Question 1

Which of the following functional groups is present in Penicillin G, as shown in the exam image?

Accepted Answer

Lactam

Question 2

Given the following reaction: $$\mathrm{CH_3COCH_2COCH_3} + \mathrm{C_2H_5OK} \rightleftharpoons$$ products, which factor most strongly favors the formation of products?

Accepted Answer

The formation of a weaker base

Question 3

Which of the following molecules is chiral?

Accepted Answer

2-butanol

Question 4

How many $$sp^2$$ hybridized carbon atoms are present in the structure of Adcirca (Tadalafil) shown in the exam?

Accepted Answer

10

Question 5

Which of the following best describes the relationship between the two molecules shown in part (b)(i) of the exam (the Fischer projections of sugars)?

Accepted Answer

Diastereomers

Question 6

What is the major resonance contributor for the molecule shown in part (a) of the resonance section (acetophenone)?

Accepted Answer

The structure with the negative charge on the oxygen atom

Question 7

Which of the following is the correct IUPAC name for the molecule shown in part (c) of the IUPAC naming section (the bicyclic amine)?

Accepted Answer

1-azabicyclo[2.2.2]octane

Question 8

In the chair conformation of cyclohexane shown in the exam, which substituent position is generally more stable for a bulky group such as $$\mathrm{tBu}$$?

Accepted Answer

Equatorial

Question 9

Which of the following statements about the acid-base reaction shown in the exam (ketone + alkoxide) is correct?

Accepted Answer

The equilibrium favors the side with the weaker base

Question 10

How many stereoisomers are possible for the molecule Adcirca (Tadalafil) shown in the exam?

Accepted Answer

8

Question 11

Which of the following best explains why the chair conformation with the $$\mathrm{NH_2$}$$ group in the equatorial position is more stable than the axial position?

Accepted Answer

Minimizes 1,3-diaxial interactions

Question 12

Which of the following molecules contains an aromatic ring?

Accepted Answer

Benzene

Question 13

In the resonance structures of acetophenone, which atom is most likely to bear a negative charge in one of the resonance forms?

Accepted Answer

Oxygen

Question 14

Which of the following is a constitutional isomer of 2-methylpentane?

Accepted Answer

2,2-dimethylbutane

Question 15

How many unhybridized $$p-$$orbitals are present in the structure of Adcirca (Tadalafil)?

Accepted Answer

12

Question 16

Which of the following best describes the product of the acid-base reaction between a ketone and an alkoxide?

Accepted Answer

An enolate ion and an alcohol

Question 17

Which of the following molecules is achiral?

Accepted Answer

2,3-dimethylbutane

Question 18

Which of the following is the correct Newman projection for the most stable conformation of ethane?

Accepted Answer

Staggered conformation

Question 19

Which of the following is the correct electron movement for the resonance structure of acetophenone?

Accepted Answer

From the lone pair on oxygen to form a double bond with carbon

Question 20

Which of the following is the correct IUPAC name for the molecule shown in part (a) of the IUPAC naming section (the branched alkane)?

Accepted Answer

3-ethyl-2,4-dimethylpentane

Organic Chemistry Exam Study Guide: Functional Groups, Isomerism, Resonance, Acid-Base Chemistry, Stereochemistry, and Molecular Structure

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