Q: Which of the following reactions is an example of a condensation reaction?

Aldol reaction forming a $$eta-$$hydroxy ketone

Question 1

Which of the following statements best explains why benzene is more stable than expected for a molecule with three double bonds?

Accepted Answer

Benzene's six pi electrons are delocalized over the ring, resulting in resonance stabilization.

Question 2

A compound with the molecular formula $$C_4H_{10}O$$ shows a strong, broad absorption around $$3300\ 	ext{cm}^{-1} in $$its IR spectrum. Which functional group is most likely present?

Accepted Answer

Alcohol

Question 3

Which of the following is the correct IUPAC name for the compound with the structure $$CH_3COOCH_2CH_3$$?

Accepted Answer

Ethyl acetate

Question 4

In the $$^1H$$ NMR spectrum of ethyl benzene, which of the following signals would you expect to appear as a quartet?

Accepted Answer

The methylene protons ($$CH_2) $$adjacent to the aromatic ring

Question 5

Which of the following reagents would best convert a primary alcohol to a carboxylic acid?

Accepted Answer

$$KMnO_4 ($$Potassium permanganate) under acidic conditions

Question 6

A student is given an unknown compound and its mass spectrum shows a molecular ion peak at $$m/z = 58. $$The IR spectrum shows a strong absorption at $$1715\ 	ext{cm}^{-1}. $$Which compound is most likely?

Accepted Answer

Acetone

Question 7

Which of the following best describes the mechanism of electrophilic aromatic substitution (EAS) in benzene?

Accepted Answer

An electrophile adds to the ring, forming a carbocation intermediate, followed by deprotonation to restore aromaticity.

Question 8

Which of the following compounds will react most rapidly with $$NaOCH_3 in $$methanol via an $$S_N2$$ mechanism?

Accepted Answer

Benzyl chloride

Question 9

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

Accepted Answer

NaOH (aqueous)

Question 10

Which of the following statements about the reactivity of carboxylic acid derivatives is correct?

Accepted Answer

Esters are less reactive than anhydrides.

Question 11

Which of the following best describes the product of the reaction between benzene and $$CH_3Cl in $$the presence of $$AlCl_3$$?

Accepted Answer

Toluene

Question 12

A compound with the formula $$C_3H_7NO_2 is $$found to be an amine. Which of the following is the most likely structure?

Accepted Answer

Glycine

Question 13

Which of the following reactions is an example of a condensation reaction?

Accepted Answer

Aldol reaction forming a $$eta-$$hydroxy ketone

Question 14

Which of the following statements about the $$\alpha-$$hydrogen of carbonyl compounds is correct?

Accepted Answer

The $$\alpha-$$hydrogen is more acidic due to resonance stabilization of the enolate ion.

Question 15

Which of the following best describes the splitting pattern for the methyl group in ethyl acetate ($$CH_3COOCH_2CH_3) in $$its $$^1H$$ NMR spectrum?

Accepted Answer

Triplet

Question 16

Which of the following is a correct statement about the UV-Vis absorption of conjugated systems?

Accepted Answer

Increasing conjugation shifts the absorption maximum ($$\lambda_{max}) to $$longer wavelengths.

Question 17

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

Accepted Answer

Ethanol \u003c phenol \u003c acetic acid

Question 18

A student is given a mixture of an ether and an alcohol. Which of the following tests would best distinguish between the two?

Accepted Answer

Addition of sodium metal to observe hydrogen gas evolution

Question 19

Which of the following best describes the product of the reaction between cyclohexanone and hydrazine ($$NH_2NH_2) $$under basic conditions (Wolff-Kishner reduction)?

Accepted Answer

Cyclohexane

Question 20

Which of the following statements about the mechanism of nucleophilic addition to aldehydes and ketones is correct?

Accepted Answer

The nucleophile attacks the carbonyl carbon, forming a tetrahedral intermediate.

Organic Chemistry II (CHEM 222) Syllabus and Study Guide – Community College of Philadelphia

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