Question 1

Which of the following statements best explains why water ($$\mathrm{H_2O}) $$has a higher boiling point than methane ($$\mathrm{CH_4$}$$)?

Accepted Answer

Water forms hydrogen bonds, which are stronger than the London dispersion forces present in methane.

Question 2

Which of the following is the correct IUPAC name for the compound with the structure $$\mathrm{CH_3CH_2CH_2Br}$$?

Accepted Answer

1-Bromopropane

Question 3

Which of the following statements about SN2 reactions is correct?

Accepted Answer

The rate of an SN2 reaction depends on the concentration of both the nucleophile and the substrate.

Question 4

Which of the following compounds will have the highest boiling point?

Accepted Answer

$$\mathrm{CH_3CH_2OH} ($$ethanol)

Question 5

Which of the following is the best description of the hybridization of the central carbon atom in ethene ($$\mathrm{C_2H_4}$$)?

Accepted Answer

$$sp^2$$

Question 6

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

Accepted Answer

E2 reactions require a strong base and proceed in a single concerted step.

Question 7

Which of the following is the correct order of increasing acidity for the following compounds: $$\mathrm{CH_4$}$$, $$\mathrm{NH_3$}$$, $$\mathrm{H_2O}$$, $$\mathrm{HF}$$?

Accepted Answer

$$\mathrm{CH_4$} \u003c \mathrm{NH_3$} \u003c \mathrm{H_2O} \u003c \mathrm{HF}$$

Question 8

Which of the following is a correct statement about the Markovnikov rule in the addition of $$\mathrm{HBr} to $$propene ($$\mathrm{CH_3CH=CH_2$}$$)?

Accepted Answer

The bromine atom attaches to the more substituted carbon atom of the double bond.

Question 9

Which of the following reagents would best convert 1-butyne ($$\mathrm{CH_3CH_2C \equiv CH}) to a $$cis-2-butene ($$\mathrm{CH_3CH=$$CHCH_3$$}$$)?

Accepted Answer

Lindlar's catalyst with $$\mathrm{H_2$}$$

Question 10

Which of the following statements about meso compounds is correct?

Accepted Answer

Meso compounds are achiral despite having stereocenters due to an internal plane of symmetry.

Question 11

Which of the following best describes the product of the reaction of 2-bromopropane with sodium ethoxide ($$\mathrm{NaOEt}) in $$ethanol?

Accepted Answer

Propene ($$\mathrm{CH_2$=$$CHCH_3$$}) $$via E2 elimination

Question 12

Which of the following is the correct IUPAC name for the compound below?

$$\mathrm{CH_3CH_2CH_2OH}$$

Accepted Answer

1-Propanol

Question 13

Which of the following statements about the reaction of alkenes with $$\mathrm{Br_2$} in$$ $$\mathrm{$$CCl_4$$} is $$correct?

Accepted Answer

The reaction proceeds via an anti addition to give a vicinal dibromide.

Question 14

Which of the following is the best explanation for why tertiary alkyl halides react faster than primary alkyl halides in SN1 reactions?

Accepted Answer

Tertiary carbocations are more stable due to hyperconjugation and inductive effects.

Question 15

Which of the following is the correct product when 2-methyl-2-butene reacts with $$\mathrm{H_2SO_4}$$ and water?

Accepted Answer

2-Methyl-2-butanol

Question 16

Which of the following statements about the physical properties of alkanes is correct?

Accepted Answer

Branched alkanes have lower boiling points than their straight-chain isomers.

Question 17

Which of the following best describes the product of the ozonolysis of cyclohexene followed by reduction with zinc?

Accepted Answer

Adipaldehyde ($$\mathrm{OHC(CH_2$)_4CHO})$$

Question 18

Which of the following is the correct order of increasing nucleophilicity in polar aprotic solvents: $$\mathrm{F^-}$$, $$\mathrm{Cl^-}$$, $$\mathrm{Br^-}$$, $$\mathrm{I^-}$$?

Accepted Answer

$$\mathrm{F^-} \u003c \mathrm{Cl^-} \u003c \mathrm{Br^-} \u003c \mathrm{I^-}$$

Question 19

Which of the following statements about the reaction of alkynes with $$\mathrm{$$NaNH_2$$} is $$correct?

Accepted Answer

Terminal alkynes are deprotonated to form acetylide anions.

Question 20

Which of the following is the correct product when 1-butyne reacts with excess $$\mathrm{Br_2$}$$?

Accepted Answer

1,1,2,2-Tetrabromobutane

Organic Chemistry I: Final Exam Review Topics and Study Guide

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