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Exercrle -

Atdehvde$

ketorn-e

Ql+ bt) Ssuqlqrs_


. trlrrcteophi\ic substitqtTon (CHs)zCH(Bv.) + . ba.nze.ne s- .ich 4 q\tract eledroghi12o.'\Y, wl\\ not nr,,r.c\eophil cl I E\im\no$ron CCH3)z CH Ctsr) + NaoH -> NGOH

(!-lt[ ar) 2-Bromopropane


' 8+ C cltrac*s nrrctoogt,rte

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\

\- o.mrn6pro?one Cre proprTtamin)

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\

----->

lcru.\anor-c crcia. has Tnene&secl._uy CHz qn\t a


I

HsC- C- CH3
I H

+Ve. ea,rbon e.\a-rn

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

Hs@ ( ie Hzo , H@.


di\ule o.cio\
,l

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

o 2-mnthy\progon- \-o\ ' , lo o\cohol eo.n ue. $unther oridisec(

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&_=

Fngir icq\ frvmu\a

C= H = O 6q.9 r3.s - er.6, 16 E= r-SA- - r 3.S: tgS

oranSC to c c-n>o12- ->

$re4n cns )

C + H r oo

\.\o:\
)<n = mo\ecr,t-\qr formu\q'

(Erngr-"iea\ fovmu\q) q\\l

F--"\.J}-"\-1 f-2%t*^"G

bu\an- \-o\ b,^tqn-2-o\

tol Lol

, br.r.tona c o\d.n hytu I > h^rtanone c ketonq)

(4.'t2ttot\6) n = l + 14 n= l + n:\
Mo\gcutar Sorm,,r\q -C\ H 1oO

To distingdrstao\d.ohyd,e Srom ketone


:) use S-ilver mirror test r qd.d-tollen's reqignt to +ha sumg\e- ond* wavryl \t rn o- wcrter bath . A sT\vermirror is fuftneA in titeq\dsl^yd.c_somptq , b(^t not Sr ketone A\ternoJiver Fehting's so\r,,-tior.r b\,r.e -+ recldishbror. (Q,^.1.t* -+ Qrr'+)

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)

heatec\ undqr re*tua

:)

tnd,rlctes $unther oKd.qtion I l ^_[_[_[_".f .r .


HHH

Bu.ton-z-o\

* -! -i
HH

Prod,qct. bu\aroic. oi,d \oH


2-methV\gropon-\-o\

- 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

3- isorner wi\\ get oxiaised by ox\drii13 ogent


+ c-an not b.e 3o o.l cohol C 2-methy\propon-2-ol )

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
\\

b\ir . pHtoo high 9


lgrogenal)

tn"l

henc . s l ep 2 pH tog tow g

'!,

Vry \oW ooncQnt"qtin

a+ Ht

L_qc or nesv e( y s\o$l CNL

H ' - C:C ' \ c-r-r

o
c)

p)vctonqtac\, therafij-rq / tCN-] concOntrcr-tioyris \ow + Stepl l^ecOr-.os v g v v s \ow

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

o.ii) Brze "rff.f*i|,.


c.Hr

YO /'
N0z
H -Br \,-Bn

(fD

Carvone- d.oes 66\ react \I/1th ammoniaeA\ sT\ver irrtn'te CTol\en,s recrgent)

degcnd.s how much Bn> Yo\ tlst , mcY gef

Cjnlovinq\ron usin3 PC\s et roorrrternprrqtur

ReosOvt:

crbsev<-o oQ o\dohyda- 8Y1Jt/tP

cc)ti)Ch\ra\

c rno\ec,r.r.\e virt{n on qsymma-tvfc e-ovbu't

08+ o) i>

Clrl:co CHr
Reactrin

An osywrnnetrtrc carbgr't L o earbtm otJrm whiclr R, tot\ae4 to l+ d.iQeYent ctcrans / grougs

HcN ->

(cHj.gi,,r*.je=N

conditron:

hqt qnd.or re+\\^x gtVrqno\c solvent 2-hydrox/_2_methy\propanitvile

Nqrng oF prod,rrct r \i) c-H3OOCH3


osYnnmqtvr-c ccrrlotm ( h,o^dqd-+o f+ a\+ngYq^+ grlugs)

LHI >

CHsCH CoH) CHs

+
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

+ +

eqttrve How t\n\s.-Seqture orries ?

morQ e\ectrone3o+ive it'\on Q Corbon qttro.gts nuc\eophile

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.

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