91Ó°ÊÓ

Draw the structure of an alkyl bromide with molecular formula \(\mathrm{C}_{6} \mathrm{H}_{13} \mathrm{Br}\) that fits each description: (a) a \(1^{\circ}\) alkyl bromide with one stereogenic center; (b) a \(2^{\circ}\) alkyl bromide with two stereogenic centers; (c) an achiral \(3^{\circ}\) alkyl bromide.

Give the structure corresponding to each name. a. 3-chloro-2-methylhexane b. 4-ethyl-5-iodo-2,2-dimethyloctane c. cis-1,3-dichlorocyclopentane d. \(1,1,3\) -tribromocyclohexane e. propyl chloride f. sec-butyl bromide

Rank the compounds in each group in order of increasing boiling point. a. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{I}, \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Cl}, \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{~F}\) b. \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{4} \mathrm{CH}_{3}, \mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{5} \mathrm{Br}, \mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{5} \mathrm{OH}\)

Draw the product of nucleophilic substitution with each neutral nucleophile. When the initial substitution product can lose a proton to form a neutral product, draw that product as well. a. b. \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{Cl}+\mathrm{H}_{2} \ddot{\mathrm{O}}: \longrightarrow\)

Which is the better leaving group in each pair? a. \(\mathrm{Cl}^{-}, \mathrm{I}^{-}\) b. \(\mathrm{NH}_{3},{ }^{-} \mathrm{NH}_{2}\) c. \(\mathrm{H}_{2} \mathrm{O}, \mathrm{H}_{2} \mathrm{~S}\)

Which molecules contain good leaving groups? a. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}\) b. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\) c. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \stackrel{+}{\mathrm{O}} \mathrm{H}_{2}\) d. \(\mathrm{CH}_{3} \mathrm{CH}_{3}\)

Should it be possible to convert \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\) to \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Cl}\) by a nucleophilic substitution reaction with \(\mathrm{NaCl}\) ? Explain why or why not.

Identify the stronger nucleophile in each pair. a. \(\mathrm{NH}_{3},{ }^{-} \mathrm{NH}_{2}\) b. \(\mathrm{CH}_{3}^{-}, \mathrm{HO}^{-}\) c. \(\mathrm{CH}_{3} \mathrm{NH}_{2}, \mathrm{CH}_{3} \mathrm{OH}\) d. \(\mathrm{CH}_{3} \mathrm{COO}^{-}, \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{O}^{-}\)

Classify each solvent as protic or aprotic. a. \(\mathrm{HOCH}_{2} \mathrm{CH}_{2} \mathrm{OH}\) b. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCH}_{2} \mathrm{CH}_{3}\) c. \(\mathrm{CH}_{3} \mathrm{COOCH}_{2} \mathrm{CH}_{3}\)

Identify the stronger nucleophile in each pair of anions. a. \(\mathrm{Br}^{-}\) or \(\mathrm{Cl}^{-}\) in a polar protic solvent b. \(\mathrm{HO}^{-}\) or \(\mathrm{Cl}^{-}\) in a polar aprotic solvent c. \(\mathrm{HS}^{-}\) or \(\mathrm{F}^{-}\) in a polar protic solvent