Question 1

What is the correct IUPAC name for the following alkene alcohol?

(Refer to the structure: a five-carbon chain with a double bond between C3 and C4, a hydroxy group at C2, an ethyl group at C3, and a methyl group at C4.)

Accepted Answer

3-ethyl-4-methylpent-3-en-2-ol

Question 2

Which of the following pK$$_a$$ values corresponds to the strongest acid?

Accepted Answer

$$-8$$

Question 3

Which of the following pK$$_a$$ values corresponds to the weakest acid?

Accepted Answer

$$50$$

Question 4

In the series of molecules shown (benzyl anion, cyclohexyl anion, pyridine anion, nitrobenzoate anion, cyclohexanone anion), which is the most basic?

Accepted Answer

Cyclohexyl anion

Question 5

In the same series, which is the least basic?

Accepted Answer

Nitrobenzoate anion

Question 6

Given the following compounds and their pK$$_a$$ values, which is the strongest base?

- Alkane: $$pK_a = 50
- $$Ammonium ion: $$pK_a = 10
- $$Phenol: $$pK_a = 16
- $$Benzene: $$pK_a = 43$$

Accepted Answer

Alkane

Question 7

Rank the following molecules from most acidic to least acidic:

- Cyclohexanol
- p-Trifluoromethylphenol
- Phenol

Accepted Answer

p-Trifluoromethylphenol \u003e Phenol \u003e Cyclohexanol

Question 8

Which of the following bicyclic ketones is a stronger acid?

(Refer to the image: left is bicyclo[2.2.1]heptan-2-one, right is bicyclo[2.2.1]heptan-7-one)

Accepted Answer

The left molecule (bicyclo[2.2.1]heptan-2-one)

Question 9

For the following compounds, which proton is the most acidic?

(Refer to the image: indole, barbituric acid, citric acid)

Accepted Answer

The N-H proton in indole, the alpha proton between two carbonyls in barbituric acid, and the carboxylic acid proton in citric acid

Question 10

Given the reaction:

$$\mathrm{C_6H_5O^-} + \mathrm{CH_3CH_2OH} \rightleftharpoons \mathrm{C_6H_5OH} + \mathrm{CH_3CH_2O^-}$$

with $$pK_a$$ values $$15.9 ($$phenol) and $$10 ($$ethanol), does the equilibrium favor products or reactants?

Accepted Answer

Reactants

Question 11

Determine if the following molecule is chiral or achiral:

(Refer to the image: bicyclo[2.2.1]heptane with two Br and two methyl groups on bridgehead carbons)

Accepted Answer

Achiral

Question 12

Are the following two molecules enantiomers, diastereomers, or the same?

(Refer to the image: two cyclopentane rings with two OH groups in different positions)

Accepted Answer

Diastereomers

Question 13

Which of the following molecules will undergo $$S_N1$$, $$S_N2$$, $$E1$$, or $$E2$$ reactions?

(Refer to the image: two quaternary ammonium salts, one aliphatic, one benzylic)

Accepted Answer

The benzylic ammonium salt

Question 14

Predict the product for the acid-catalyzed hydration of 2-methyl-2-butene with dilute $$\mathrm{H_2SO_4}.$$

Accepted Answer

2-methyl-2-butanol (major) and 2-methyl-1-butanol (minor)

Question 15

What is the major product of the reaction of 1-methylcyclopentene with HCl?

Accepted Answer

1-chloro-2-methylcyclopentane

Organic Chemistry Study Guide: Nomenclature, Acidity, Basicity, Chirality, and Reaction Mechanisms

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