Question 1

Which of the following statements best describes the concept of aromaticity in organic chemistry?

Accepted Answer

Aromatic compounds are cyclic, planar, fully conjugated molecules that follow Hückel's rule ($$4n+2$$ $$	ext{π}$$ electrons).

Question 2

Which reagent would best convert a primary alcohol to an aldehyde without further oxidation to a carboxylic acid?

Accepted Answer

Pyridinium chlorochromate (PCC)

Question 3

A student reacts benzene with bromine ($$\mathrm{Br_2$}) in $$the presence of iron(III) bromide ($$\mathrm{$$FeBr_3$$}). $$What type of reaction is this?

Accepted Answer

Electrophilic aromatic substitution

Question 4

Which of the following molecules is NOT aromatic?

Accepted Answer

Cyclobutadiene

Question 5

What is the major product when 2-methyl-2-butanol is treated with concentrated sulfuric acid ($$\mathrm{H_2SO_4}) $$and heated?

Accepted Answer

2-methyl-2-butene

Question 6

Which of the following statements about SN1 and SN2 reactions is correct?

Accepted Answer

SN2 reactions are stereospecific and result in inversion of configuration.

Question 7

A chemist wants to synthesize tert-butyl ethyl ether using an alcohol and an alkyl halide. Which combination and reaction mechanism would be most effective?

Accepted Answer

Reacting ethyl alcohol with tert-butyl bromide via SN1 mechanism

Question 8

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

$$\mathrm{CH_3CH_2COCH_3}$$

Accepted Answer

2-butanone

Question 9

Which of the following statements best explains why benzene is less reactive than alkenes toward bromine addition?

Accepted Answer

Benzene's delocalized $$\pi$$ electrons provide extra stability, making addition reactions energetically unfavorable.

Question 10

A student is asked to predict the product of the following reaction:

$$\mathrm{CH_3CH_2OH}$$ + $$\mathrm{H_2SO_4} ($$heat)

What is the major organic product?

Accepted Answer

Ethene ($$\mathrm{CH_2$=CH_2$})$$

Question 11

Which of the following compounds will react fastest in an SN1 reaction?

Accepted Answer

tert-butyl chloride

Question 12

Which of the following is the correct order of acidity (most acidic to least acidic) for the following compounds?

1. Ethanol ($$\mathrm{CH_3CH_2OH})
2. $$Acetic acid ($$\mathrm{CH_3COOH})
3. $$Phenol ($$\mathrm{C_6H_5OH})$$

Accepted Answer

Acetic acid \u003e Phenol \u003e Ethanol

Question 13

A patient is exposed to methanol ($$\mathrm{CH_3OH}) $$poisoning. Which metabolic product is responsible for the toxic effects?

Accepted Answer

Formic acid ($$\mathrm{HCOOH})$$

Question 14

Which of the following reactions is used in the laboratory to test for the presence of aldehydes?

Accepted Answer

Tollens' test (silver mirror test)

Question 15

Which of the following statements about stereochemistry is correct?

Accepted Answer

Enantiomers have identical physical properties except for their interaction with plane-polarized light.

Question 16

Which of the following is the major product when 1-bromopropane reacts with sodium ethoxide ($$\mathrm{NaOEt}) in $$ethanol?

Accepted Answer

Propene

Question 17

A student is asked to draw the mechanism for the acid-catalyzed hydration of 2-methylpropene. What is the first step in this mechanism?

Accepted Answer

Protonation of the alkene to form a carbocation

Question 18

Which of the following statements best explains why tertiary alcohols are more resistant to oxidation than primary alcohols?

Accepted Answer

Tertiary alcohols lack a hydrogen atom on the carbon bearing the hydroxyl group.

Question 19

Which of the following is the correct product of the reaction between benzaldehyde and acetone in the presence of a base?

Accepted Answer

An aldol condensation product: $$\mathrm{C_6H_5CH=$$CHCOCH_3$$}$$

Organic Chemistry I Syllabus and Course Structure

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