Reactions of Haloalkanes

Hydrolysis (Substitution)

Replace X (e.g. Br) with OH

$\mathrm{R}-\mathrm{X}+\mathrm{NaOH}\underset{\mathrm{heat}}{\overset{\mathrm{reflux}}{\to }}\mathrm{R}-\mathrm{OH}+\mathrm{NaBr}$

e.g. $\mathrm{CH}{\phantom{A}}_3-\mathrm{CH}{\phantom{A}}_2-\mathrm{CH}{\phantom{A}}_2-\mathrm{CH}{\phantom{A}}_2-\mathrm{Br}+\mathrm{OH}\underset{\mathrm{heat}}{\overset{\mathrm{reflux}}{\to }}\mathrm{CH}{\phantom{A}}_3-\mathrm{CH}{\phantom{A}}_2-\mathrm{CH}{\phantom{A}}_2-\mathrm{CH}{\phantom{A}}_2-\mathrm{OH}+\mathrm{Br}{\phantom{A}}^{-}$

Br-C-C-C-C
O-C-C-C-C

Reactions of Alcohols

Substitution with halides (Cl/Br/I)

Replace OH with X

$\mathrm{R}-\mathrm{OH}+\mathrm{HX}\stackrel{\mathrm{reflux}}{\to }\mathrm{R}-\mathrm{X}+\mathrm{H}{\phantom{A}}_2\mathrm{O}$

$3\mathrm{R}-\mathrm{OH}+\mathrm{PX}{\phantom{A}}_3\stackrel{\mathrm{reflux}}{\to }3\mathrm{R}-\mathrm{X}+\mathrm{H}{\phantom{A}}_3\mathrm{PO}{\phantom{A}}_3$

e.g. $\mathrm{CH}{\phantom{A}}_3\mathrm{CH}{\phantom{A}}_2-\mathrm{OH}+\mathrm{HCl}\stackrel{\mathrm{reflux}}{\to }\mathrm{CH}{\phantom{A}}_3\mathrm{ClH}{\phantom{A}}_2-\mathrm{Cl}+\mathrm{H}{\phantom{A}}_2\mathrm{O}$

Dehydration (Elimination of Water)

Removes $\mathrm{H}+\mathrm{OH}$

$\mathrm{CH}{\phantom{A}}_3\mathrm{CH}{\phantom{A}}_2\mathrm{OH}\underset{\mathrm{heat}}{\overset{\mathrm{strong}\mathrm{acid}}{\to }}⟶\mathrm{CH}{\phantom{A}}_2=\mathrm{CH}{\phantom{A}}_2+\mathrm{H}{\phantom{A}}_2\mathrm{O}$

O-C-C
C=C

Oxidation

Primary (1${}^{\circ }$ alcohols)

$\mathrm{C}(\mathrm{R})(\mathrm{OH})(\mathrm{H})(\mathrm{H})\stackrel{\mathrm{O}}{\to }\mathrm{C}=\mathrm{O}(\mathrm{R})(\mathrm{H})\stackrel{\mathrm{O}}{\to }\mathrm{C}=\mathrm{O}(\mathrm{R})(\mathrm{OH})$

O-CC
C=O CC

Primary (2${}^{\circ }$ alcohols)

$\mathrm{C}(\mathrm{R})(\mathrm{OH})(\mathrm{R})(\mathrm{H})\stackrel{\mathrm{O}}{\to }\mathrm{C}=\mathrm{O}(\mathrm{R})(\mathrm{H})$ -> Resist Oxidation

Primary (3${}^{\circ }$ alcohols)

$\mathrm{C}(\mathrm{R})(\mathrm{OH})(\mathrm{R})(\mathrm{H})$ -> Resist Oxidation