Mass = 0.44 g
No. of moles = Given Volume/Molar Volume = 112/22400
Molar Mass =  0.44/112 x 22400 = 88g
C_nH_2n+1 + OH = 88
12n+ (1)(2n+1) + 16 +1 = 88
14n + 18 = 88
14n = 88 - 18
n =70/14 = 5

                                                          Pentanoicacid

\(\underset {Phenol} {\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}}+\mathrm{Zn}(\text { dust }) \rightarrow \underset {benzene(A)} {\mathrm{C}_{6} \mathrm{H}_{6}}+\mathrm{ZnO}\)

In this reaction, phenol is first converted into sodium phenoxide which is more reactive than phenol towards electrophilic substitution reaction with CO₂, Treatment of sodium phenoxide with CO₂ at 400 K, 4-7 bar pressure followed by acid hydrolysis gives salicylic acid.

(i) Chloro benzene:
When Chlorobenzene is hydrolysed with 6-8% NaOH at 300 bar and 633K in a closed vessel, sodium phenoxide is formed which on treatment with dilute HCl gives phenol.

(ii) isopropyl benzene:
A mixture of benzene and propene is heated at 523K in a closed vessel in presence of H₃PO₄ catalyst gives cumene (isopropylbenzene). On passing air to a mixture of cumene and 5% aqueous sodium carbonate solution, cumene hydro peroxide is formed by oxidation. It is treated with dilute acid to get phenol and acetone. Acetone is also an important byproduct in this reaction.

\({ CH }_{ 3 }-{ CH }_{ 2 }-OH\overset { { H }_{ 2 }{ SO }_{ 4 } }{ \underset { 443k }{ \longrightarrow } } { CH }_{ 2 }={ CH }_{ 2 }+{ H }_{ 2 }O\)
Mechanism
Primary alcohols undergo dehydration by E₂ mechanism

Tertiary alcohols do not undergo oxidation reaction under normal conditions, but at elevated temperature under strong oxidizing, agent cleavage of C-C-bond takes place to give a mixture of carboxylic acid.

Yes, we can use nucleophiles such as NH₃, CH₃O^- for the nucleophilic substitution of alcohol.
Example
\(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH}+\mathrm{NH}_{3} \rightarrow \mathrm{C}_{2} \mathrm{H}_{5} \mathrm{NH}_{2}+\mathrm{H}_{2} \mathrm{O} \)
\(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH}+\mathrm{CH}_{2} \mathrm{~N}_{2} \rightarrow \mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OCH}_{3}+\mathrm{N}_{2}\)

(i) 2-methyl propan-2-o1 < Butan-2-ol < Butan-1-ol

(ii) propan-2-ol < propan-1-ol < propan -1,3- diol < propan-1,2,3-triol

(i) Acid catalysed hydration

(ii) Hydroboration

(iii) Hydroxylation using Baeyer's reagent

Acetaldehyde - CH₃-CHO

 

 
Since 1 - methoxy propane has primary alkyl group, it under goes SN2 reaction.