Chapter 9, Problem 37P

Answer each question using the ball-and-stick model of compound A.

a. Give the IUPAC name for A, including $R,S$ designations f or stereogenic centers.

b. Classify A as a $1^{\text{ο}},2^{\text{ο}},\text{or}{3}^{\text{ο}}$ alcohol.

c. Draw a stereoisomer for A and give its IUPAC name.

d. Draw a constitutional isomer that contains an $\text{OH}$ group and give its IUPAC name.

e. Draw a constitutional isomer that contains an ether and give its IUPAC name.

f. Draw the products formed (including stereochemistry) when A is treated with each reagent: $\left[1\right]$ $\text{NaH}$; $\left[2\right]$ ${\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$; $\left[3\right]$ ${\text{POCl}}_{\text{3}}$, pyridine; $\left[4\right]$ $\text{HCl}$; $\left[5\right]$ ${\text{SOCl}}_{\text{2}}$, pyridine; $\left[6\right]$ $\text{TsCl}$, pyridine.