OH group in phenols is a strong electron donating group. As a result, electron density on the benzene ring is quite high and hence it repeles nucleophiles. In other words nucleophiles cannot attack the benzene ring and hence phenol usually do not give nucleophiles. In other words, nucleophiles cannot attack the benzene ring and hence phenols usually do not hive nucleophilic substitution reactions.

The OH group in phenol is more strongly held because of double bond character between C and O due to resonance.

\(\underset { (i) }{ { C }H_{ 3 }{ C }H_{ 2 }{ C }H_{ 2 }{ C }H_{ 2 }OH } \ \ \underset { (ii) }{ { C }H_{ 3 }{ C }H_{ 2 }\underset { \overset { | }{ OH } }{ C } H{ C }H_{ 3 } } ,\\ \underset { (iii) }{ { C }H_{ 2 }-\underset { \overset { | }{ OH } }{ C } H{ C }H_{ 2 }OH, } \underset { (iv) }{ \quad { C }H_{ 3 }-\overset { \underset { | }{ { C }H_{ 3 } } }{ \underset { \overset { | }{ { C }H_{ 3 } } }{ C } } \ -OH } \)
  (ii) is optically active

\({ C }H_{ 3 }-\underset { \overset { \parallel }{ O } }{ C } -{ C }H_{ 3 }+{ C }H_{ 3 }MgBr\overset { Dry }{ \underset { ether }{ \longrightarrow } } \\ \quad \quad \quad \quad \quad \quad \quad \quad \quad \\ { C }H_{ 3 }-\overset { \underset { | }{ { C }H_{ 3 } } }{ \underset { \overset { | }{ { C }H_{ 3 } } }{ C } } \quad -OMgBr\overset { { H }^{ + }{ H }_{ 2 }O }{ \longrightarrow } \underset { tert-butyl\quad alcohol }{ \quad { C }H_{ 3 }-\overset { \underset { | }{ { C }H_{ 3 } } }{ \underset { \overset { | }{ { C }H_{ 3 } } }{ C } } \quad -OH } \)

Invertase and zymase

\({ C }H_{ 12 }H_{ 22 }O_{ 11 }\overset { Invertase }{ \longrightarrow } \underset { Glucose }{ { C }_{ 6 }H_{ 12 }O_{ 6 } } +\underset { Fructose }{ { C }_{ 6 }H_{ 12 }O_{ 6 } } \) 
\(\\ \underset { Glucose }{ { C }_{ 6 }H_{ 12 }O_{ 6 } } \overset { Invertase }{ \longrightarrow } \underset { Ethanol }{ { 2C }_{ 2 }H_{ 5 }OH } +2CO_{ 2 }\)
or Fructose