Advices For Studying Organic Chemistry

(Wang) #1
2) group or of one of the anhydride linkages of an

3) , these phosphates exist as negatively charged ions and hence are


  1. E s in which the energy


esters are especially important).
Although hydrolysis of the ester
alkyl triphosphate is exothermic, these reactions occur very slowly in aqueous
solutions.
Near pH 7
much less susceptible to nucleophilic attack ⇒ Alkyl triphosphates are relatively
stable compounds in the aqueous medium of a living cell.
nzymes are able to catalyze reactions of these triphosphate
made available when their anhydride linkages break helps the cell make other
chemical bonds.

H 2 O

Ester linkage

Anhydride
linkage

P slow

O
RO O
OH

P

O

OH

OP

O

OH

OH

ROH

P

O
RO O
OH

P

O

OH

OH

P

O
RO OH
OH

P

O
HO O
OH

P

O

OH

OP

O

OH

+ OH

HO P

O

OH

OP

O

OH

+ OH

HO P

O

OH

+ OH

1.12 CONVERSION OF ALCOHOLS INTO ALKYL HALIDES



  1. Alcohols react with a variety of reagents to yield alkyl halides.


1


1) Hydrogen halides (HCl, HBr, or HI):

C

CH 3
OH
CH 3

H 3 C + HCl (concd)

oC
94% C + H^2 O

CH 3
Cl
CH 3

H 3 C
25

CH 3 CH 2 CH 2 CH 2 OH+HBr(concd) reflux CH 3 CH 2 CH 2 CH 2 Br
(95%)
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