204 Organic Reaction Mechanisms

3.7 Corr elati on tables

for oxida tions
These tables are helpful to know oxidizing agents that can be used
also been given .of
various types oi compounds. The product(s) obtained in each case have

3.7.1 Oxidation of hydro carbo ns

3. 7.1.1 Oxidation of alkan es

Rea2ent1 s~ .--,I
Produc t 3.3.2
Alkane Combu stion / chrom ic acid
c~H,~ CO2+H2O 3.~

--
Qi/Cu
CH3OH 3.5.l
I c~ CH,O 0,.Mo04. 400° C
l
--
. .
3. 7.1.2 Oxidation of alkenes
Product Rea ent Sec.
Alkene Aq.K Mn04 ,
CHJ(CH2)5-COOH Cetyltrimethyl amm. 3.2.1.2
chloride
IGvfn04, H20, NaOH
Cyclooctene Cyclooctane diol + 3.2.1.2
(cis) BzNMe3CI
9,10-Dihydroxystearic acid KMn0 4/NaO H
R ?H
CH3( CH2) r-C-C H(CH 2hCO OH
+ 3.2.l.2
Neutral KMn04

oleic acid 3.5.3

Norbomene cisdiol KMn04, NaOH 3.2.J.2

dialdeh de KMn0 4, neutral)
«--Pinene 1
dicyclohexano 3.2- ·

r ---- -~= :l~l r--- -~P i:n: on~ i~c:ac~id ~r:-..- -1-~K M~~n ~0~4, ~C~6~"6:,=1
18-crown-6
2

Pyridi nium- 3.3.J,4

chlorochromate
(PCC)
BzO Bzo
 Oxidutiol\ 205

CH 3(CH 2) 7C\ CH
10 2

yH 3
(Me) 3CCH 2 C:::::cH Me30-C H 2 - · ?H - CH
3
2
CHO
H3C ~

CH 3
trans olefin
els olefin
trans epoxide
els epoxide

co + C6HsC03H 3.4.1

G.H
{f Minor

or CH3C03H 3.4.1
206 Organic Reaction Mechanisms

3.4.l

t-C4H9OQH 3.5.5
Tl(O-iPr)4

H2C==C==CH 2
/ \c _..-CH2
H2c- \ /
><? 0
3.4.I

R R

0
><? 0
3.4.1

CH2=CH2 CH3CHO 0 2 I PdC}il CuCl2 3.5.l

H OOH
I I I I I I Singlet 02 3.5.2
-c-c= c- -C=C -C-
I I

Singlet 02 3.5.2

OOH

00 cb Singlet 02
3.5.2

~ @--OH · 3.5.2
Singlet 02

oco
. 02 0 .o
Singlet 02
3.5.2
 O·
Xtdntio11 207
/ I I
-,
'c-c
/
-c-o-c -
1,
0 _______ 0I
R-CH HO-C-R1 3.5,)
R,c=C / II + 11
/ 'H 0 O
_.:.;_--r- - - r-:. - - - - - , -___ _
3
3,5.3

H2C Cl 0
Cl 3.5.3
--=--ooiA~c7 - - -<Mc1 -----l

3.5.3

~c, ,'OH Erythro expoxide

C-C-OH
~
t-C4H900H+
'cH VO(acac)2 3.5.5
4 9

cC,H,OH o:·(C,H, { t-CJ!,OOH

' OH + Ti (OC3H1-iso)4
+(+)-Diethyl 3.5.5
tartarate

z:c,H,
O OH
t-C4H90QH
+ Ti (OC3H1-iso)4 3.5.5
+ (-) Diethyl tartarate

t•·C4H900H
OH (+)- Diethyl tartarate 3.5.5
OH

0 Se02 3.5.8

R-cH
R-CH-OH
R-AH I 0s04 /H202 3.5.9
Cyclohexene R-CH-OH
trans-1,2,-dihydroxy (i) h / silver ac~tate 3.5.21
Oleic acid c clohexanol .. nificat1on
Erythro-9, 10-dihydroxy ver acetate 3.5.21
stearic acid (ii) Saponification
Threo-9,10-dihydroxy
stearic acid
208

J. 7· I .,J Ox·1·d 8 t·ion of alkynes

omatic hydrocarbons -t- - - .- -Sec.-

J. 7.1 A Oxidation of ar - --- - - - - ~ -ag
- - Re -en
- ··. -- -··•- - -
- - -
- -- ·····- ·· Product
----on-- -··+-·· - -······ --·-· K.Mn04 or KMn04 I
.
-· ____oc_ab
__'._·dr
-\rom. .ar.k h,
C6H6 I 18-Crown-6 3.2 .1.4
Benzo,c acid Na 2Cr201 I H2S04
Toluene
3.2 .1
M n02I M 020 / Zr 0 2
Benzaldehyde
KMn04, C6H6, 3.2 .1.2
£'I'.\· pinonic ac
id
--
dicyclo-18-Crown-6 I
u-Pmene
-+ -····-··· ---- -- - - -
- - - - - + - - - n04 3.1.1.4I
- - - ··-- KM
o-chlorobenzoic acid
f)-Chloroto/une ; + - - -K.-Mn --
- - - ·+ ·- - - - - ----- 04 3.1.1.4
---i
- -- -- --· -
·••·- , Sy m. Benzen e tricarbox ylic ac id
+ ---- - - - -+-- -
erh yl henzene --- - - - - - - 3.2 .1.4
: 2A.6-Trim - - - + - - - 2,3 KMn04
- - -- . - - ·- -- - - Pyridine -di ca rboxy lic acid
- 1 - - -KM -- - -
Qumolme - - t - - -3. - - - - -ox-yli-c - ac id n04
- -
3.2 .1.4
- --<
Pyridine 4,- dic arb
----- + - - - - -
lsoqumo /ine - - - - - - + - - - 3.3 .4
, -,- - - - - Na2Cr201 I H2S0 4
- - - - - --- --- -- · phthoic acid - - + - - - - - -- - - + - - - - ~

r~=-1
i f!-Na
I 2-m ethylnaphrhalene- . -----4--- - ·· - - - - - - - . H2S04 1 .U .4 -J
--- acid Na 2Cr20 7 , dil
p-Nitrobenzoic
-

co
- -
,1 -- - I
p-Nitroroluene

~1---··
' 0

i
·w--,---:- -- -4 -- C -r O -J/-C
-H_1-COOH

,✓,;
.1 CrO, I CH,COOH I.
).J.4

,
i
·- - - - - ·
-· ·--
I
-t ·--··-·-
. .·-- t- -- ·--- - -- -t -· -
. I I
i· .,.., 14. Ii

---- -
(,~
~
1 /__ ~ o ~ _ _l __
j

I i CrO~ / CH3COOH

________. .. _______ __ __J

 ' .., Oxidation 209

co #
OQ
0

0
Cr01 I CH3COQ_H
3.3.4
I
I.
\··

...... ·--~,,..

ext: /0
Air/ ViOs I 5000
3.5.)

~~
0

H,C◊CH, H,c-0-cHo Cr02Cli

3.3.4

P 'dine

CN
'dine N-oxide
CH1CO3H 3.4.3

N
jJ () N+
C6HsCO1H 3.4.3

I
o-
N 0-
() N
l;t
C6HsCO1H 3.4.3

N
C+)N
I_
0
CH-c o, 02N20s 3.5.1

0 II
CH-C O/
o 400-450°C

H2O2 /Olf 3.5.4

&CH, C?H, ~
3.5.8
SeOi

OCH A 3
OcHO H 3.5.11

OOH OOH K2S20a/Oif

HO 3.5.l l
0 CeH5 OH
I I C6H5

OH o
OH
 ms
◄
21~ Or gan ic Rcuction M1.•du1nis

Al(OCMc .1 )., 1
4uinolinc

- -OC-Me-·)-
-Al(
3 3
+

e. 0
HO . H
H
Pb(OAc 4 I P ridine
H.1 CH _1-CO-CHrCOCH3 HI 04
· ( 'H 1C'HOH<'H.:!CHOHC RC HO +H CH O
.... . RC HO H-C H2 0H HI 04
RC HO +R CH O
RCHOHCHOH R'
3.5.12

H04;··. HO OH
I
I
I
NB S J.5.22

3.5.23

C6 H5COCOC6 H5
+ 3.5.27
KBrO-' ,, OH
(C6HJ2f-C OO H
I
,I OH .
!_

.1. 7.2.J Oddation of 3° alcohols

 Oxid ation 21 .l

J. 7.2.4 Oxi dat ion of diols

--
,---
Diol
~HJ
Product
--- . - -.
• ·••--
,- . __G!'!f~.- r
__Rea ·- .. .. -
~·- .:
0
ct O H c ~ -CH 1
Na:C ri 0 1 , fl 1S04
I

i .l . .l . 1. 1
: OH II 'CH1
0 I
-
CH3 I
··- - - - ·-- -- - . . - -· t

H
+OOH "c=o +o=c '- / :
:
Pt,{O A C)~

-.. - -· +·.-.-~
/
: I

---+ . - --- - -
CH 2 - CH2 -C H2
I
~

HQCH2CH2CH2 CH20H I I ' Ag~< '01 -\:elitl' .l .5 . 14 I

co
CH2 - (CH2) 2 -C H1
0 i'
-·- -. - + ...
(
- -- - - ·+ . ·7I
Ag.: ,("01 ,'.C lilc JS I ➔ ;
HOCHJCH2) 3-C H20H I I · I !

co O
t --··----·- -·
1
I
r --- -··1
,

aO H HOOC(CH2 ) 4 COOH i Ag:<) EtOH-K OH -J 3.5 . 15 I

OH l

3. 7.2.S Oxidation of phe nol s

·--- - - -- - r ··- - - ·· - ___ ·il
--- -,- - -- - · --- - ·gent
.-- --- --- --- -.- --- --= --- -:- -:: ~;- - __ Rea ____ --+- -- Sec.
_-+-----=P:..:r:....::od=uc::.:t_ _ _
1---___;P=-.:h::.=:e:==n=:ol:.____ I U . 1.1 I
I K,C r~O- . f.f,SO"
I
===O=
1

Q -OH
.1 5. 7
HO -@ O _- O ' · PblOAc):
KBr O : 11:SO"
- - ----·--t- -- ·- --. --i
Ii •' -~- --.,7

1- -- -- -- -- -+ -- -- ~-

H,C~OHCH,
0
-- --

H,C VI I CH,
t" ~~ -

I
t -·.
.U . 11

3C__;__o---=-_ _ _
..... --+1
t-H -3_ c_J J_~ --= ---- +-- -H......

J .U I
!

+-_ . _. --t
I
I
•
I !

_____N......:H2~ -4 --- --; :;: --0_ _ _

Meo I OMe
MeO OMe
/ HNO, n1,n x11 1 '

I
.l ,5. 1~
I
.
J_______---·- -·•- ··· -·- -~ -- -- '
j
0 .
 214 Organic Reaction Mechanisms

3.7.3 Oxidation of carbonyl compounds

3.7.3.l Oxidation of aldehydes

Reagent
Product Alk. KMn04
Sec.
Aldl'hyde 3.2}s-
ArCOOI-1 Acidic KMn04
ArCHO 3,ils'
n-Hexanal
R-CH=C H-CHO
R-
n-Hcxanoic acid
cH=CH c-OCH 3
II
0
Mn02 / CN- / CH30H ---
3.2.2

(}-c ooH
02 I Air
Ag20/ 0ir
----
3.5.!
3.s.15
f"J-c HO 0
0 Se02 3.s,g-
CH3CH0
OHC-CHO
COOH --
c50 6 AgO, NaCN 3.5.16

J. 7.3.2 Oxidation of ketones

Product Rea ent Sec.
Ketone
R., 0
C=O II C6HsCOOOH 3.4.2
R/ R-C- OR
0 0
II II 3.4.2
CF3C03H
[>--c -CH3 ~CH -C-O Me

0
o-~-o-OMe o-~-o-Q-oMe 0
RC03H 3.4.2

0 ~
\
'•
0N-o-g ( ) 0N-Q -c- o-Q
2
.

2
RC03H
3.4.2

'. 0
0 0 3.4,2
CF3C03H
 Oxidation 215

r - - - -- -......--- -,
0

I ,H
c,Jt~co_ 3.4.2

____ o__-;-___m_e_Jor_ _ ~inor 0

- - - - -- - - ·-· - 1 - - - - ---1

(rOH 1.4.2

i I

liiPy I OH , NaOH 35.20 I

J5~J I
I
I
➔
J.5.24 ~

En.1ymic oxidn. -' ·"

.-·--·-·ti --·· · ·--·7i

I
:

l:n:1yn11r oxidn. .t o

Me 1 Me L . _ _ _ J_
!

,4..••• • • -- - - - - -- - - -
 ~ I fl Orgamc React i\,n Mcchttnis m-.

3.7.4 Oxidat ion of nitro compou nds

Nitro coml)(lund Product - Reagent -· Sec.

---
~ R- R
'i CH- N0 2 ' c - CHO alk. KMn04 3.2.1.7
R'/ \
I R'/
l I'' or 2'' nitTOCompounds - ·- 7
\
I
!
□NO, [Jo I
alk.KMn 04 3.2. t .7
_ _j
I
l

·- · ~. I

3.7.5 Oxidation of amines

_ _ _ A_m_i_ne_ _ _ -- ..-- -
1 - ~P_ro_d_u_c_t- ---= i-----.!:R~e=aa.ge::.::n:::..:t~--7 \----'S~e..:.c·=---- ~
,' I !
I I' I
-c-N0 2
!
I
alk. KMn04 3.2.1.n
! -C-N H 2
i
! I I
---
~ CH 1<CHkNH2 CH3(CH~)sN02 H202 3.5.4
I
I CttH5-NH.:: C6Hs-N02 H202 3.5.4 ;

{
-~
I

I'
0- ~ NH2 0 0 Mn02 i H' 3.2.2

3. 7.6 Oxidation of cyanid es

r----- Cyanide
'----- --+-- I------Product Rea2ent____- 4
--+-- --~= i.::.:; :_.:._ Sec.
- - _ ~ - -- '.
L_ RCsN I RCONH2 H 202/ alk. 3.5.4
- -· -j
_J
3. 7.7 Dehydrogenation
.,
t-- Startin com und Product Re t Sec. I

Tetralin Na e 3.5.25 I
D --1
~- . ... A(;ena hthalene Acen lene 3.5.25
D _.J
4.8 Cllrrelation tables

Thc!\C tables arc helpful to krnm wh1l'.h n:dunng agents can he used
for reduction of
Jitforcnt functional groups. The produ ch obtained in each case arc also
given. The
,l.'ction numher of thi!-1 hook "here tht:~e reductions have hcen cited are
also included in
thl: tahl\!~ .

,.H.I lltduction of alken~s

. - ---··- -- - - --
Product~ Reagent Sec. ~o.

Alkanc~
5'!to Pd-C: Pt o~.
-\lkl·11, -L!. I
Raney Ni

\ 1ono,uh~t ituh.:J j(C,11,hPJ: RuCIH

AlkanL.'~
.tlkl•fl~'- IIH ·11 <. H ·'
25 2 Organic Reaction Mechanisms

C6H5CH 2CH2CH2OH Raney Ni /l-h 4.2.I

C6H5CH=CHCH2OH
CXCHi
CH3
Major
CXCH3 CXCHi
+ Pt02/lh 4.2.1

CH3
'CH3
Minor

O=y
070 CH{
I
Major Pt02/H2 4.2.1
: +
CH3

070 H .
CH{
Minor

4.2.1
. Nc-O-cHz{:H3 Pd/H2

4.2.1
Pd/H2

.......------------· ---
 Rt:d•.u.11,m 2 ~ 3

OH

CJfsCH=CHN02

Hi/[(C6Hs)3PJ3 RhCI 4.2[BJ

(C6H6-C2HsOH)

0
H2/[(C6Hs)3P)3 RhCI ~.2[B]
C6H;( 1-I=CHC00CH2C6Hs C6HsCH2CH2COOCH2C6H5 (C6H6)

H2/[(C6Hs)3PJ3 RhCl 4.2[B]

CH2=CHCH2-S-C6Hs CHJCH2CH2SC6Hs (C6H6)

-CH2-CH- B2H6 4.3.7

-CH=CH- I
OH

H3 CH3 Na/Li-NH3 4.4.2

I
CH=CH2 CH3-C=CH-CH3

"c-c/ Diimide 4.5.2

/I I"-.
H H

Diimide 4.5.2
CHJ(CH2)9C00H
 LS4 Organic Reaction Mcdu:ni...ms

Diimide 4.5.2

CO OH Diimide 4.5.2

CO OH CO OH
0

Diimide 4.5.2

CH3 H3C

I Et3SiH/CF3COOH 4.5.4

Ph2SiH2 4.5.4
ZnCh-Pd(PPh3)3

ofalkynes

Reagent Sec. No,

Products
~ -- -- -- -- -- -- --5%-- ~- -- --- -
Pd-C; or 5o/• N• 4.2.2
~Jkenes BaSO.
Alkanos Pt02 or Raney Ni
--·
4.2.2
 LindM'" cata.lyst IH 2
4,2.2

C2 llh , /(C l l2hC01fl

I C= ( .', Haney Ni / Hi /
11 It
C2 H~OH 4.2.2
(cis)

C2H5, /I
· C= C
. H.,. '(C H2 hC 02 H Na / NH 3
4.4.2
~ - - - - - - - -- -__(tra
ns)_ __ _ _ _ _ _ _ __ _

U J Reduction of aromatic hydroc

arbo ns

Products Reagent Sec. No.

0 0
Raney Ni/H 2 4.1.3

Major Raney Ni/H2

+ 90'\ 27 S atm.
Oil

W~
l
. Minor
 25 :, Orpni•: Reaction Mech:misms

~
COOH
aC H O H C 02 H aC H O H Rh-Alz03/H2 4.2,3
I
~

aC H 2C O O J- i
Pd-CII-I2
~
I 4.2.3

cis-Decalin Pt/ H2 4.2.3

Naphthalene

trans-Decalin Ni / H2 4.2.3

CD Na /C2 Hs OH
(75-80°) 4.4.I

OH
OCJ OH
Na-isoamyl alcohol
130-140° 4.4.I

Na-C2HsOH 4.4.I

Li/NH3 4.4.2

Na!C2HsOH 4.4,l

Aromatic carboxylic Hydroaromatic Pt02 or Ra ney Ni/H2 4.2.3

acids _ carbocylic acid or 5% Rh(Ah03)

R R R

: I
- - - - - - - --
oor() Na/liq. NH3

-- -- - ~ -- - - - - - ---- - -
4.4.2
 l i

oco Nu/umyJ ;,Jcoh<,f 4A ,2

Nill (z (250-270' )
1
4.2,3

4.8.4 Reduction of carbonyl compounds

(a) Reduction of aldehydes

Products Reagent Sec. No.

Aldeltydes
Na- C2H sOH 4.4. 1
R-CHO R-C H20 H

..
. . Alcohols
2-4% Pt0 2/ H2
5% Pd/C Raney Ni
4.2.4

LAH 4.3. 1
CH3(CH2)4CH20H
LAH 4.3. 1
CH3CH::::CH CH2 0H
LAH 4.3. 1
C6HsCH2CH2CH20H
NaB Ri 4.3.2
OH)4CHO CH2 0H(C HOH )4CH 20H
Na8 H4 4.3.2
NCCH2CH2CH20H
NaB HJC N 4.3.3
NNHSO.zC.,H.·P·CH, CH3(CH2)2CHJ (DM F, 100°)
of aldehyde•
258 Organic Reaction Mechanisms ·

n~H1rCHO n-CgH19CH20H HCOiH I EtMgBr

-----
4.5.3

Ph~CH O Ph~OH (Et20)SiHMe 4.5.4

CH3CH=CHCHO CHJCH=CHCH20H Enzymic redn. 4.7

(b) Reduction of ketones

Ketones Products Reagent Se.c. No.
2-4% Pt02/'H2
Aliphatic ketone Alcohols
5% Pd/C/H2 Raney 4.2.4
R-CO-R' RCHOHR'
Ni I H2
CH3CH2COCH3 CH3CH2CH(OH)CH3 LAH 4.3.1
B2H6 4.3.4
CH3COCH2COOCH3 CH3CHOHCH2CH20H LAH 4.3.1
NaBRi 4.3.2

LJO H

IT°H LAH 4.3.l ·

cro o:H LAH 4.3.1

CH3COCH2CH2COCH3 CH3CHOHCH2CH2CHOHCH3 LAH 4.3.1

Cycloheptanone Cycloheptanol Na / iso-PrOH 4.4.1
OH
I
(CeH&}.zCO CsHsCHCaHs
+ Na/ ether 4.4.i
(CaHsny-rCaHs)2
OH OH
.CH3, (CH3)2C-OH Mg-Hg 4.4.3
C==O I
· CH{ (CH3)iC-OH Photoreduction 4.6
R .
R,
'c==0 /CH2 NH2-NH2, KOH 4.5.l
' R.'/ R'
 Reduction
259

.--· __
() .
..._.
OH --
PhAy Ph)y Br
(Et0)1SiHM e 4.5.4

Br

(CfiHsny- y(CJ-ls)i .
lntCH 1COOII 4.5.7
('
11
tf 5COC11l~< OH OH

R II
-c-R' RCH(OH)R Zn/NaOH 4.5 .8
0
0 HOH
~C02Et Baker's yeast 4.7
~C02 Et

(.\·)-Alcohol

0 HO

~ ~ /

' T. brockii 4.7

4.8.5 Reduction of nitro and nitroso compounds

- - ·- - -
- - - - -·-·-- -
Substrate
- - - - .. - ______
..

,_,
Products
. -·· --- ·-
Reagent
-· ·- - - - - ---····
Sec. ,o.
... ""
PtO:/H2 5%
Nitro compounds Amine 4.2.5
Pd-CIH 2• Raney Ni
\
C"H~CH=CHN02 Pd-CIH2, Alcohol 4.2.5

RCH.?C'H( N02 )C Hi 4.3.1

CHO CHO

Q I
~ SnCI: IICI 4.5.5

NO,
: :,. . I NH,

Sn + f I( ·1 4..5 .6

Mg Alcohol 4.5.11
0 ·- • -•-•- -
. M- - -- • ,0
2(,fJ
Orl(.an k R~al."lio n \.1cl."han,smi.

- - - - -- -- - - - ---·- -~
NaSH -~-----
4.5.12

Nitroso compound~

cr
N- C'I- H~
.
I 4.5 .5
NO
~

s
du cti on of nlt rfl es, azi dc s, oximes. ha lid es an d cpoxide
4.8.6 Re
- --- -- --
Reagent Sec. No.
Substrate Products

Pt0 2/H 2I Alcohol 4.2.5

Nitrfles Amines

5% Pd-C 4.2.5
Amines
RC =N Raney Ni 4.2.5
Amines
LAH 4.3 .l
R-CHO 4.3.4
B2Ho
4.4 .1
n-C6H13NH2 Na-C2HsOH
n-C,H 11 CN
4.5.5
C6HsCHO SnCb/HCI
CJ{sCN
5% Pd-C; Pt02; 4.2.5
Amines Raney Ni
Azides
4.11
RNH2 LAH
RN,
4.2.5
Amine 5% Pd-C. Pt02
Oslme 4.3.3
Na8H3CN
4.3.1
(C,,HshCHNH2 LAH
(C,,HdzC.,NOH 4.4.1

-- •- ·• .. --- ..
n-C,H,~NH2 Na-C2H~OH ---
 Hydrocarbon S% Pd-C, Raney N' ~

or 501 p
, o d-BaSO,.
I
flaUdes 4.2[A)
R(CH2)nCH3 LAH
R(CHl)nCH2Br 4.3. l
CH3(CH2)sCHJ NaBH 3CN
C1-h(Clh)HCH2I 4.3.3

[paddes
-cH-C H2Br CH3-CH- CH-C H3 NaBH3CN 4.3.3
Cl13-CH / \ /
'o o LAH
-cH-C HJ RCH2CH(OH)CH3 4.3. I
R-C~ I
0 RCH2CH(OH)CH3 NaBH. 4.3.2

RCH2CH(OH)CH3 B2H6 4.3.4

4.8.7 Miscellaneous reductions

Products Reagent Sec. No.
Substrate
[(CJfs)3PJ3 RhCl 4.2[8]
CJlsCH=CHCHO CJ!sCH=CH2 (CJf6)

RCOCl RCH20H LAH 4.3.1

NaBH.. 4.3.2
[(CJfs)3PJ3RhCI 4.2[B]
CJisCOCl CJ!sCI (CJ!6)
R(CH2)uCOOH R(CH2)nCH20H LAH 4.3.1

CH3CH=CH-COOH CH3CH=CH-CH20H LAH 4.3.l

CH3CH2COOH CH3CH2CH20H LAH 4.3.l
CH3Cff=CH-COOEt CH3CH=CHCH20H. LAH 4.3.1

Nc-Q --coc 1 -Orno LiAIH(t-OC4H9)3 4.3.1

~l{(CH2)aCON(CH3h CH2=CH(CH2)sCHO LiAIH(OC2Hs)3 4.3.l

262 Organic Reaction Mechanisms

0
II RCH20H + R10H Na/ C2HsOH 4.4.I
R-C -OR 1
(CH2=CHCH2)2S (Cl-l)CH2CH2)2S Diimide 4.S.2

C6HsN=NC6Hs C6HsNHNHC6Hs Diimide 4.5.2

©:CONHC H (XCHO 6 5
PCls, SnCh 4.S.S
CH3 CI-13
0

Sn+ HCI 4.5.6

0 H H
OH

0
NaHS03 4.5.9
[C6HsN=N]+c1-

4.8.8 Hydrogenolysis ·
Products Reagent Sec. No.
Substrate

0) ,Q
RaneyNi/H2
Alcohol
4.2.6

CHJO~ 'CI (X.o O

. R Zn/HCl 4.2.6