Question

Draw the products formed when propan-2-ol $\left[{\left({\mathrm{CH}}_3\right)}_2\mathrm{CHOH}\right]$ the main ingredient in rubbing alcohol, is treated with each acid or base: a. NaH b.${\mathbf{H}}_{\mathbf{2}}{\mathbf{SO}}_{\mathbf{4}}$ c.${\mathbf{Li}}^{\mathbf{+}}\mathbf{-}\mathbf{N}{\left[\mathrm{CH}{\left({\mathrm{CH}}_3\right)}_2\right]}_{\mathbf{2}}$ d. ${\mathbf{CH}}_{\mathbf{3}}{\mathbf{CO}}_{\mathbf{2}}\mathbf{H}$

Short answer

a.

b.

c.

d.

Step-by-step solution

Conjugate acid and conjugate bases

Conjugate acids and bases are obtained in two ways:

• When a base abstract a proton
• When an acid releases its proton

Properties of propane-2-ol

Propane-2-ol can behave as an acid as well as abase. In the reaction of propane-2-ol with an acid, it acts as a base, and vice versa.

Formation of conjugate acids and bases

a. NaH is a base. Here, propane-2-ol behaves as acid and form its conjugate acid and conjugate base as shown below:

Representation of conjugate acid and base of a

b. ${\mathrm{H}}_2{\mathrm{SO}}_4$is an acid. Here, propane-2-ol behaves as a base and forms its conjugate acid and conjugate base as shown below:

Representation of conjugate acid and base of b

c.${\mathrm{Li}}^{+}-\mathrm{N}{\left[\mathrm{CH}{\left({\mathrm{CH}}_3\right)}_2\right]}_2$is a base. Here, propane-2-ol behaves as acid and forms its conjugate acid and conjugate base as shown below:

Representation of conjugate acid and base of c

d. ${\mathrm{CH}}_3{\mathrm{CO}}_2\mathrm{H}$is an acid. Here, propane-2-ol behaves as a base and forms its conjugate acid and conjugate base as shown below:

Representation of conjugate acid and base