Download Lecture Handout on Alcohols and Phenols - Organic Chemistry | CHEM 238 and more Study notes Organic Chemistry in PDF only on Docsity! 17-1
Alcokels £ Phendls
ou
\
Co. Dit ok
a<\ CaN yak
otcoke)
oi ae pews) enc | a
{ AAD
* yes +
GL” alcohol Challe
wiadered
sho bases aS al ho-prles
but doit do Syd rea chons LS
Aci dicey
Oo
ROH « ibe += RO + tO
Poa
1 alhoede
selvent phimeade
e . Sel el
TRow |
pKa == log Ka.
- Teoh)
pKa = pl + loge”
gh = pKa neg TRH}
Te]
heidi ty Sele 2
Hy O pKa = is. 74 not an acuck
Ege
CHa coy 6 ( week. acocks
HE 3.48
O- NOn —1.3 | pero
tcl md “$
Cent. bese stabeTihy
most alleshols About (The water
CH Cibo # 16.0
cHoH 1S. .o4
nt cy
-¢ 3.00 cont. bae lecs ears
gon 5 By
a"
solvated
q CFs C—O (24
CF,
“con 9-6
cK p- suf 26
-~OCH3 -Ch -NOn Jy
K i
cor 9.89 10-2} 938 715 060 |
_ net
fable 24.2 (oy > 4.63 5.34 398 1.00
CHy He 0.66
19-5
Grignard Reagents pr Alcohol Sym theses
e-x MP ReMgX acts like R2
work for sp?, sp® halides err Mg MgBr
werks
© y RMo X ether on
eS
Lo be alleyl, H, aryl
BUT cannot contain -OH, -NH, -SH or — COOH
gioups © «2 oO
OH + RMgX -_- oO: Ma X + RH
4
° 7 M4 alkane
R-MgX O
WW os 7 f
R-CN og REN eu + HOR
K After aadifica hon
Reactions of Alcohels
ott
== HO 7
1) — alkenes me x pie
Rives mere shbShtuted isomer
CF or [» ov]
E1 mechanism fer T° ££? alcohols
low temp. alternatrve Pocls [pyridine
ct
Q~ pret
ce 4
a u u H
3
ol
{J-
Alcohol reactons contd. v6
2) — >» halide
me -X, ost , eh KX
Ww? mere diffrcult ; but Jn2 ur th PBrs
x? SOC, -Cel or PBs > —Br Sn
3) tosylates, mesy lates lakternahves to -X)
reagent MeLO)-so,ct ar CHa SOZCL
o
stample use: o
PBr. Bro CHCl” ee
oo eee CO Se CY
2 \ MeSO,ct ote ‘ oO “ye
vn
=n
Pt" z Sve
4) Oxidaton
tol we
CH36H CH,O ——» HCL > CO
RcH,eH ——» RCH > R-c2°
H Nou
ROW '
HO” Ry a0
R R
we
AL alcohol 5 no veacthon
oxidants : # © Crd3
LON cro,ct or KMady
pee Mas Cig07
aad
= Hylr0y
chromic
Acid
17-7
Alcohol Oxrdaten Meck.
By or cS
A q
C—~OH ——> Dot ac —> “c=
“7 “7 u /
need -OH and ~H on same C atom
In the case of primar alcohols
RCH pce eo .
ZH chee REZ, reaction step
|kocroy [20
~? 20 a on
RO = R-C—oH _ RoCa,
ra
eed —OH peers. to avoicl inter ference
Heyer es NBT stead ot
a7 is aciel
se NoT OBTHINED
oh IC
(CHs),SicL
Et3N See pp 662-684
Me TMS
Me- Si- Soy Mg” Nose
\ — —> —_»
Me
cl ct
\ Me
RNo + sit —_* Roser me
af ) “Me 1 ‘Me.
Me. Me-
