathrm{$$NaBH_4$$} as $$reducing agents?

Accepted Answer

$$\mathrm{$$LiAlH_4$$} is $$more reactive and can reduce a wider range of carbonyl compounds, including esters and carboxylic acids.

Question 9

Which of the following best describes the product of a Wittig reaction between benzaldehyde and methyltriphenylphosphonium ylide?

Accepted Answer

Styrene ($$\mathrm{C_6H_5CH=CH_2$})$$

Question 10

A student wants to perform a Grignard addition to a carbonyl compound that also contains an alcohol group. What is the best strategy to ensure the Grignard reagent reacts only with the carbonyl?

Accepted Answer

Protect the alcohol group with a protecting group such as a silyl ether before adding the Grignard reagent.

Question 11

Which of the following carbonyl compounds is most reactive toward nucleophilic addition?

Accepted Answer

Formaldehyde ($$\mathrm{H_2C=O})$$

Question 12

Which of the following best describes the mechanism of nucleophilic addition to a carbonyl group?

Accepted Answer

The nucleophile attacks the carbonyl carbon, forming a tetrahedral intermediate.

Question 13

Which of the following is a correct statement about the reaction of organometallic reagents with epoxides?

Accepted Answer

The nucleophile attacks the less hindered (less substituted) carbon of the epoxide.

Question 14

A chemist wants to synthesize 2-phenyl-2-propanol from acetone. Which reagent should be used?

Accepted Answer

Phenylmagnesium bromide ($$\mathrm{C_6H_5MgBr})$$

Question 15

Which of the following best explains why the carbonyl carbon is susceptible to nucleophilic attack?

Accepted Answer

It is partially positive due to the electronegativity of the oxygen atom.

Question 16

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

$$\mathrm{CH_3CH_2COCH_2CH_3}$$

Accepted Answer

2-pentanone

Question 17

Which of the following statements about the Wittig reaction is correct?

Accepted Answer

It converts a carbonyl group into an alkene using a phosphonium ylide.

Question 18

Which of the following is a correct statement about the use of protecting groups in carbonyl chemistry?

Accepted Answer

Protecting groups are used to temporarily mask reactive functional groups to prevent unwanted reactions.

Question 19

Which of the following best describes the product of the reaction between a Grignard reagent and carbon dioxide ($$\mathrm{CO_2$}) $$followed by acid workup?

Accepted Answer

A carboxylic acid

Organometallics and Reactions of Aldehydes & Ketones: Structure, Reactivity, and Nomenclature

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