Question 1

Which of the following statements best explains why the hydrogen atom in molecule A ($$\mathrm{HC\equiv C-CO_2$}) is $$more acidic than in molecule B ($$\mathrm{HC\equiv C-CH_3$}$$)?

Accepted Answer

The carboxyl group in molecule A stabilizes the conjugate base via resonance, increasing acidity.

Question 2

How many atoms in the following molecule are $$sp^2$$ hybridized? (Refer to the structure in question 2 of the exam.)

Accepted Answer

$$7$$

Question 3

Which of the following best describes the group circled in the compound in question 3 of the exam?

Accepted Answer

sec-butyl

Question 4

For the Newman projection of Compound A, which conformation is most stable?

Accepted Answer

Staggered conformation with bulky groups anti

Question 5

Which of the following species can be classified as a Lewis acid?

Accepted Answer

$$\mathrm{$$AlCl_3$$}$$

Question 6

Given the following reaction mechanism, what is the major product? (Refer to question 6 of the exam.)

Accepted Answer

tert-butyl cyclohexane

Question 7

During a chair flip of substituted cyclohexane X, which position is preferred for a bulky substituent to minimize steric strain?

Accepted Answer

Equatorial

Question 8

In the energy diagram for a two-step reaction, which step corresponds to the highest activation energy?

Accepted Answer

Step 1

Question 9

Which of the following is the correct Lewis structure for $$\mathrm{CH_3CH_2CH_2CH_2CH_2Cl}$$?

Accepted Answer

$$\mathrm{Cl-CH_2$-CH_2$-CH_2$-CH_2$-CH_3$}$$

Question 10

Which of the following is the correct skeletal structure for $$\mathrm{CH_3CH_2CH_2CH_2CH_2Cl}$$?

Accepted Answer

A five-carbon chain with a chlorine on the terminal carbon

Question 11

Which of the following is the correct acid-base reaction for the equilibrium between cyclohexanol and sodium hydride?

Accepted Answer

$$\mathrm{C_6H_{11}OH + NaH \rightarrow C_6H_{11}O^- + Na^+ + H_2$}$$

Question 12

Which of the following is the correct conjugate base for cyclohexanol?

Accepted Answer

$$\mathrm{C_6H_{11}O^-}$$

Question 13

Which of the following best describes the role of $$\mathrm{$$AlCl_3$$} in a $$Friedel-Crafts alkylation reaction?

Accepted Answer

Lewis acid catalyst that activates the alkyl halide

Question 14

Which of the following is a correct statement about resonance stabilization in carboxylate ions?

Accepted Answer

Resonance delocalizes negative charge over two oxygen atoms, stabilizing the ion.

Question 15

Which of the following is true about the hybridization of the carbon atom in a carbonyl group ($$\mathrm{C=O}$$)?

Accepted Answer

The carbon is $$sp^2$$ hybridized.

Question 16

Which of the following is the correct IUPAC name for the molecule shown in question 3 of the exam?

Accepted Answer

3-chloro-4-isopropylheptane

Question 17

Which of the following best describes the transition state in a two-step reaction mechanism?

Accepted Answer

It is the highest energy point between reactants and products.

Question 18

Which of the following is a correct statement about the inductive effect of a methyl group attached to an alkyne?

Accepted Answer

A methyl group is an electron-donating group and decreases the acidity of the adjacent hydrogen.

Question 19

Which of the following is true about the energy difference between axial and equatorial positions in cyclohexane?

Accepted Answer

Bulky groups prefer the equatorial position due to lower steric strain.

Organic Chemistry Exam I Study Guide: Acids/Bases, Hybridization, Nomenclature, Conformations, Mechanisms, and Lewis Structures

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