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SOLVINGPROBLEMSBASEDONORGANI

CCONVERSI
ONSI
NSUBTLESTWAYSAND
SHORTESTPOSSI BLETIME
Present
edBy:
-
Lokeshsur
ediaPGT(Chemist
ry)
KVSACVast r
apur(Ahemdabad)

I ON:St
NTRODUCTI udent
smemor
iseal
lor
gani
creact
ionsbutunabl
etor
ear
range
al
lthesereacti
onsandsolveprobl
emsbasedonorganicconv
ersions.Thi
sisan
eff
orttosystemati
zeandrearr
angetheor
gani
creacti
onstosolveproblems
basedonor gani
cconver
sions.
METHOD:
- Organi
cconv er
sionsar
ecl
assi
fi
edas:
-
A. Ali
phat
icconver
sions.
B. Aromati
cconversi
ons

(
A) ALI
PHATI
CCONVERSI
ONS: Al
i
phat
icconv
ersi
onsf
urt
hercl
assi
fi
edas
St
ep-
upconv
ersi
ons
(
i)ByWur
tzr
eact
ion:

(
ii
)Thr
oughcy
ani
de:

(
ii
i)Thr
oughGr
ignar
dreagent
:

(
iv)Thr
oughAl
kyne:

(
b)St
ep-
downconv
ersi
ons
(
i)Thr
oughcar
boxy
li
caci
d:

(
ii
)ByHof
mannbr
omami
der
eact
ion:

KEYFORCONVERSI ONS
(ByLokeshSur
edi
a)

Sl Reagent Gr
oupOut Gr
oupI
n Remar
k
No
0
1 KMnO4/H+ -
CH2OH -
COOH Str
ongOxidat
ion(2 alc
ket
one)
2 Li
AlH4 -
COOH -
CH2OH Str
ongReducti
on(ketone
0
 2 al
c)
3 Cu/573K orCrO3 -
CH2OH -
CHO Dehydr
ogenat
ion
4 PCl
5 or SOCl
2 -
OH -
Cl
5 Cl
2/Δ or Cl2/UV -
H -
Cl Fr
eeradi
calsubst
it
uti
on
6 AqNaOH/KOH -
X -
OH Nucl
eophi
li
csubsti
tut
ion
7 KCN -
X -
CN St
epUp
8 AgCN -
X -
NC
9 Al
cohol
i
cKOH -
HX = Dehy drohalogenation
(Stzf)
10 Mg/dr yether Mg R-X R- MgX
11 HBr >=< H,Br Mer kovnikov
12 H2/Pd- BaSO4 -COCl -
CHO RosenmundReduct i
on
13 Zn-Hg/HCl >C=O -
CH2- Clemmensi onReduct ion
14 NH3/Δ -COOH -
CONH2 -
COOH+NH3 - COONH4
15 Br2/NaOH orNaOBr -CONH2 -
NH2 StepDown(Hof fmann)
16 HNO2 orNaNO2/ HCl -NH2 -
OH HONO
17 CHCl3/ alcKOH -NH2 -
NC Car byl
ami ne
18 P2O5 -CONH2 -
CN Dehy drati
on
19 H3O+ -CN -
COOH Hy drol
ysis
20 OH- -CN -
CONH2
21 Li
AlH4 -CN -
CH2NH2 Reduct
ion
22 RedP/Cl 2 α-Hofaci
d -
Cl HVZReaction
I
nbenzener i
ng
23 Fe/X2/ dark -
H -
X Halogi
nation
24 CH3Cl/Al Cl3(
anhy d) -
H -
CH3 Fri
edelCraftal
kylat
ion
25 CH3COCl /AlCl3(
anhyd) -
H -
COCH3 Fri
edelCraftacyl
ati
on
26 Conc.HNO3/ con.H2SO4 -
H -
NO2 Nit
rati
on
27 ConcH2SO4 -
H -
SO3H Sul
phonat i
on
28 KMnO4/H+ -
R -
COOH Oxidat
ion
29 CrO2Cl2/ H+ -
CH3 -
CHO Mil
doxi dati
on(Et
ard
Reacti
on)
30 Sn/HCl orFe/ HCl -
NO2 -
NH2 Reducti
on
31 NaOH/623K/300at m -
Cl -
OH
32 Zndust/Δ -
OH -
H
N2+Cl
-
33 NaNO2/di
lHCl/273-278 -
NH2 - Di
azor
eact
ion
K
N2+Cl
-
34 CuCl/HCl orCu/HCl - -
Cl Sandmeyeror
Gatt
ermann
N2+Cl
-
35 CuBr/HBrorCu/
HBr - -
Br Sandmeyeror
Gatt
ermann
N2+Cl
-
36 CuCN/KCN - -
CN Sandmeyer
N2+Cl
-
37 KI - -
I
+ -
38 HBF4/Δ -
N2 Cl -
F
N2+Cl
-
39 H3PO2 orCH3CH2OH - -
H
+ -
40 H2O /283K -
N2 Cl -
OH
N2+Cl
-
41 HBF4/NaNO2,
Cu/Δ - -
NO2
N2+Cl
-
42 C6H5-
OH - -
N=N-C6H5-
OH Coupl
i
ng(p-
hydr
oxy)
+ -
43 C6H5-
NH2 -
N2 Cl -
N=N-C6H5-
NH2 Coupl
i
ng(p-
amino)

React
ionsofGr
ignar
dReagent
Gr
ignar
dreagent+ Anyonebel
ow+H2O  Product
H2OorROHorRNH2 R-H
H-CHO R-CH2-
OH ( 10al
c)
R-CHO R-CH(OH)-R(20al
c)
R-CO-
R R2C(OH)-
R( 30al
c)
R-
MgX
CO2 R-COOH
R-CN R-CO-R
HCOOR Aldehyde
RCOOR Ketone

NB: i
)Dur i
ngr eacti
ongener all
ychangestakeplacei
nthef uncti
onalgr
ouponlysoseet he
functi
onal
groupv er
ycar eful
ly.
i
i
)Rememberst r
ucturalf
ormulaofallt
hecommonor ganiccompounds(wi t
htheirI
UPAC
andcommon
names)
ii
i
)Wur tzReact i
onandAl dolCondensat
ionarenotincl
udedi nthet
abl
ealthoughtheyare
veryimpor t
antf orconversi
onssost udythem .
iv
)Byt akingexampl espracti
ceall
theabovecases(f r
om 1t o43andGrignard)
v)Practi
ceonl yf r
om NCERTbook.
vi
)Startpr acti
cingNOW !

Howt
ouset
het
abl
e?Seebel
ow.

Exampl
e:Seeno7i
nthet
abl
e

Di
rect
ional
Proper
ti
esofgr
oupsi
nbenzener
ingf
orel
ect
rophi
l
icsubst
it
uti
on

Or
tho-
par
adi
rect
inggr
oup:
-R,-
OH,-
NH2,-
X,-
OR,-
NHR,-
NR2,
-NHCOCH3,-
CH2Cl
,-
SH,-Ph

Met
a-di
rect
inggr
oup: -
NO2,
-CHO,-
COOH,COOR,-
CN,-
SO3H,-
COCH3,-
CCl
3,NH3+,
-

(
C) Conv
ersi
onsofsameno.ofcar
bonat
oms
(
B)Ar
omat
icConv
ersi
ons
CONCLUSI ON: -
Nowst udent sar eabletosol vet hepr obl emsbasedonor ganicconv ersi
onsbyusi ngthis
met hodi nshor t
estpossi blet i
me.Theycanal sosolv et hepr oblemsofwhathappenswhen?
Compl etether eacti
onset c,whi chcov ert hemaj oraspectofor gani cchemi stry.These
conv ersionchar tsmakeor ganicchemi stryinteresti
ngf ort hest udent s.Teachercanal sousei t
asat eachingai d.
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--ASSI GNMENTFORCLASS–XI ISc
(CHEMI STRY)ORGANI CCONVERSI ON- --
( 2t o3mar ks)
CONVERTTHEFOLLOWI NG: -
Q.I#Ani li
ne t o (a)benzoi caci d (b)benzoni tri
le (
c)iodobenzene
(d)phenol (e)acet ani l
ide (f)p-nitroanili
ne ( g)sulphani l
icacid
Q.II
#Benzoni tr
il
et o ( a)actophenone ( b)benzoi caci d ( c)benzami de ( d)1-pheny l
met hanami ne (e)ani l
ine
Q.II
I#Phenolt o ( a)sal i
cy l
icaci d ( b)sal i
cylaldehy de ( c)t oluene ( d)acetophenone
(e)aspi r
in
Q.IV#Acet yleneto ( a)Lact icaci d (b)Acet al
dehy de (c)Acet icaci d
Q.V#Benzal dehydet o( a)α- hydroxypheny lacet i
cacid ( b)Benzophenone( c)3-pheny l
propan-
1-ol
(d)Benzy lalcohol
Q.VI#Hept -1-eneto ( a)Hept anal ( b)Hexanal ( c)Hexanoi caci d (d)Hept anoic
acid.
Q. VII#Acet aldehydeto( a)but an-2-one ( b)but -
1,3-diol ( c)but -2-enal ( d)butan-1-ol ( e)
butanoi cacid ( f)but-2-enoicaci d ( g)Lact i
caci d ( h)nitropropene- 1
Q.VIII#Benzenet o ( a)m- ni
trobenzoi caci d (
b)pheny lacet i
caci d (
c)p-nitr
o
benzal dehyde (d)p- nitr
obenzoi caci d (e)met hy lbenzoat e (f)met a-
nit
roacet ophenone
Q. I
X# ( a)Benzoi cacidf rom chl orobenzene ( b) t -but y
lalcoholf rom acet one (c)et hanol
topr opan-2-ol
(
d)Met hylcyanidet opr opanone- 2 (e)Acet ophenonet o2-
pheny l-2-but anol
(f )Met hanalt opr opan- 1-ol (g)br omobenzenet o1- pheny lethanol ( h)Pr opanal
toBut anone
Q.X# ( 1)Et hy lami nef rom acet aldehy de (
2)Et hanoy lchlor idet omet hyl
nitr
ile
(3)2- ni tr
opr opanet oacet one (
4)Hexanami det ohexani tril
e
(5)Pr openet oacet oneandv i
cev er sa (6)Tol uenet obenzal dehy de
(7)Et hy lbromi det oet hy lami ne (8)Ani solet op-met hoxyacet ophenone
(9)Benzoy lchl ori
det obenzoni trile (10)n- propy lalcohol t
ohexane.
(11)Hexanoi caci dt ohexaneni trile (12)p- nitr
obenzoi caci dt op-
nitr
oani line
(13)benzoi caci d t o benzy lami ne (14)Benzy lalcohol to
pheny lethanoi caci d
(15)m- nitroani li
nef rom ni trobenzene (16)p- tol
udi net o2- bromo- 4-
met hy l aniline
(17)Et hanol t
o1, 2-ethanedi ol (18)Acet i
caci dt oacet aldehyde
(19)Acet icaci dt oet hy lami ne (20)acet icaci dt oacet one
(21)Benzy lalcohol toBenzoi caci d (22)Pr opanoi caci dt o
Propenoi caci d
(
23)Cy clohexenet oHexane- 1, 6-dioicaci d( 24)p- met hylacet ophenonet obenzene- 1,4-
dicarboxy l
icaci d
(25)Pr opanoy lchl oridet oDi pr opyl ami ne (26)Benzoi caci dt o
Benzal dehy de
(27)Acet ophenonet oet hy lbenzene
Q.XI# ( a)Met hyl ami net oEt hy lami neandv icev ersa (b)pr opanoi caci dt oet hy l
ammi ne
(c)et hyl bromi det o pr opanami ne (d)Acet ylchlor i
det omet hy l
chlor i
de.
IDENTI FYTHECOMPOUNDSA, B, Cet c.
1#Anor gani ccompound“ A”whi chhaschar act er
isti
codour ,ont reat mentwi thNaOHf orms
twocompounds“ B”and“ C”. Compound“ B”hasamol ecularfor mulaC7H8Owhi chonoxi dation
givesbackcompound“ A’.
Compound“ C”i st hesodi um sal tofanaci d. ”C”whenheat edwi t
hsodal imey iel dsanar omat ic
hydr ocar bon” D” .Deducet hest ruct ureA, B,C,D.
2#Anor gani ccompound“ A”hasamol ecul arf ormulaC5H10O. I
tdoesnotr educeFehl i
ng’s
Solut i
onbutf ormsabi sul phitecompound. Italsoposi t
iveiodof ormt est.Whati st hepossi ble
struct ur eof“ A” ?Expl ainy ourr easoni ngwhi chhel pedt oar r
iveatt hest r
uct ure.
3#Acompound“ A”hasamol ecul arf or mul aC5H10Ogav eaposi ti
ve2, 4-DNPt est butanegat i
ve
Tollen’ st est .
Itwasoxi di zedt ocar box yli
caci d“ B”wi thmol ecularfor mulaC3H6O2whent reat edwi t
h
alkalineKMnO4underv i
gor ouscondi tion. Sodi um sal tof‘ B”gav eahy drocar bon“ C”onKol be’
s
electrol yticr educt i
onI dent i
fyA, B andCandwr i
techemi calequat ionsf ort her eact i
on.
4#Anor gani ccompound“ A”hasamol ecul arf ormulaC3H7O2Nonr eactionwi thFeand
Conc. HCl giveacompound“ B”ofmol ecul arf ormul a C3H9N.Compound“ B”ont r
eat mentwi t
h
NaNO2andHCl giv eanot hercompound“ C”ofmol ecularf ormul aC3H8O. Thecompound“ C”
givesef fer vescencewi t
hNa. Onoxi dat ionwi thCr O3,thecompound“ C”gi vesasat ur ated
aldehy decont ainingt hreecar bonat oms. Deducet hest ructuresof “ A” ,
“ B”and“ C”andwr ite
thechemi cal equat i
onsf ort her eact i
onsi nv olved.
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