Explain the reaction and reactivity of halides tested towards silver ion in Sy1 reaction: o Arrange the halides tested in order of decreasing reactivity towards silver ion in SN1 reaction o Explain the order of reactivity observed for the three saturated alkyl halides with silver ion o Explain the unusual reactivity of allyl chloride, while being a primary halide Account for the low reactivity of chlorobenzene towards silver jon

Organic Chemistry
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ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution
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Explain the reaction and reactivity of halides tested towards silver ion in Sy1
reaction:
o Arrange the halides tested in order of decreasing reactivity towards silver ion in
SN1 reaction
o Explain the order of reactivity observed for the three saturated alkyl halides with
silver ion
o Explain the unusual reactivity of allyl chloride, while being a primary halide
o Account for the low reactivity of chlorobenzene towards silver ion
Transcribed Image Text:Explain the reaction and reactivity of halides tested towards silver ion in Sy1 reaction: o Arrange the halides tested in order of decreasing reactivity towards silver ion in SN1 reaction o Explain the order of reactivity observed for the three saturated alkyl halides with silver ion o Explain the unusual reactivity of allyl chloride, while being a primary halide o Account for the low reactivity of chlorobenzene towards silver ion
SN1 Reaction
Nitrate ion acts as a nucleophile towards the alkyl halide, it will substitute the halide.
The product will be a racemic mixture, with 50% of the alkyl nitrate with R
stereochemistry and 50% with S stereochemistry.
Alkyl chlorides yield a visible silver chloride precipitate, which is insoluble in ethanol
and thus provides a signal that a reaction has occurred.
CH3CH2
CH;CH2
ethanol
+ Ag NO,
C+
H CH,
slow
H CH
a
NO:
(X= CI, Br or I)
CH,CH3
CH;CH,
O2NO-
ONO2
H;C H
H CH3
(R)
(S)
Transcribed Image Text:SN1 Reaction Nitrate ion acts as a nucleophile towards the alkyl halide, it will substitute the halide. The product will be a racemic mixture, with 50% of the alkyl nitrate with R stereochemistry and 50% with S stereochemistry. Alkyl chlorides yield a visible silver chloride precipitate, which is insoluble in ethanol and thus provides a signal that a reaction has occurred. CH3CH2 CH;CH2 ethanol + Ag NO, C+ H CH, slow H CH a NO: (X= CI, Br or I) CH,CH3 CH;CH, O2NO- ONO2 H;C H H CH3 (R) (S)
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