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Question
Write the isomers of the compound having the formula C4H9Br.
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Solution
C4H9Br is a saturated compound because its parent hydrocarbon is C4H10.
Its isomers are as follows:
(i) \[\ce{\underset{1-Bromobutane}{CH3 - CH2 - CH2 - CH2 - Br}}\]
(ii) \[\begin{array}{cc}
\phantom{.........}\ce{Br}\\
\phantom{.......}|\\
\ce{\underset{2-Bromobutane}{CH3-CH2-CH-CH3}}
\end{array}\]
(iii) \[\begin{array}{cc}
\ce{CH3}\phantom{...}\\
|\phantom{......}\\
\ce{\underset{1-Bromo-2-Methylpropane}{CH3-CH-CH2Br}}
\end{array}\]
(iv) \[\begin{array}{cc}
\phantom{..}\ce{CH3}\\
|\phantom{..}\\
\ce{CH3 - C - Br}\phantom{.....}\\
|\phantom{..}\\
\phantom{..}\ce{\underset{2-Bromo-2-Methylpropane}{CH3}}
\end{array}\]
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| I | II | III | IV |
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Nucleophilic Substitution: Influences of solvent polarity: The reaction rate (SN2) of 2-bromopropane and NaOH in ethanol containing 40% water is twice slower than in absolute ethanol. Hence the level of solvent polarity has an influence on both SN1 and SN2 reactions but with different results. Generally speaking, a weak polar solvent is favourable for SN2 reaction, while a strong polar solvent is favourable for SN1. Generally speaking, the substitution reaction of tertiary haloalkane is based on SN1 mechanism in solvents with a strong polarity (for example ethanol containing water). |
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(ii)

OR
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(i) \[\begin{array}{cc}
\phantom{}\ce{\underset{}{(CH3)2CH - CH2Br} ->[C2H5OH] \underset{}{(CH3)2CH - CH2OC2H5 + HBr}}\\
\end{array}\]
(ii) \[\begin{array}{cc}
\phantom{}\ce{\underset{}{(CH3)2CH - CH2Br} ->[C2H5O-] \underset{}{(CH3)2CH - CH2OC2H5 + Br-}}\\
\end{array}\]
The mechanisms of reactions (i) and (ii) are respectively:




