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 are required 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

Formation of enolate ion from 6-methylcyclohexanone

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: benzene $$\xrightarrow{Br_2$, $$FeBr_3$$} A$$ $$\xrightarrow{Mg, ether} B$$ $$\xrightarrow{CO_2$, H_2O} C$$, what is compound C?

Accepted Answer

Benzoic acid

Question 8

Which reagent is used to oxidize a primary alcohol to an aldehyde in the laboratory?

Accepted Answer

PCC (Pyridinium chlorochromate)

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.

Question 11

What is the major product when benzyl bromide is treated with aqueous NaOH?

Accepted Answer

Benzyl alcohol

Question 12

Which step in the Aldol condensation mechanism is responsible for the formation of the carbon-carbon bond?

Accepted Answer

Nucleophilic attack of the enolate ion on the carbonyl carbon of the aldehyde

Question 13

Which of the following statements about the use of Grignard reagents in organic synthesis is correct?

Accepted Answer

Grignard reagents react with carbon dioxide to form carboxylic acids after hydrolysis.

Question 14

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.

Organic Chemistry Study Guidance: Bases, Acidity, Aldol Condensation, and Compound Identification

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