Question 1

Which of the following compounds is expected to have the lowest pKa value based on the pKa scale provided in the image?

Accepted Answer

Hydrochloric acid ($$ \mathrm{HCl} )$$

Question 2

Arrange the following compounds in order of increasing acidity: $$ \mathrm{CH_3CH_2OH} $$, $$ \mathrm{CH_3COOH} $$, $$ \mathrm{H_2O} .$$

Accepted Answer

$$ \mathrm{CH_3CH_2OH} \u003c \mathrm{H_2O} \u003c \mathrm{CH_3COOH} $$

Question 3

Which of the following statements best explains why $$ \mathrm{F^-}  is a $$weaker base than $$ \mathrm{I^-} $$?

Accepted Answer

Fluorine is more electronegative, stabilizing the negative charge better.

Question 4

Which compound would react fastest in an SN2 reaction with KOH: $$ \mathrm{CH_3Br} $$, $$ \mathrm{(CH_3)_2CHBr} $$, $$ \mathrm{(CH_3)_3CBr} $$, or $$ \mathrm{C_6H_5CH_2Br} $$?

Accepted Answer

$$ \mathrm{C_6H_5CH_2Br} $$

Question 5

Which of the following best describes the trend in acidity for the following functional groups: carboxylic acids, alcohols, and amines?

Accepted Answer

Carboxylic acids \u003e alcohols \u003e amines

Question 6

Given the electronegativities: C (2.55), H (2.20), N (3.04), O (3.44), which bond is the most polar?

Accepted Answer

$$ \mathrm{O-H} $$

Question 7

Which of the following compounds is most likely to undergo nucleophilic addition-elimination reactions?

Accepted Answer

Carboxylic acid ($$ \mathrm{RCOOH} )$$

Question 8

Which of the following is the correct order of increasing SN2 reactivity for the following alkyl halides: methyl bromide, isopropyl bromide, tert-butyl bromide?

Accepted Answer

tert-butyl bromide \u003c isopropyl bromide \u003c methyl bromide

Question 9

A molecule with the structure shown in the stained glass (second image) is best classified as which of the following?

Accepted Answer

Peptide

Question 10

Which of the following best explains why carboxylic acids are more acidic than alcohols?

Accepted Answer

The carboxylate ion is resonance stabilized.

Question 11

Which of the following is the correct product for the reaction of $$ \mathrm{CH_3CH_2Br} $$ with KOH in ethanol?

Accepted Answer

$$ \mathrm{CH_3CH_2OH} $$

Question 12

Which of the following best describes the mechanism for the reaction of a carboxylic acid with an alcohol under acidic conditions?

Accepted Answer

Nucleophilic addition-elimination

Question 13

Which of the following statements is true regarding the pKa values of amines compared to alcohols?

Accepted Answer

Amines have higher pKa values than alcohols.

Question 14

Which of the following is the best explanation for the trend in SN2 reactivity among primary, secondary, and tertiary alkyl halides?

Accepted Answer

Steric hindrance increases from primary to tertiary, decreasing reactivity.

Question 15

Which of the following is the correct order of increasing acidity: $$ \mathrm{H_2O} $$, $$ \mathrm{CH_3OH} $$, $$ \mathrm{NH_3} $$?

Accepted Answer

$$ \mathrm{NH_3} \u003c \mathrm{CH_3OH} \u003c \mathrm{H_2O} $$

Question 16

Which of the following best describes the class of pharmaceuticals to which the molecule in the stained glass belongs?

Accepted Answer

Peptide hormones

Organic Chemistry Study Guidance: Acidity, SN2, Addition-Elimination, pKa, Mechanisms, and Pharmaceutical Structure

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