H 3 C-CH 2 -CH 2 -CH 2 -OH +(NH 4 Br, NH 4 Cl,H 2 SO 4 ) --> H 3 C-CH 2 -CH 2 -C

Question

H3C-CH2-CH2-CH2-OH +(NH4Br, NH4Cl,H2SO4) -->       H3C-CH2-CH2-CH2-Cl or

    Or H3C-CH2-CH2-CH2-Br

C4H10O + (NH4Br,NH4Cl,H2SO4) -->    C4H9Clor C4H9Br

Explanation / Answer

CH3CH2CH2CH2-OH + H2SO4 ===> CH3CH2CH2CH2-OH2(+) Cl(-) + Br(-) ===> CH3CH2CH2CH2-Cl + CH3CH2CH2CH2-Br + H2O Cl- and Br- displace H2O. (CH3)3C-OH + H2SO4 ===> (CH3)C-OH ===> (CH3)C-OH2(+) ===>(CH3)3C(+) ===> (CH3)2C=CH2 (CH3)3C(+) + Cl- + Br- ===> (CH3)3C-Cl + (CH3)3C-Br n-Butanol reacts by an SN2 mechanism via a protonated transitionstate. t-Butanol forms an intermediate carbonium ion in an SN1mechanism. Depending on the specific carbonium ion, a certainamount eliminates to isobutylene no matter what. The nucleophilesreact with the surviving carbonium ion.

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