Professional Documents
Culture Documents
Atdehvde$
ketorn-e
ProPon-z-ol ( OH C C H e) z C H ) + N aBr
'
a\rai1g
Bno NaBr+
Bromobenzene
HzO + ct\rtHctr,
(ProPgn'
Remember, in on organ-tc reaction, nrrcteggyl'1[sw]l\ ract w\th on s,lectrcghi\e . C NO reoetiOh w\lt tako pLacr, ractweoa two nuc\oghitqs or tra,rg etectrophltes)
l- brqrn6gropane --+ HH ll
tl\
aj\)
\-b ro mopropone
' Prirnar/ lrovn6tvo*na
tT J t\
tl
H -e-C- C- Br
H HF\ NHr
H \
HH
t ll lll H
H-C-e-C-NHz
\.T F\ gY,ce's qmoun\ fo pvevent ftsther
H - C- Q- C- Br
, +ast SD{2
' \qast $eric h\ndvtrncl,
'\
subst\tutiorL
2 - br o mo?ropan< . Secondary brsnopropane " l" rno,rzmothy\ gvrfurp+ increaseg+he ster-rc br,t\k
' " hin4otr tt"o- osrtack. by nu-c\aoght\es hence +Vrq rate- \s, s\oweY^
Br
I
cl\ )
.
t- brorn6gropone
nC\!_+hcr\
----->
HsC- C- CH3
I H
HHH
lll
H -C - C - C \tl H HI_\
QlndttlonE
Br
hiI
( C n s l zcH B r+
lt
N o .OH
W (ctqcoto6vis!
Ir \tr/
X ' re+\\
Brr> . so\vent. ethanol
/l 11 v ByP C-Hs \
Nuc\eoghl\t s^bst\tutior(
ie q\kne
Stgp z
H
t
HH
1'
Hydrro\ysTs n\1rile of
l
H-c - oF l I C\\T
H .--.c'
c - cHr ./,.ProP4ne
H -Q_ - C - c - c\l l \l H HH
Q18
"t,
bu\an-l-o\
Lol
> bu.tqnal
q\iver{ eqwc,.lrirn)
Q-t8 te>
Hsc-c - c-oH
lr HH
cHs H tl
CH3cF\2cH2 CHzoH g-
eeuatibn cH3cH,cHrhfiocchemLa\
'r
Stvucture OS grod,rct. H-
i i r ,? a8\ -t-"-t-n
i- iH H|-{
co)
fi\r :1r1
Co\our ggqg&_=
$re4n cns )
C + H r oo
\.\o:\
)<n = mo\ecr,t-\qr formu\q'
F--"\.J}-"\-1 f-2%t*^"G
tol Lol
(4.'t2ttot\6) n = l + 14 n= l + n:\
Mo\gcutar Sorm,,r\q -C\ H 1oO
poss\b\eisomers ot Br,rtqn- l- O
\
O CrrHro ( o\coho\)
H-C-c.
TT
HH ll
A|\ hi
ll
- c- c.- o H
TT
IT
cb)
:)
Bu.ton-z-o\
* -! -i
HH
- c- c-H
oH t-.r
(C)
Bronchedr* o\coho\
H - c '- C - c - - oH
. Z-rvrgthy\gropon- I-o I . f o\cohbl . clo nC* und{-r3o ox-rdctron 2-methylprogan-2-ol
T \"7
?H
H3c-t-cH3
cHa
?H
..\tt,
HgC-c.-CHs
V6l
b) o
Q82 oiii>
Propo'nal +
DNP -__)
the oxidried. cornpouncl does no\ reo.ct wrth FeVrfr{s so\ution cqn not be cr\dehvd,e 9 + con ncit teq qtoo\cohol Henee, tas con^lbuncl. A rnrrst be q 20 o.\coho\ - h{.r,tqn_)_ol
,r t\H bil
teO
&rtan-2-o\
*l
Bu.\anonq
(Comgout&
B)
f i- v _ J t , "
strPa
L { HI o H I lt \ H -Q . - c . - c _ - c - H
HH
lt\
R/ -\
_>
Ho
*o..
Slar z
,"* e./e\ H
t- l
\82
oi)
H\ /.'A
\\
tn"l
'!,
a+ Ht
o
c)
tnoJbr prOdrttct
LI A\ H .+ ( tH - ) hv c \v :6q)i s c x 6qc teog\n* \\e , It w-r\\ on\y qit\o.ck t* covbcvr o* Q-=O o In Q.:C po\au',\y, hence ntr\ "',o o.t\mcte c\ to nr^ctgqglir \ e bcnc\ lros \E s l gqs \T n r bdc 'F ov m teg\
HFI o I I \r H -C - C - - C . - H t\ HBT r HH
^ \ |
dl
J z l N oOH
ct
o
\l
cn\y o\d.-ahyd.e ketorc- w\\\ react G*U / hos *o $wst corrver.tpC \>/ NaOFI . \>vope.vra\ *o Z-hydrroxypro?ena\ using H39@(h\2o , H*) 2-hydreyypropano\ con then no.ct,,ul+tn 7-z 1X aek\
tsr-q- c -c - -H
ll
FIH
$(6C
(}\\)
cHa
YO /'
N0z
H -Br \,-Bn
(fD
Carvone- d.oes 66\ react \I/1th ammoniaeA\ sT\ver irrtn'te CTol\en,s recrgent)
ReosOvt:
cc)ti)Ch\ra\
08+ o) i>
Clrl:co CHr
Reactrin
HcN ->
(cHj.gi,,r*.je=N
conditron:
LHI >
+
HzO Pqplctrbn condRrbn.
oHo
Ciii)
optico,\ cctivlrty + obr\\ to v^otqte the gtone o,F po\arised. lr'ght ? O,i{ferent er\crhtTsngys rotatq'the tbUr+ in ogpos\q o[irection ( one c\oc-KwisQand. one qnt\ ctockuise)
Nqme o'Fpvoduc\=
prqpqn-2-o\
bi)
Ho..
,{.f-*
.cl
18+
bii) bT\il
Tyge cF rn-achonismr nqc\eopvrrtic qad.itTon Feo,.turs oT C--o gruL4P E+ . Btnd. po\o.r\ty . .St o is
8C,._O
+ +
biv)
e.therrq-crnd
H
HCN
\n o. s\ml\qr wc^y ?
H
g\ec-t{cn rrch
3.1
Q-- Ytch
Botln ethgne + CNO q,re e\ectron r\ch spec qs. They w\\\ vepe\ e-o.ch o*ner + c-oh ost rQact in q. nrtc\eoPhili" mohner.