Advices For Studying Organic Chemistry

11.21 SUMMARY OF REACTIONS OF ALKENES, ALCOHOLS,

AND ETHERS

CH 3 CH 2 OH

CH 2 C(CH 3 ) 2 /H 2 SO 4

Na or NaH

TsCl

MsCl

HX

PBr 3

SOCl 2

TBDMSCl

HX (X = Br, I) X

RCOOH

O

O

ROH, H+

ROH, H−

Na RCH^2 X CH 2 R HX (X=Br,I) XX

Ts Nu

− (^) (Nu− (^) = OH−, I−, CN−, etc.)
Nu
Ms
X
Br
Cl
RONa OR
CCH 3
CH 3
CH 3
H 3 O+/H 2 O H HOCCH
TBDMS
ROCH OH
ROCH OH
Nu−^ (Nu−^ = OH−, I−, CN−, etc.) Nu
Bu 4 N+F−, THF H FTBDMS
H 2 SO 4 ,140oC
(Section 11 .15A)
H 2 SO 4 ,180oC
(Section 7.7)
(Se and ction 6.111.9)6B
(Section 11.10)
(Section 11.10)
(Section 11.13)
(Section 11.14)
(Section 11.14)
(Section 11.15C)
(Section 11 .15D)
CH 3 CH 2 OCH 2 CH (^3) (Section 11.16) 2 CH 3 CH 2
H 2 CCH (^2) (Section 11.17)H 2 CCH 2 (Section^11 .18)
(Section 11.18)
CH 3 CH 2 O (Section 11 .15B )CH 3 CH 2 O (Section 11.18) CH+ RCH 3 CH 2
2
CH 3 CH 2 O (Section 11.11) CH 3 CH 2
CH 3 CH 2 O
CH 3 CH 2
CH 3 CH 2
CH 3 CH 2
(Section 11.15B) CH^3 CH^2
CH 3 CH 2 O (Section 11 .15C) CH 3 CH 2 O + 3
CH 3
CH 3
CH 3 CH 2 O (Section 11.15D)
2 CH 2
2 CH 2
(Section 11 .11) CH^3 CH^2
CH 3 CH 2 O +
Figure 11.6 Summary of importrant reactions of alcohols and ethers starting with
ethanol.