Exam 8: Nomenclature and Noncovalent Intermolecular Interactions

When two hydrocarbon molecules (such as hexane), initially dissolved in water, come together to form an aggregate in water, two of the following are true.

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Question 1

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D, E

This is the predominant form of the sugar D-glucose. Glucose does not passively cross cell membranes, even though it is a neutral molecule. Explain why.

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The cell membrane consists of a lipid bilayer, where the outside of the layer contains the hydrophilic head groups and the inner portion contains the hydrophobic tails. In order to pass through the cell membrane through passive diffusion, the molecule must not be insoluble in hydrocarbons, nor highly soluble in hydrocarbons. Small neutral molecules like molecular oxygen can pass through, but glucose is a much larger molecule. While it contains six carbon atoms, it also contains five hydrophilic hydroxy groups that will not be able to pass through the hydrocarbon tails. In the body, glucose requires carrier proteins that help it to cross cell membranes.

The boiling point of pentane is 36 °C. The compound with the highest boiling point is

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Question 3

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In each case, identify the better solvent for dissolving the compounds. Choose between H₂O (ε = 78) or benzene (ε = 2.3). (Benzene is a six-carbon cyclic hydrocarbon.)

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Question 4

In which solvent should NaCl (an ionic compound) have the greatest solubility? (ε = dielectric constant.) Explain your choice briefly.

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Question 5

Sodium chloride, an ionic compound, should be most soluble in which solvent? ( = dielectric constant) (a) hexane $( \epsilon = 2 )$ (b) $Sodium chloride, an ionic compound, should be most soluble in which solvent? ( = dielectric constant) (a) hexane ( \epsilon = 2 ) (b) acetone ( \epsilon = 19 ) (c) N -methylpyrrolidone ( \epsilon = 32 ) (d) \text { N., } \text {-dimethylformamide }(\epsilon=37) (e) dimethylsulfoxide ( \epsilon = 47 )$ acetone $( \epsilon = 19 )$ (c) $Sodium chloride, an ionic compound, should be most soluble in which solvent? ( = dielectric constant) (a) hexane ( \epsilon = 2 ) (b) acetone ( \epsilon = 19 ) (c) N -methylpyrrolidone ( \epsilon = 32 ) (d) \text { N., } \text {-dimethylformamide }(\epsilon=37) (e) dimethylsulfoxide ( \epsilon = 47 )$ $N$ -methylpyrrolidone $( \epsilon = 32 )$ (d) $Sodium chloride, an ionic compound, should be most soluble in which solvent? ( = dielectric constant) (a) hexane ( \epsilon = 2 ) (b) acetone ( \epsilon = 19 ) (c) N -methylpyrrolidone ( \epsilon = 32 ) (d) \text { N., } \text {-dimethylformamide }(\epsilon=37) (e) dimethylsulfoxide ( \epsilon = 47 )$ $\text { N., } \text {-dimethylformamide }(\epsilon=37)$ (e) $Sodium chloride, an ionic compound, should be most soluble in which solvent? ( = dielectric constant) (a) hexane ( \epsilon = 2 ) (b) acetone ( \epsilon = 19 ) (c) N -methylpyrrolidone ( \epsilon = 32 ) (d) \text { N., } \text {-dimethylformamide }(\epsilon=37) (e) dimethylsulfoxide ( \epsilon = 47 )$ dimethylsulfoxide $( \epsilon = 47 )$

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Question 6

Dissolving hexane in water has

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Question 7

Draw the structure of 3-hexyn-2-ol.

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Question 8

Name the compound. Include the appropriate stereochemical designation in the name.

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Question 9

Consider the equilibria in CCl₄, an apolar, aprotic, nondonor solvent. Explain why replacing the two carbons of the ring shown above with oxygens makes the axial conformation more stable.

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Question 10

Draw all the alcohols having a molecular formula of C₄H₁₀O. a. Indicate if the alcohol is chiral. b. Name each alcohol using IUPAC nomenclature. c. Classify each alcohol as primary, secondary or tertiary.

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Question 11

When DMSO dissolves potassium chloride (K⁺ Cl⁻), what is the solvation of the salt due to?

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Question 12

Drugs are often conjugated to glucuronic acid groups in biological systems. Explain why you would need to conjugate a drug to glucuronic acid and how glucuronides solve this problem.

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Question 13

Name the compound with an IUPAC systematic name.

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Question 14

Arrange these compounds in order of increasing boiling point (lowest boiling point first).

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Question 15

Draw the structure of 3-ethoxy-2-butanethiol (alternate name 3-ethoxybutane-2-thiol).

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Question 16

Which compound would form the strongest complex with potassium ion?

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Question 17

Select the structure of the compound with the highest boiling point. (a) $\mathrm{Cl}-\mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2}-\mathrm{Cl}$ (b) $\mathrm { Cl } - \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { Cl }$ (c) $\mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { OH }$ (d) $Select the structure of the compound with the highest boiling point. (a) \mathrm{Cl}-\mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2}-\mathrm{Cl} (b) \mathrm { Cl } - \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { Cl } (c) \mathrm { CH } _ { 3 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } \mathrm { CH } _ { 2 } - \mathrm { OH } (d)$

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Question 18

Provide a systematic name for the compound, including any stereochemical designations.

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Question 19

By circling three items below each structure, classify each of the following solvents as polar or apolar, donor or nondonor, protic or aprotic. $By circling three items below each structure, classify each of the following solvents as polar or apolar, donor or nondonor, protic or aprotic. \begin{array}{c} \begin{array}{lc} \text { polar } & \text { apolar } \\ \text { donor } & \text { nondonor } \\ \text { protic } & \text { aprotic } \end{array} \begin{array}{ll} \text { polar } & \text { apolar } \\ \text { donor } & \text { nondonor } \\ \text { protic } & \text { aprotic } \end{array} \end{array}$ $By circling three items below each structure, classify each of the following solvents as polar or apolar, donor or nondonor, protic or aprotic. \begin{array}{c} \begin{array}{lc} \text { polar } & \text { apolar } \\ \text { donor } & \text { nondonor } \\ \text { protic } & \text { aprotic } \end{array} \begin{array}{ll} \text { polar } & \text { apolar } \\ \text { donor } & \text { nondonor } \\ \text { protic } & \text { aprotic } \end{array} \end{array}$ polar apolar donor nondonor protic aprotic polar apolar donor nondonor protic aprotic

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Question 20

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Exam 8: Nomenclature and Noncovalent Intermolecular Interactions

When two hydrocarbon molecules (such as hexane), initially dissolved in water, come together to form an aggregate in water, two of the following are true.

This is the predominant form of the sugar D-glucose. Glucose does not passively cross cell membranes, even though it is a neutral molecule. Explain why.

The boiling point of pentane is 36 °C. The compound with the highest boiling point is

In each case, identify the better solvent for dissolving the compounds. Choose between H2O (ε = 78) or benzene (ε = 2.3). (Benzene is a six-carbon cyclic hydrocarbon.)

In which solvent should NaCl (an ionic compound) have the greatest solubility? (ε = dielectric constant.) Explain your choice briefly.

Dissolving hexane in water has

Draw the structure of 3-hexyn-2-ol.

Name the compound. Include the appropriate stereochemical designation in the name.

Consider the equilibria in CCl4, an apolar, aprotic, nondonor solvent. Explain why replacing the two carbons of the ring shown above with oxygens makes the axial conformation more stable.

Draw all the alcohols having a molecular formula of C4H10O. a. Indicate if the alcohol is chiral. b. Name each alcohol using IUPAC nomenclature. c. Classify each alcohol as primary, secondary or tertiary.

When DMSO dissolves potassium chloride (K+ Cl−), what is the solvation of the salt due to?

Drugs are often conjugated to glucuronic acid groups in biological systems. Explain why you would need to conjugate a drug to glucuronic acid and how glucuronides solve this problem.

Name the compound with an IUPAC systematic name.

Arrange these compounds in order of increasing boiling point (lowest boiling point first).

Draw the structure of 3-ethoxy-2-butanethiol (alternate name 3-ethoxybutane-2-thiol).

Which compound would form the strongest complex with potassium ion?

Provide a systematic name for the compound, including any stereochemical designations.

By circling three items below each structure, classify each of the following solvents as polar or apolar, donor or nondonor, protic or aprotic. polar apolar donor nondonor protic aprotic polar apolar donor nondonor protic aprotic

Chemical Bonding and Chemical Structure

Alkanes and Organic Nomenclature

The Curved-Arrow Notation, Resonance, Acids and Bases, and Chemical Equilibrium

Introduction to Alkenes and Alkynes

Addition Reactions of Alkenes and Alkynes

Principles of Stereochemistry

Cyclic Compounds and Reaction Stereochemistry

The Chemistry of Alkyl Halides

Free-Radical Reactions, Main-Group Organometallic Compounds, and Carbenes

The Chemistry of Alcohols and Thiols

The Chemistry of Ethers, Epoxides, Glycols, and Sulfides

Introduction to Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Dienes and Aromaticity

The Chemistry of Benzene and Its Derivatives

Allylic and Benzylic Reactivity

The Chemistry of Aryl Halides, Vinylic Halides, and Phenols

The Chemistry of Aldehydes and Ketones

The Chemistry of Carboxylic Acids

The Chemistry of Carboxylic Acid Derivatives

The Chemistry of Enolate Ions, Enols, and Α,β-Unsaturated Carbonyl Compounds

The Chemistry of Amines

Carbohydrates

The Chemistry of Thioesters, Phosphate Esters, and Phosphate Anhydrides

The Chemistry of the Aromatic Heterocycles and Nucleic Acids

Amino Acids, Peptides, and Proteins

Pericyclic Reactions

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In each case, identify the better solvent for dissolving the compounds. Choose between H₂O (ε = 78) or benzene (ε = 2.3). (Benzene is a six-carbon cyclic hydrocarbon.)

Consider the equilibria in CCl₄, an apolar, aprotic, nondonor solvent. Explain why replacing the two carbons of the ring shown above with oxygens makes the axial conformation more stable.

Draw all the alcohols having a molecular formula of C₄H₁₀O. a. Indicate if the alcohol is chiral. b. Name each alcohol using IUPAC nomenclature. c. Classify each alcohol as primary, secondary or tertiary.

When DMSO dissolves potassium chloride (K⁺ Cl⁻), what is the solvation of the salt due to?