I-iodopropane undergoes faster e2 elemination than i-chloropropane .Explain
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2-Chloropropane will undergo substitution faster than 1-chloro-2,2-dimethylpropane.
The acetylide anion, HC≡C⁻, is the conjugate base of the extremely weak acid, acetylene.
So it is both a powerful nucleophile and an extremely strong base — about a billion times as strong as hydroxide ion.
It undergoes
S
N
2
reactions with methyl and primary alkyl halides.
But acetylide ion is such a strong base that it undergoes mainly
E2
eliminations with 2° alkyl halides.
And it undergoes only
E2
elimination with 3° alkyl halides.
An
S
N
2
reaction goes by backside attack at the α carbon atom.
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