Question 1

Which of the following statements best describes the difference between constitutional isomers and stereoisomers?

Accepted Answer

Constitutional isomers differ in connectivity of atoms; stereoisomers have the same connectivity but differ in spatial arrangement.

Question 2

Which of the following alkyl halides would most likely undergo an $$S_N1$$ reaction rather than an $$S_N2$$ reaction?

Accepted Answer

tert-butyl chloride

Question 3

A student is asked to assign the absolute configuration (R or S) to the following chiral center: $$CH_3CH(Br)CH_2OH. $$Which of the following is the correct configuration?

Accepted Answer

S

Question 4

Which of the following best explains why child compounds often display a net dipole moment?

Accepted Answer

Child compounds contain polar bonds arranged asymmetrically.

Question 5

Which of the following is a correct statement about the rate-determining step in a multistep reaction?

Accepted Answer

It is the slowest step and determines the overall reaction rate.

Question 6

Which of the following is the best nucleophile in a polar aprotic solvent?

Accepted Answer

$$F^-$$

Question 7

Which of the following reactions is most likely to result in the formation of a carbocation intermediate?

Accepted Answer

$$S_N1$$ substitution

Question 8

A chemist wants to favor the kinetic product in an elimination reaction. Which of the following conditions should be used?

Accepted Answer

Low temperature and a bulky base

Question 9

Which of the following best describes the transition state of an $$S_N2$$ reaction?

Accepted Answer

A pentavalent carbon with partial bonds to both nucleophile and leaving group

Question 10

Which of the following is the correct order of leaving group ability for the halides?

Accepted Answer

$$I^- \u003e Br^- \u003e Cl^- \u003e F^-$$

Question 11

Which of the following statements about E2 elimination reactions is correct?

Accepted Answer

E2 reactions are concerted and require anti-coplanar geometry between the leaving group and the hydrogen being abstracted.

Question 12

Which of the following best explains why tertiary alkyl halides do not undergo $$S_N2$$ reactions efficiently?

Accepted Answer

Steric hindrance prevents the nucleophile from attacking the carbon center.

Question 13

Which of the following is a correct statement about the use of $$\Delta G^\circ in $$predicting reaction spontaneity?

Accepted Answer

$$\Delta G^\circ$$ \u003c 0$ indicates a spontaneous reaction.

Question 14

Which of the following is the correct IUPAC name for the compound $$CH_3CH_2CH_2Br$$?

Accepted Answer

1-bromopropane

Question 15

A reaction mechanism involves the following steps: (1) formation of a carbocation, (2) nucleophilic attack, (3) deprotonation. Which type of reaction is this most likely to be?

Accepted Answer

$$S_N1$$ substitution

Question 16

Which of the following statements about the $$S_N2$$ reaction mechanism is correct?

Accepted Answer

The reaction rate depends on the concentrations of both the substrate and the nucleophile.

Question 17

Which of the following is the best description of a concerted reaction mechanism?

Accepted Answer

A mechanism in which all bond breaking and forming occurs in a single step.

Question 18

Which of the following is a common misconception about nucleophilicity?

Accepted Answer

Nucleophilicity is the same as basicity in all cases.

Question 19

Which of the following statements about the use of reaction energy diagrams is correct?

Accepted Answer

The highest point on the diagram corresponds to the transition state.

Organic Chemistry: Reaction Mechanisms, Stereochemistry, and Alkyl Halides

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