Chapter 19

I > II > IV > III

Arrange the following compounds in order of decreasing water solubility, putting the most soluble compound first.

IV < III < II < I

Arrange the following compounds in order of increasing acidity, putting the least acidic first.

I < IV < II < III

Arrange the following compounds in order of increasing boiling point, putting the compound with the lowest boiling point first.

IV < II < III < I

Arrange the following compounds in order of increasing water solubility, putting the least soluble compound first.

D

As applied to the chemistry of amino acids, what is the definition for the isoelectric point? A. The pH at which the amino acid exists primarily in its acidic form. B. The pH at which the amino acid exists primarily in its basic form. C. The pH at which the amino acid exists as a mixture of isomers. D. The pH at which the amino acid exists primarily in its neutral form.

A

In the presence of strong acids, which of the oxygen atoms on the carboxyl group is preferentially protonated and why? A. Protonation occurs at the carbonyl oxygen because the resulting conjugate acid is stabilized by resonance. B. Protonation occurs at the carbonyl oxygen because the resulting conjugate base is stabilized by the inductive effect. C. Protonation occurs at the hydroxyl oxygen because the resulting conjugate acid is stabilized by resonance. D. Protonation occurs at the hydroxyl oxygen because the resulting conjugate base is stabilized by the inductive effect.

I < IV < II < III

Rank the following compounds in order of increasing acidity, putting the least acidic first.

II < I < III < IV

Rank the following compounds in order of increasing acidity, putting the least acidic first.

II > I > III > IV

Rank the following compounds in order of decreasing acidity, putting the most acidic first.

IV > III > II > I

Rank the following compounds in order of decreasing acidity, putting the most acidic first.

IV < I < II < III

Rank the following compounds in order of increasing acidity, putting the least acidic compound first.

IV < I < II < III

Rank the following compounds in order of increasing acidity, putting the least acidic first.

B

Rank the labeled protons (Ha-Hd) in order of increasing acidity, starting with the least acidic. A. Ha < Hb < Hc < Hd B. Hb < Hc < Ha < Hd C. Hd < Ha < Hc < Hb D. Hb < Hc < Hd < Ha

B

What is the correct IUPAC name of the following compound? A. (E)-2-Hexenoic acid B. (Z)-2-Hexenoic acid C. (E)-4-Hexenoic acid D. (Z)-4-Hexenoic acid

D

What is the correct IUPAC name of the following compound? A. 2-Methoxypentanoic acid B. 2-Methoxybutanoic acid C. 4-Methoxybutanoic acid D. 4-Methoxypentanoic acid

A

What is the correct IUPAC name of the following compound? A. 2-sec-Butyl-4,4-dimethylnonanoic acid B. 4,4-Dimethyl-2-isobutylnonanoic acid C. 4,4-Dimethyl-2-sec-butylnonanoic acid D. 2-Isobutyl-4,4-dimethylnonanoic acid

B

What is the correct IUPAC name of the following compound? A. 3,4-Dimethylcyclohexanoic acid B. 3,4-Dimethylcyclohexanecarboxylic acid C. 4,5-Dimethylcyclohexanecarboxylic acid D. 1,2-Dimethylcyclohexanecarboxylic acid

B

What is the correct IUPAC name of the following compound? A. 3,5,5-Trimethylcyclohexanecarboxylic acid B. 3,3,5-Trimethylcyclohexanecarboxylic acid C. 3,3,5-Trimethylcyclohexanoic acid D. 3,5,5-Trimethylcyclohexanoic acid

C

What is the correct IUPAC name of the following compound? A. 4-Isopropyl-3-methylbutanoic acid B. 2,4-Dimethylhexanoic acid C. 3,5-Dimethylhexanoic acid D. 3,5-Dimethy-1-hexanoic acid

B

What is the hybridization of the carbon atom in a carboxy group? A. sp B. sp2 C. sp3 D. p

C

What is the other product formed in the oxidation of the following terminal alkyne? A. HCOOH B. HCOH C. CO2 D. CO

B

What is the overall charge of the amino acid, alanine, at pH = 10? A. + 1 B. - 1 C. No overall charge D. - 2

A

What is the overall charge of the amino acid, alanine, at pH = 2? A. + 1 B. - 1 C. No overall charge D. + 2

C

What is the overall charge of the amino acid, alanine, at pH = 7? A. + 1 B. - 1 C. No overall charge D. + 2

A

What physical property and reaction type are used by extraction as useful techniques to separate and purify mixtures of compounds? A. Physical property = solubility differences; reaction type = acid-base reaction. B. Physical property = boiling point; reaction type = acid-base reaction. C. Physical property = solubility differences; reaction type = oxidation-reduction. D. Physical property = density; reaction type = oxidation-reduction.

B

What two groups make up the carboxylic acid group (RCOOH)? A. Carbon dioxide and hydrogen B. Carbonyl and hydroxyl C. Carbon monoxide and hydroxyl D. Carbonyl oxide and hydrogen

B

What would happen if a mixture of benzoic acid (C6H5COOH) and NaCl is added to a separatory funnel containing H2O and CH2Cl2? A. The benzoic acid would dissolve in the water layer and the NaCl would dissolve in the organic layer. B. The benzoic acid would dissolve in the organic layer and the NaCl would dissolve in the water layer. C. Both benzoic acid and NaCl would dissolve in the organic layer. D. Both benzoic acid and NaCl would dissolve in the water layer.

C

What would happen if a mixture of benzoic acid and cyclohexanol dissolved in CH2Cl2 is treated with aqueous NaOH solution? A. Benzoic acid would remain in the CH2Cl2 layer, and cyclohexanol would dissolve in the aqueous layer. B. Benzoic acid would dissolve in the aqueous layer while cyclohexanol would remain in the CH2Cl2 layer. C. The salt of benzoic acid would dissolve in the aqueous layer while cyclohexanol would remain in the CH2Cl2 layer. D. The salt of benzoic acid would remain in the CH2Cl2 layer while cyclohexanol would dissolve in the aqueous layer.

C

Which of the following bases are strong enough to significantly deprotonate ethanol, CH3CH2OH (pKa = 16)? A. NaOCH3 B. NaOH C. NaH D. NaOCH2CH3

B

Which of the following cannot be the starting material for the following reaction? A. I B. II C. III D. IV

B

Which of the following compounds is least basic? A. I B. II C. III D. IV

D

Which of the following compounds is most basic? A. I B. II C. III D. IV

D

Which of the following is the correct IUPAC name for the following structure? A. Potassium propanoate B. Butanoic potassium C. Potassium propanoic D. Potassium butanoate

D

Which of the following is the most polar organic compound? A. CH3CH2CH2CH3 B. CH3CH2CHO C. CH3CH2CH2OH D. CH3COOH

D

Which of the following reagents can accomplish the transformation below? A. PCC, CH2Cl2 B. [1] LiAlH4, THF; [2] H2O C. [1] O3; [2] H2O D. K2Cr2O7, H2SO4, H2O

D

Which of the following structures is the major contributor to the resonance hybrid of the phenoxide anion? A. I B. II C. III D. IV

C

Why is pure acetic acid often called glacial acetic acid? A. Because it freezes just below 0°C, forming white crystals. B. Because it freezes just below 100°C, forming white crystals. C. Because it freezes just below room temperature, forming white crystals. D. Because it freezes just above room temperature, forming white crystals.

D

Why is the C-O single bond of a carboxylic acid shorter than the C-O single bond of an alcohol? A. The carbon in the alcohol is sp2 hybridized and has a higher percent s-character that lengthens the C-O bond in the alcohol. B. The carbon in the carboxylic acid is sp3 hybridized and has a lower percent s-character that shortens the C-O bond in the carboxylic acid. C. The carbon in the carboxylic acid is sp hybridized and has a higher percent s-character that shortens the C-O bond in the carboxylic acid. D. The carbon in the carboxylic acid is sp2 hybridized and has a higher percent s-character that shortens the C-O bond in the carboxylic acid.