1) 1-chloroadamantane is a tertiary halide, yet it is 10,000 times slower than t
ID: 964242 • Letter: 1
Question
1) 1-chloroadamantane is a tertiary halide, yet it is 10,000 times slower than tert-butyl chloride when allowed to react with silver nitrate in ethanol. EXPLAIN WHY2) Are alkyl fluorides good substrates in SN2 and SN1 reactions? EXPLAIN 1) 1-chloroadamantane is a tertiary halide, yet it is 10,000 times slower than tert-butyl chloride when allowed to react with silver nitrate in ethanol. EXPLAIN WHY
2) Are alkyl fluorides good substrates in SN2 and SN1 reactions? EXPLAIN
2) Are alkyl fluorides good substrates in SN2 and SN1 reactions? EXPLAIN
Explanation / Answer
1)
in one word this answer is Bredts rule
let see in detail
first of all these will react with silvernitrate and form he carbo cation
i hope reaction is clear to you
i fyoy look at the 1-chloroadamantane though it is tertiery alkyl halide it cannot form the tertiery carbocation this is
because tertiery carbo cation should have planar structure (because of SP2 hybridisation) but it can not attain planar structure because of the bridged head positin because all the alkyl groups have to move to 120º bond angle it is not possible with that bridget system
this is called bredts rule
if you want even more about bredts rule type in google and read
where as siple tertiery alkyl halide can form more stable carbo cation easily so it can react quickly
2)
no for both it is not a good substrate
because C-F bond is very strong it cannot cleave so easily either in the SN1 and SN2 reaction because of the difference in electronegitivity between the Carbon and Fluoride is more bon bond length is very shory so bond is very strong
Related Questions
Navigate
Integrity-first tutoring: explanations and feedback only — we do not complete graded work. Learn more.