Explain the following:

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Solution

$\begin{matrix} C o m p o u n d (A) & C o m p o u n d (B) & C o m p o u n d (C) (i) T h e r e a r e & (i) O n r e d u c t i o n & (i) O n r e d u c t i o n 4 a r o m a t i c & o f c e n t r a l r i n g & o f o n l y o n e b e n z e n e & i n (A), t h e r e & a r o m a t i c o u t e r r i n g s & a r e 3 a r o m a t i c & b e n z e n e r i n g (i i) T h e r e a r e & b e n z e n e & i n A, t h e r e a r e 3 f o u r - & r i n g s l e f t . N o & 3 a r o m a t i c m e m b e r e d & a n t i - a r o m a t i c & b e n z e n e r i n g s a n t i - & r i n g i s l e f t . & l e f t a n d 2 a r o m a t i c & S o i t b e c o m e s & a n t i - a r o m a t i c r i n g s & m o r e s t a b l e . & f o u r - m e m b e r e d S t a b i l i t y o r d e r & r i n g s a r e l e f t i n i s : A r o m a t i c > & (C) s o i t i s l e s s n o n - a r o m a t i c > & s t a b l e t h a n (B) a n t i a r o m a t i c \end{matrix}$
Hence from reduction of (A) by use of moles of H_2/catalyst, (B) is formed not (C).

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