Question 1

Which of the following compounds is the stronger base: $$\mathrm{ClCH_2CH_2NH_2} or$$ $$\mathrm{CH_3CH_2NH_2}$$? Explain your choice based on electronic effects.

Accepted Answer

$$\mathrm{CH_3CH_2NH_2}$$, because the chlorine atom in $$\mathrm{ClCH_2CH_2NH_2}$$ withdraws electron density, making the nitrogen less basic.

Question 2

Rank the following compounds in order of increasing acidity: $$\mathrm{C_6H_5CO_2H}$$, $$\mathrm{CH_3CO_2H}$$, $$\mathrm{C_6H_5CH_2CO_2H}.$$

Accepted Answer

$$\mathrm{CH_3CO_2H} \u003c \mathrm{C_6H_5CH_2CO_2H} \u003c \mathrm{C_6H_5CO_2H}$$

Question 3

Which two carbonyl compounds can be used to synthesize $$(E)-2-$$benzylidene-6-methylcyclohexanone via Aldol condensation?

Accepted Answer

Benzaldehyde and 6-methylcyclohexanone

Question 4

In the base-catalyzed Aldol condensation mechanism between benzaldehyde and 6-methylcyclohexanone, what is the first step?

Accepted Answer

Deprotonation of 6-methylcyclohexanone to form the enolate ion

Question 5

Which of the following best describes the role of NaOH in the Aldol condensation reaction?

Accepted Answer

It acts as a base to generate the enolate ion.

Question 6

What is the product of the reaction between benzene and bromine in the presence of $$\mathrm{$$FeBr_3$$}$$?

Accepted Answer

Bromobenzene

Question 7

In the sequence: $$\mathrm{C_6H_6} \xrightarrow{Br_2$, $$FeBr_3$$} A \xrightarrow{Mg, ether} B \xrightarrow{CO_2$, H_2O} C$$, what is compound C?

Accepted Answer

Benzoic acid ($$\mathrm{C_6H_5CO_2H})$$

Question 8

Which reagent is used to oxidize a primary alcohol to an aldehyde without further oxidation to a carboxylic acid?

Accepted Answer

Pyridinium chlorochromate (PCC)

Question 9

Which of the following best explains why $$\mathrm{C_6H_5CO_2H} is $$more acidic than $$\mathrm{CH_3CO_2H}$$?

Accepted Answer

The phenyl group stabilizes the carboxylate ion by resonance.

Question 10

Which of the following is a real-world application of pheromones such as methyl geranate in agriculture?

Accepted Answer

They are used as attractants to control pest populations in integrated pest management.

Question 11

Which of the following statements about Aldol condensation is correct?

Accepted Answer

It involves the formation of a carbon-carbon bond between the alpha carbon of one carbonyl compound and the carbonyl carbon of another.

Question 12

What is the major product when benzyl bromide is treated with magnesium in dry ether followed by carbon dioxide and acid workup?

Accepted Answer

Phenylacetic acid

Question 13

Which of the following best describes the effect of an electron-withdrawing group on the acidity of a carboxylic acid?

Accepted Answer

It increases the acidity by stabilizing the conjugate base.

Question 14

Which of the following is the correct order of reactivity towards nucleophilic addition: aldehydes, ketones, esters?

Accepted Answer

Aldehydes \u003e ketones \u003e esters

Question 15

Which of the following is a key intermediate in the Grignard reaction with carbon dioxide?

Accepted Answer

Carboxylate anion

Organic Chemistry: Acidity, Basicity, Aldol Condensation, and Reaction Mechanisms

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