Question 1

Which of the following molecules has a net molecular dipole moment pointing from the oxygen atom toward the hydrogen atoms?

Accepted Answer

Water ($$\ce{H2O})$$

Question 2

Which type of intermolecular force is primarily responsible for the high boiling point of ethanol ($$\ce{CH3CH2OH}) $$compared to ethane ($$\ce{CH3CH3}$$)?

Accepted Answer

Hydrogen bonding

Question 3

Which of the following molecules can participate in hydrogen bonding with water?

Accepted Answer

Acetone ($$\ce{CH3COCH3})$$

Question 4

Which of the following statements best explains why sodium chloride ($$\ce{NaCl}) is $$highly soluble in water but not in hexane?

Accepted Answer

Water can stabilize ions through ion-dipole interactions, while hexane cannot.

Question 5

Which electrons in the acetate ion ($$\ce{CH3COO^-}) $$are delocalized via resonance?

Accepted Answer

The lone pair electrons on the two oxygen atoms

Question 6

Which of the following is the major resonance contributor for the formate ion ($$\ce{HCO2^-}$$)?

Accepted Answer

The structure in which both oxygen atoms bear a formal charge of -0.5 and share the negative charge equally.

Question 7

Which curved arrow best represents the first step in the resonance delocalization of the allyl cation ($$\ce{CH2=CH-CH2^+}$$)?

Accepted Answer

From the double bond to the adjacent carbon atom bearing the positive charge

Question 8

Which of the following molecules can act as both a Brønsted-Lowry acid and a Brønsted-Lowry base?

Accepted Answer

Water ($$\ce{H2O})$$

Question 9

Given the following pKa values: acetic acid ($$\ce{CH3COOH}) = 4.8$$, phenol ($$\ce{C6H5OH}) = 10$$, and ethanol ($$\ce{CH3CH2OH}) = 16. $$Which is the strongest acid?

Accepted Answer

Acetic acid

Question 10

Consider the acid-base reaction: $$\ce{CH3COOH + NH3  CH3COO^- + NH4^+}. $$Given that the pKa of acetic acid is 4.8 and the pKa of ammonium ion is 9.2, which direction does the equilibrium favor?

Accepted Answer

Toward the products ($$\ce{CH3COO^-}$$ and $$\ce{NH4^+})$$

Question 11

Which structural feature most increases the acidity of a hydrogen atom in a molecule, according to the ARIO principle?

Accepted Answer

Resonance stabilization of the conjugate base

Question 12

Which proton is most acidic in acetylacetone ($$\ce{CH3COCH2COCH3}$$)?

Accepted Answer

The hydrogen atom on the central methylene group ($$\ce{CH2})$$

Question 13

Which solvent would be most appropriate for a reaction involving a very strong base such as sodium amide ($$\ce{NaNH2}$$)?

Accepted Answer

Liquid ammonia ($$\ce{NH3})$$

Question 14

Which of the following is a consequence of the leveling effect in acid-base chemistry?

Accepted Answer

The strongest acid that can exist in water is the hydronium ion ($$\ce{H3O^+})$$

Question 15

What is the IUPAC name for the following compound: $$\ce{(CH3)2CHCH2CH3}$$?

Accepted Answer

2-Methylbutane

Question 16

Which of the following pairs are constitutional isomers?

Accepted Answer

n-Butane and isobutane

Question 17

Which alkane would have the highest heat of combustion per mole?

Accepted Answer

Cyclopropane

Question 18

Which conformation of butane ($$\ce{CH3CH2CH2CH3}) is $$the most stable?

Accepted Answer

Anti conformation (methyl groups 180° apart)

Question 19

Which of the following functional groups is present in both acetone and acetic acid?

Accepted Answer

Carbonyl group ($$\ce{C=O})$$

Fundamentals of Organic Molecules: Intermolecular Forces, Resonance, Acidity, and Alkanes

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