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Nomenclature of Alcohols

Which is more...

Question

Which is more stable and why?
NO₂ CH₂ CH₂ O^- or CH₃ CH₂ CH₂ O^-

3,3-dimethyl-1-butene or 3-methly-1-pentene

CH₃CH₂⁺ or (CH₃)₂ CH⁺

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Solution

$1 . N O_{2} C H_{2} C H_{2} O^{-} o r C H_{3} C H_{2} C H_{2} O^{-} . T h e m o s t s t a b l e i s t h e o n e w i t h e l e c t r o n w i t h d r a w i n g g r o u p . E l e c t r o n w i t h d r a w i n g g r o u p s t a b i l i s e s t h e a n i o n m o r e a s i t w i t h d r a w s t h e e l e c t r o n t o w a r d s i t s e l f . S o t h e s t a b l e o n e i s N O_{2} C H_{2} C H_{2} O^{-} a s i t s h a v i n g e l e c t r o n w i t h d r a w i n g N O_{2} g r o u p, t h e o t h e r o n e i s h a v i n g e l e c t r o n r e l e a s i n g C H_{3} g r o u p, w h i c h d e s t a b i l i s e s t h e n e g a t i v e c h a r g e 2 . C H_{2} = C H - C (C H_{3})_{2} - C H_{3} o r C H_{2} = C H - C H (C H_{3}) - C H_{2} - C H_{3} 3, 3 - d i m e t h y l 1 - b u t e n e i s m o r e s t a b l e a s i t s h a v i n g m o r e b r a n c h i n g a n d t e r t i a r y c a r b o n . T h e o t h e r c o m p o u n d 3 - m e t h y l - 1 - p e n t e n e i s h a v i n g s e c o n d a r y c a r b o n o n l y . 3 . S e c o n d a r y c a r b o c a t i o n i s m o s t s t a b l e t h a n t h e p r i m a r y . S o (C H_{3})_{2} C H^{+} i s m o r e s t a b l e t h a n t h e C H_{3} C {H_{2}}^{+}$

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Q. In which of the following pairs of carbocations, the first carbocation is more stable than the second?

C H_{2} = C H - + C H_{2} and C H_{2} = C H - C H_{2} - + C H_{2}

C H_{3} - N H - + C H_{2} and + C H_{2} - O H

C H_{3} - O - C H_{2} - + C H_{2} and C H_{2} - O - + C H_{2}

C H_{3} - + C H - C H_{2} C H_{2} C H_{3} and C H_{3} C H_{2} - + C H - C H_{2} C H_{3}

Q. Out of which

N O_{2} - C H_{2} - C H_{2} - O^{⊖}

C H_{3} - C H_{2} - C H_{2} - O^{⊖}

which one is more stable and why?

Consider the following statements :

C H_{3} O \oplus C H_{2}

is more stable than

C H_{3} \oplus C H_{2}

{M e}_{2} \oplus C H

is more stable than

C H_{3} C H_{2} \oplus C H_{2}

C H_{2} = C H - \oplus C H_{2}

is more stable than

C H_{3} C H_{2} \oplus C H_{2}

C H_{2} = \oplus C H

is more stable than

C H_{3} \oplus C H_{2}

Out of these statements :

Q. Arrange the following in increasing order of boiling point:
(i)

C H_{3} - C H_{2} - C H_{2} - C H_{2} - B r

(C H_{3})_{2} - C H - C H_{2} - B r

(C H_{3})_{2} - C H - B r

Q. Which of the following lone-pair indicated is not involved in resonance?
(A)

C H_{2} = C H - . . N H - C H_{3}

C H_{2} = C H - . . O . . - C H_{3}

C H_{2} = C H - . . O . . - C H = C H_{2}

C H_{2} = C H - N H_{2}

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