Reaction of Alcohols with Phosohorus Halides

Q. The compound A on treatment with $Na$ gives B, and with $PC{l}_5$ gives C. B and C react together to give diethyl ether. A, B and C are in the order :

1. $C_2{H}_{5}Cl$, $C_2{H}_6$, $C_2{H}_{5}OH$
2. $C_2{H}_{5}OH$, $C_2{H}_{5}Cl$, $C_2{H}_{5}ONa$
3. $C_2{H}_{5}OH$, $C_2{H}_6$, $C_2{H}_{5}Cl$
4. $C_2{H}_{5}OH$, $C_2{H}_{5}ONa$, $C_2{H}_{5}Cl$

Q. The products for the following reaction will be:

$3C_2{H}_{5}OH+PC{l}_3\stackrel{\text{Pyridine}}{\to }\text{Products}$

1. $3C{H}_{3}OH+PCl$
2. $3C_2{H}_{5}Cl+H_{3}P{O}_3$
3. $C_6{H}_{14}+H_{3}P{O}_3$
4. None of the above

Q. Assume common laboratory reagents and chemicals are available. Starting with cyclopentanol and any other alcohol(s) each having not more than 4 carbons, synthesize:

1. One of steps will involve the formation of Carbon-Carbon sigma bond
2. One of steps must involve the formation of Carbon-Carbon pi bond
3. One of the steps involve addition across the carbonyl pi bond
4. Organometallics and alkyl halides will likely be used

Q. $n-Propylchloride\stackrel{alcKCN}{\to }\left(P\right)\stackrel{H_3{O}^{+}}{\to }\left(Q\right)$
Which statement is not true about the compounds P and Q?

1. P on reduction gives butanamine
2. Q is butanoic acid
3. Q on decarboxylation gives propane
4. P is propanenitrile