Reaction of Alcohols with Phosohorus Halides

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. 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. Organometalics and alkyl halides will likely be used.

Q. Select the correct options with respect to the reaction of cis-3-methylcyclopentanol with $P/I_2$:

1. The reaction is $S_{N}1$
2. The reaction is $S_{N}2$
3. The substrate is optically active
4. The product is optically active

Q. Select the correct options with respect to the reaction of cis-3-methylcyclopentanol with $PB{r}_3$:

1. The reaction is $S_{N}2$
2. The reaction is $S_{N}1$
3. The product is optically active
4. The product is racemic

Q. In the following reaction sequence, the correct structure(s) of X is/are:

1. 
2. 
3. 
4. 

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 product formed on reaction of ethyl alcohol with bleaching Powder is

1. $CHC{l}_3$
2. $C{H}_{3}COC{H}_3$
3. $CC{l}_{3}CHO$
4. $C{H}_{3}CHO$

Q. Compound 'A' reacts with $PC{l}_5$ to give 'B' which on treatment with KCN followed by hydrolysis gave propanoic acid as the product. What is 'A'?

1. Propane
2. Ethyl chloride
3. Ethane
4. Ethyl alcohol

Q. The final product obtained by distilling ethyl alcohol with the excess of chlorine and $Ca(OH{)}_2$ is

1. $C{H}_{3}CHO$
2. $CC{l}_{3}CHO$
3. $CHC{l}_3$
4. $(C{H}_3{)}_{2}O$

Q. Ethanol when reacted with $PC{l}_5$ gives (A), $POC{l}_3$ and $HCl$. (A) reacts with silver nitrite to form (B) (major product) and $AgCl$. (A) and (B) are respectively.

1. $C_2{H}_6$ and $C_2{H}_{5}O{C}_2{H}_5$
2. $C_2{H}_{5}Cl$ and $C_2{H}_{5}N{O}_2$
3. $C_2{H}_6$ and $C_2{H}_{5}N{O}_2$
4. $C_2{H}_{5}Cl$ and $C_2{H}_{5}O{C}_2{H}_5$