Question 1

Which of the following statements best describes the difference between alkanes and alkenes?

Accepted Answer

Alkanes contain only single carbon-carbon bonds ($$\ce{C-C}$$), while alkenes contain at least one carbon-carbon double bond ($$\ce{C=C}).$$

Question 2

Which of the following is the correct IUPAC name for the compound with the structure $$\ce{CH3CH2CH=CH2}$$?

Accepted Answer

1-butene

Question 3

A student is asked to identify the major product of the reaction between 2-methylpropene and HBr. Which rule should the student apply to predict the major product?

Accepted Answer

Markovnikov's rule

Question 4

Which of the following compounds is most likely to undergo an $$\ce{S_N1}$$ reaction mechanism when reacted with a strong nucleophile?

Accepted Answer

tert-butyl chloride ($$\ce{(CH3)3CCl})$$

Question 5

Which of the following statements about aromaticity is correct?

Accepted Answer

Aromatic compounds must be cyclic, planar, fully conjugated, and follow Hückel's rule ($$4n+2$$ $$\pi$$ electrons).

Question 6

Which of the following is the correct product of the reaction between benzene and bromine ($$\ce{Br2}) in $$the presence of iron(III) bromide ($$\ce{FeBr3}$$)?

Accepted Answer

Bromobenzene

Question 7

A compound is found to have the molecular formula $$\ce{C4H8O}. It $$reacts with sodium metal to produce hydrogen gas and forms a silver mirror with Tollens' reagent. Which functional group is most likely present?

Accepted Answer

Aldehyde

Question 8

Which of the following best explains why tertiary alcohols are more reactive than primary alcohols in acid-catalyzed dehydration reactions?

Accepted Answer

Tertiary alcohols form more stable carbocations during the reaction.

Question 9

Which of the following statements about the stereochemistry of alkenes is correct?

Accepted Answer

Cis and trans isomers of alkenes differ in the spatial arrangement of substituents around the double bond.

Question 10

A student is given a mixture of 1-bromobutane and 2-bromobutane. Which test could be used to distinguish between these two compounds?

Accepted Answer

Reaction with aqueous silver nitrate ($$\ce{AgNO3})$$

Question 11

Which of the following is the correct order of acidity for the following compounds: ethanol, acetic acid, and phenol?

Accepted Answer

Acetic acid \u003e phenol \u003e ethanol

Question 12

Which of the following reactions is an example of an electrophilic aromatic substitution?

Accepted Answer

Bromination of benzene with $$\ce{Br2}$$ and $$\ce{FeBr3}$$

Question 13

Which of the following best describes the hybridization of the carbon atoms in ethyne ($$\ce{C2H2}$$)?

Accepted Answer

$$\mathrm{sp}$$

Question 14

A student is asked to synthesize 2-butanol from 1-butene. Which of the following reagents would be most appropriate for this transformation?

Accepted Answer

Oxymercuration-demercuration ($$\ce{Hg(OAc)2}$$, $$\ce{H2O}$$, $$\ce{NaBH4})$$

Question 15

Which of the following statements about the reaction mechanism of $$\ce{S_N2}$$ reactions is correct?

Accepted Answer

The reaction involves a backside attack and inversion of configuration at the carbon center.

Question 16

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

Accepted Answer

1,1-dibromobutane

Question 17

Which of the following best explains why ethers are generally unreactive toward nucleophilic substitution under neutral conditions?

Accepted Answer

The oxygen atom in ethers is not sufficiently electrophilic.

Question 18

A patient is exposed to carbon monoxide ($$\ce{CO}) $$poisoning. Which property of $$\ce{CO}$$ makes it so dangerous in the human body?

Accepted Answer

$$\ce{CO}$$ binds more strongly to hemoglobin than oxygen, reducing oxygen delivery to tissues.

Question 19

Which of the following is the correct product of the reaction of 1,2-epoxypropane (propylene oxide) with aqueous acid?

Accepted Answer

1,2-propanediol

Question 20

Which of the following best describes the effect of electron-withdrawing groups on the acidity of phenol?

Accepted Answer

Electron-withdrawing groups increase the acidity of phenol by stabilizing the phenoxide ion.

Organic Chemistry I (CHEM 201) Syllabus and Study Guide

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