Chapter 16, Problem 25P

Write the structure of the principal organic product formed in the reaction of $1$-propanol with each of the following reagents:

Sulfuric acid (catalytic amount), heat at $140$

°C

Sulfuric acid (catalytic amount), heat at $200$

°C

Dimethyl sulfoxide (DMSO), oxalyl chloride $\left[{\left(\text{COCl}\right)}_{\text{2}}\right]$, trimethylamine $\left[\text{N}{\left({\text{CH}}_{\text{2}}{\text{CH}}_{\text{3}}\right)}_{\text{3}}\right]$

Pyridinium chlorochromate (PCC) in dichloromethane

Potassium dichromate $\left({\text{K}}_{\text{2}}{\text{Cr}}_{\text{2}}{\text{O}}_{\text{7}}\right)$ in aqueous sulfuric acid, heat sodium amide $\left({\text{NaNH}}_{\text{2}}\right)$

Acetic acid in the presence of dissolved hydrogen chloride

in the presence of pyridine

in the presence of pyridine

in the presence of pyridine

in presence of pyridine