91Ó°ÊÓ

Which of the following bases are strong enough to cause essentially complete deprotonation of methanol? The \(\mathrm{p} K_{\mathrm{a}}\) of the conjugate acid is given in parentheses. (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Li}(50)\); (b) \(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{Na}(4.7)\); (c) LiN[CH(CH \(\left._{3}\right)_{2} /_{2}\) (LDA, 40 ); (d) \(\mathrm{KH}(38) ;\) (e) \(\mathrm{CH}_{3} \mathrm{SNa}(10)\).

Rank each group of compounds in order of increasing boiling point. (a) Cyclohexane, cyclohexanol, chlorocyclohexane; (b) 2,3 -dimethyl-2-pentanol, 2-methyl-2-hexanol, 2 -heptanol.

Explain the order of water solubilities for the compounds in each of the following groups. (a) Ethanol > chloroethane \(>\) ethane; (b) methanol \(>\) ethanol \(>1\) -propanol.

Rank the compounds in each group in onder of decreasing acidity. (a) \(\mathrm{CH}_{3} \mathrm{CHClCH}_{2} \mathrm{OH}, \mathrm{CH}_{3} \mathrm{CHBrCH}_{2} \mathrm{OH}, \mathrm{BrCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\) (b) \(\mathrm{CH}_{3} \mathrm{CCl}_{2} \mathrm{CH}_{2} \mathrm{OH}, \mathrm{CCl}_{3} \mathrm{CH}_{2} \mathrm{OH},\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CClCH}_{2} \mathrm{OH}\) (c) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHOH},\left(\mathrm{CF}_{3}\right)_{2} \mathrm{CHOH},\left(\mathrm{CCl}_{3}\right)_{2} \mathrm{CHOH}\)

Suggest the best synthetic route to each of the following simple alcohols, using in each case a simple alkane as your initial starting molecule. What are some disadvantages of beginning syntheses with alkanes? (a) Methanol (b) Ethanol (c) 1-Propanol (d) 2-Propanol (e) 1-Butanol (f) 2-Butanol (g) 2-Methyl-2-propanol

Devise three different syntheses of 3 -octanol starting with (a) a ketone; (b) an aldehyde; (c) an aldehyde different from that employed in (b).