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Exam 8: Nomenclature and Noncovalent Intermolecular Interactions

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Question 1

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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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benzene; w...

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Question 2

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

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(4S,5R)-5-...

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Question 3

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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.

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

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

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

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

Which compound would form the strongest complex with potassium ion?

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.

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 $( \epsilon = 47 )$

Dissolving hexane in water has

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.

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

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

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)

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

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.

Name the compound with an IUPAC systematic name.

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

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.