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100 j 0/F 2:; 0'( () I 2. r:. [ro.J+c; t,,, 0-- 10 f.ltdJ. ),oV/j S.J.-rt;\ 1J1rl cxlk'jl cAp!: i'g 10 2eJ1 CrOWcAeJ 5. 0/ Pt: 10ys d\\vcdo'fs 4. Br/FeBr3 OCH 3 W \'t\ S. 5+'f o "\j Ac"", W he b0 t-k C;e",-+; 0 Jv> ( o)p of\'( c*iYcc.t. www.ochemweb.com
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1J1rl - Organic Chemistry II · 2018-09-06 · 100 j 0/F2:; 0'( ~() If~'f&\ 2. r:. [ro.J+c; oJ~jJqh'iH1 t,,, ~wt . 0--jo~d W~J . 10 . f.ltdJ. ),oV/j . S.J.-rt;\ 1J1rl . cxlk'jl .

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Page 1: 1J1rl - Organic Chemistry II · 2018-09-06 · 100 j 0/F2:; 0'( ~() If~'f&\ 2. r:. [ro.J+c; oJ~jJqh'iH1 t,,, ~wt . 0--jo~d W~J . 10 . f.ltdJ. ),oV/j . S.J.-rt;\ 1J1rl . cxlk'jl .

100

j

0F2 0( ~ () I f~famp

2

r [roJ+c oJ~jJqhiH1 t ~wt 0-- jo~d W~J 10 fltdJ )oVj

SJ-rt 1J1rl cxlkjl cAp ig 10 he~ 2eJ1 emiddot

CrOWcAeJ

5

0 Pt Mer~ ~(ec10ys

dvcdofs

4

BrFeBr3

OCH3 ~ Wt S

5+foj Ac (g~ Y-es)~v)(e)

Whe ~ b0 t-k

~fe pf~ Ce-+ 0 Jvgt (

o)p of( w~u ciYcct wwwochemwebcom

8

~ stro~J ]e4CVq1by O2 0 (g1Y-(~()loq11(e)

CIJlCH3A1CI3~ No ~ cY-j t-s When 5+YO~~ eAet +y-o~ j w ~JytWn3

~(DVcf Alt- pcSe1t-

)I ~ lJe~t I M+i~+t ~ b J vtducHol1)

o)p

Dp

60 ~l1eY

H- Me+cL- dT

WVlS wwwochemwebcom

Mor~

11 I) Jones Ox ~ ~OH -

2) SOC12

3) o-ry~CH3 AICI3

o

I) CI A CH2CH3 IAlCl3 2) Zn(Hg) I HCl (aq) 3) BrjLight

f~Ytt IS M~joy b~~

+- hl+~t 5 blA1t~

1) BrlFeBr3

14 2) FmmilqIt

dllfeU1

wwwochemwebcom

15

olp C Me +(shyO)p WY~

16

1) BrLight

2) MglEtp

C ODH t1 ) exK4 (fgt-( blgt h

IT 0 2t I)H3C-C-CIA1CI )1

2) NalNH(I)lCH30H H3C-C

L

r 3)4)

I - 1 h~ Ct r bf)~s

~~ t+t tiQ1t(t1vhgt r5-- shy~ fe YerLt(~

I lf ~elfle$ AXt- r r YV eJ

+hq1shy ()e

1) CIFeCI3 NOT 2) l-INOH2SO4

19 CO Vlj u~ IlraJ 3) NaOH ( 2 eq) 1100 degC

4)Hp+

~-7 ~~)lt) AddJ1a~ - El~~1+1o~V ) O~N4J (refAIY~s ~+- D 15 1- e wen op +0 1-- Crt)

or11o l~o1Ye

wwwochemwebcom

v

2) NaOH (2 eq) 100degC 3) H30+

4) NaBHiEtOH

rp (3v-3 ) ~ilLH

J20

No ~~ 2shy

0 ~f 1shy

By

21

o 3) II

H3C-C-OH6

I) SrLight

1) NaOH (2eq)I350 C 2500 PSI

+IH

1) BrFeBr

2) MglEtO ~23

3) 0

1) 0 t

~CI +

4) H30

wwwochemwebcom

1) NaCroH2 SOL I) 2) SOC I)24middot V 3) o-SCH3 AC3

0 J VJ rs~ hv shy

~) 1-[ -C e I

I wwwochemwebcom

30

29 o

0

1) CIFeCl 2) NaOH (2 eq) 340 C 2500 PSI 3) HO+

4) Na2Cr20HSO

1) BrFeBr

2) Mget~r bull i) 1)3

C( o bDen JH~o II

H NH~ I) CICCH3 IAICI I 1 32 n 4 bull

2) Zn(Hg)IHCl (ag) o1le L1 t~o~ 3 )NaI NH(1)EtO-[ rr Nt-tp

CAY ho Vl JvJd VlJ i~ ~ ymiddot(cbtl~

~

wwwochemwebcom

33

34 CI

J)eacAmiddot1V~+0 y

35

-70 O~

BrFeBr3

~

o)pvsN~~

Op WlhS

~ _ CtAt ho~ hAY Aj 8W6i ~tl ~ coV b)~ Of~osJk

+tgt ~ fAye lttiS-M (e

36 1h~ C~rbo~ ~

pound WUt k -~ (p bo 1

1fjJo~Jf J-traquo CAYC

Y~-cg(

C ~ ) 6 J)lrt 5 No r 1eJu(~o

37

+ CI~J

ampWCn is Nor

~ ec+1 -fD JAt(A)11 yt (Cffd

r~J -hgt WI i41iytt w hy wwwochemwebcom

re ~o ~l1 ce (lie do) CYQit~ WIV t- Aergte

38

0 ) gy-~ JFe BYl vr39

2-) AIJ Jlit2 0

H

3) A Htr~ 113 0 1shy

4) peL JCH-Uz

40 lt-OCH3

2) HPt 3) Jones Ox 4) SOClz

5) Br

rl SCH3 IAICI 3u--l

41 ~

5hoVje ~gt UI( lAc h laquo-1-0 (

wwwochemwebcom

1) NaOH ( 2 eg) 100 degC ~ 42

CI

CI

1) BfFeBr3

44

0 1) KMnOOHlHzOl 100degC 2) H+ 45

3) o-OH W

4) HNOH2S04

) ~ lt_r-0

Oli ~

-7

~)

wwwochemwebcom

47

DaJv AQri3

Br~ r3r~ p By 3) Yl ( H~) JH(1 (CA~) Br

4) NG~)hv J) -+0- r 6) HSy- f CH3 00 cH3

I)Q~ALU~0 lt) ZY) (H~) ) HU (CfbJ

3) u~) A1U3 Hy 2-~ Crt) ) Hu LfJ1I)

oyo1 (-r- l~ le~J iMf

fr fJOi-~ P(I) ceZ JA1-~3 Ilnr ~ No F [-Iti) HND3 JH~lt0+) fj

CI N02 rl U2- ~ pl4+shy3) C1- JPeJmiddotmiddot~3 tITJ-t-) 1- W014 Jj

tA -rc c-1 01f seyJ

ttmiddotmiddot wt~ CI 1) NaOH ( 2 eq) I 350degC I 2500 PSI

- n ] -O~ ~

o

_OJ

so CI-) lt ) ~ 7

503H j)

1shysty)) l)e4chv~-toy

a I IVI I S f ~ j wwwochemwebcom

b re ~ 0 Ilt) ~ Ce -J) IN mOre

de (t c+f ~ +e c

~6

~l 1) = IAICICI 3

51 o-~OCH3 2) HNOH2S04

3) N~NHJKOH~

4) NaINHCH30II~ I)

I) C~ JMIlJ520 i) r-J4 SWl() Gt-DH

3) Noshy4-) ~6y

oj

Br

1) NOH (20) 100deg I)53

2) CH3Br

3) BrJFeBrJ N0z- 3)

--7 2)

I) a~ fWJj DN

~) 2 () ( Kj)i HCi(t~-) 3) HNO IH2~DLf

wwwochemwebcom

We4K YltHmiddot k pro +L 11~ CHpHl Y 1shyH0lt~ ~CJ- gtr-J

(fi-)

CI C~L S--r Ot3

6 ) lt IHF

CI 55 2)~ IAICI

1)1 o 3

~+

3) Zn(Hg)HCI(ag) a 4) NBShv

CJ- GL lJt) 51rD~J

7 aOlse 0 2- 0

2) ~)

6 OH OH

~ 56

BF3

+ Q~ CI

N02 H NLH3

C~NHi 57 centrN0

l~ 2shy

N02

N02shy

CI

58 NaOH (2 eg)1 3500CI 2500 PSI

No HJ~yrJevt to e dYpound1Vt~ fed for- forwtq-HoshyfY be VJ ~ V1 e wwwochemwebcom

Page 2: 1J1rl - Organic Chemistry II · 2018-09-06 · 100 j 0/F2:; 0'( ~() If~'f&\ 2. r:. [ro.J+c; oJ~jJqh'iH1 t,,, ~wt . 0--jo~d W~J . 10 . f.ltdJ. ),oV/j . S.J.-rt;\ 1J1rl . cxlk'jl .

8

~ stro~J ]e4CVq1by O2 0 (g1Y-(~()loq11(e)

CIJlCH3A1CI3~ No ~ cY-j t-s When 5+YO~~ eAet +y-o~ j w ~JytWn3

~(DVcf Alt- pcSe1t-

)I ~ lJe~t I M+i~+t ~ b J vtducHol1)

o)p

Dp

60 ~l1eY

H- Me+cL- dT

WVlS wwwochemwebcom

Mor~

11 I) Jones Ox ~ ~OH -

2) SOC12

3) o-ry~CH3 AICI3

o

I) CI A CH2CH3 IAlCl3 2) Zn(Hg) I HCl (aq) 3) BrjLight

f~Ytt IS M~joy b~~

+- hl+~t 5 blA1t~

1) BrlFeBr3

14 2) FmmilqIt

dllfeU1

wwwochemwebcom

15

olp C Me +(shyO)p WY~

16

1) BrLight

2) MglEtp

C ODH t1 ) exK4 (fgt-( blgt h

IT 0 2t I)H3C-C-CIA1CI )1

2) NalNH(I)lCH30H H3C-C

L

r 3)4)

I - 1 h~ Ct r bf)~s

~~ t+t tiQ1t(t1vhgt r5-- shy~ fe YerLt(~

I lf ~elfle$ AXt- r r YV eJ

+hq1shy ()e

1) CIFeCI3 NOT 2) l-INOH2SO4

19 CO Vlj u~ IlraJ 3) NaOH ( 2 eq) 1100 degC

4)Hp+

~-7 ~~)lt) AddJ1a~ - El~~1+1o~V ) O~N4J (refAIY~s ~+- D 15 1- e wen op +0 1-- Crt)

or11o l~o1Ye

wwwochemwebcom

v

2) NaOH (2 eq) 100degC 3) H30+

4) NaBHiEtOH

rp (3v-3 ) ~ilLH

J20

No ~~ 2shy

0 ~f 1shy

By

21

o 3) II

H3C-C-OH6

I) SrLight

1) NaOH (2eq)I350 C 2500 PSI

+IH

1) BrFeBr

2) MglEtO ~23

3) 0

1) 0 t

~CI +

4) H30

wwwochemwebcom

1) NaCroH2 SOL I) 2) SOC I)24middot V 3) o-SCH3 AC3

0 J VJ rs~ hv shy

~) 1-[ -C e I

I wwwochemwebcom

30

29 o

0

1) CIFeCl 2) NaOH (2 eq) 340 C 2500 PSI 3) HO+

4) Na2Cr20HSO

1) BrFeBr

2) Mget~r bull i) 1)3

C( o bDen JH~o II

H NH~ I) CICCH3 IAICI I 1 32 n 4 bull

2) Zn(Hg)IHCl (ag) o1le L1 t~o~ 3 )NaI NH(1)EtO-[ rr Nt-tp

CAY ho Vl JvJd VlJ i~ ~ ymiddot(cbtl~

~

wwwochemwebcom

33

34 CI

J)eacAmiddot1V~+0 y

35

-70 O~

BrFeBr3

~

o)pvsN~~

Op WlhS

~ _ CtAt ho~ hAY Aj 8W6i ~tl ~ coV b)~ Of~osJk

+tgt ~ fAye lttiS-M (e

36 1h~ C~rbo~ ~

pound WUt k -~ (p bo 1

1fjJo~Jf J-traquo CAYC

Y~-cg(

C ~ ) 6 J)lrt 5 No r 1eJu(~o

37

+ CI~J

ampWCn is Nor

~ ec+1 -fD JAt(A)11 yt (Cffd

r~J -hgt WI i41iytt w hy wwwochemwebcom

re ~o ~l1 ce (lie do) CYQit~ WIV t- Aergte

38

0 ) gy-~ JFe BYl vr39

2-) AIJ Jlit2 0

H

3) A Htr~ 113 0 1shy

4) peL JCH-Uz

40 lt-OCH3

2) HPt 3) Jones Ox 4) SOClz

5) Br

rl SCH3 IAICI 3u--l

41 ~

5hoVje ~gt UI( lAc h laquo-1-0 (

wwwochemwebcom

1) NaOH ( 2 eg) 100 degC ~ 42

CI

CI

1) BfFeBr3

44

0 1) KMnOOHlHzOl 100degC 2) H+ 45

3) o-OH W

4) HNOH2S04

) ~ lt_r-0

Oli ~

-7

~)

wwwochemwebcom

47

DaJv AQri3

Br~ r3r~ p By 3) Yl ( H~) JH(1 (CA~) Br

4) NG~)hv J) -+0- r 6) HSy- f CH3 00 cH3

I)Q~ALU~0 lt) ZY) (H~) ) HU (CfbJ

3) u~) A1U3 Hy 2-~ Crt) ) Hu LfJ1I)

oyo1 (-r- l~ le~J iMf

fr fJOi-~ P(I) ceZ JA1-~3 Ilnr ~ No F [-Iti) HND3 JH~lt0+) fj

CI N02 rl U2- ~ pl4+shy3) C1- JPeJmiddotmiddot~3 tITJ-t-) 1- W014 Jj

tA -rc c-1 01f seyJ

ttmiddotmiddot wt~ CI 1) NaOH ( 2 eq) I 350degC I 2500 PSI

- n ] -O~ ~

o

_OJ

so CI-) lt ) ~ 7

503H j)

1shysty)) l)e4chv~-toy

a I IVI I S f ~ j wwwochemwebcom

b re ~ 0 Ilt) ~ Ce -J) IN mOre

de (t c+f ~ +e c

~6

~l 1) = IAICICI 3

51 o-~OCH3 2) HNOH2S04

3) N~NHJKOH~

4) NaINHCH30II~ I)

I) C~ JMIlJ520 i) r-J4 SWl() Gt-DH

3) Noshy4-) ~6y

oj

Br

1) NOH (20) 100deg I)53

2) CH3Br

3) BrJFeBrJ N0z- 3)

--7 2)

I) a~ fWJj DN

~) 2 () ( Kj)i HCi(t~-) 3) HNO IH2~DLf

wwwochemwebcom

We4K YltHmiddot k pro +L 11~ CHpHl Y 1shyH0lt~ ~CJ- gtr-J

(fi-)

CI C~L S--r Ot3

6 ) lt IHF

CI 55 2)~ IAICI

1)1 o 3

~+

3) Zn(Hg)HCI(ag) a 4) NBShv

CJ- GL lJt) 51rD~J

7 aOlse 0 2- 0

2) ~)

6 OH OH

~ 56

BF3

+ Q~ CI

N02 H NLH3

C~NHi 57 centrN0

l~ 2shy

N02

N02shy

CI

58 NaOH (2 eg)1 3500CI 2500 PSI

No HJ~yrJevt to e dYpound1Vt~ fed for- forwtq-HoshyfY be VJ ~ V1 e wwwochemwebcom

Page 3: 1J1rl - Organic Chemistry II · 2018-09-06 · 100 j 0/F2:; 0'( ~() If~'f&\ 2. r:. [ro.J+c; oJ~jJqh'iH1 t,,, ~wt . 0--jo~d W~J . 10 . f.ltdJ. ),oV/j . S.J.-rt;\ 1J1rl . cxlk'jl .

Mor~

11 I) Jones Ox ~ ~OH -

2) SOC12

3) o-ry~CH3 AICI3

o

I) CI A CH2CH3 IAlCl3 2) Zn(Hg) I HCl (aq) 3) BrjLight

f~Ytt IS M~joy b~~

+- hl+~t 5 blA1t~

1) BrlFeBr3

14 2) FmmilqIt

dllfeU1

wwwochemwebcom

15

olp C Me +(shyO)p WY~

16

1) BrLight

2) MglEtp

C ODH t1 ) exK4 (fgt-( blgt h

IT 0 2t I)H3C-C-CIA1CI )1

2) NalNH(I)lCH30H H3C-C

L

r 3)4)

I - 1 h~ Ct r bf)~s

~~ t+t tiQ1t(t1vhgt r5-- shy~ fe YerLt(~

I lf ~elfle$ AXt- r r YV eJ

+hq1shy ()e

1) CIFeCI3 NOT 2) l-INOH2SO4

19 CO Vlj u~ IlraJ 3) NaOH ( 2 eq) 1100 degC

4)Hp+

~-7 ~~)lt) AddJ1a~ - El~~1+1o~V ) O~N4J (refAIY~s ~+- D 15 1- e wen op +0 1-- Crt)

or11o l~o1Ye

wwwochemwebcom

v

2) NaOH (2 eq) 100degC 3) H30+

4) NaBHiEtOH

rp (3v-3 ) ~ilLH

J20

No ~~ 2shy

0 ~f 1shy

By

21

o 3) II

H3C-C-OH6

I) SrLight

1) NaOH (2eq)I350 C 2500 PSI

+IH

1) BrFeBr

2) MglEtO ~23

3) 0

1) 0 t

~CI +

4) H30

wwwochemwebcom

1) NaCroH2 SOL I) 2) SOC I)24middot V 3) o-SCH3 AC3

0 J VJ rs~ hv shy

~) 1-[ -C e I

I wwwochemwebcom

30

29 o

0

1) CIFeCl 2) NaOH (2 eq) 340 C 2500 PSI 3) HO+

4) Na2Cr20HSO

1) BrFeBr

2) Mget~r bull i) 1)3

C( o bDen JH~o II

H NH~ I) CICCH3 IAICI I 1 32 n 4 bull

2) Zn(Hg)IHCl (ag) o1le L1 t~o~ 3 )NaI NH(1)EtO-[ rr Nt-tp

CAY ho Vl JvJd VlJ i~ ~ ymiddot(cbtl~

~

wwwochemwebcom

33

34 CI

J)eacAmiddot1V~+0 y

35

-70 O~

BrFeBr3

~

o)pvsN~~

Op WlhS

~ _ CtAt ho~ hAY Aj 8W6i ~tl ~ coV b)~ Of~osJk

+tgt ~ fAye lttiS-M (e

36 1h~ C~rbo~ ~

pound WUt k -~ (p bo 1

1fjJo~Jf J-traquo CAYC

Y~-cg(

C ~ ) 6 J)lrt 5 No r 1eJu(~o

37

+ CI~J

ampWCn is Nor

~ ec+1 -fD JAt(A)11 yt (Cffd

r~J -hgt WI i41iytt w hy wwwochemwebcom

re ~o ~l1 ce (lie do) CYQit~ WIV t- Aergte

38

0 ) gy-~ JFe BYl vr39

2-) AIJ Jlit2 0

H

3) A Htr~ 113 0 1shy

4) peL JCH-Uz

40 lt-OCH3

2) HPt 3) Jones Ox 4) SOClz

5) Br

rl SCH3 IAICI 3u--l

41 ~

5hoVje ~gt UI( lAc h laquo-1-0 (

wwwochemwebcom

1) NaOH ( 2 eg) 100 degC ~ 42

CI

CI

1) BfFeBr3

44

0 1) KMnOOHlHzOl 100degC 2) H+ 45

3) o-OH W

4) HNOH2S04

) ~ lt_r-0

Oli ~

-7

~)

wwwochemwebcom

47

DaJv AQri3

Br~ r3r~ p By 3) Yl ( H~) JH(1 (CA~) Br

4) NG~)hv J) -+0- r 6) HSy- f CH3 00 cH3

I)Q~ALU~0 lt) ZY) (H~) ) HU (CfbJ

3) u~) A1U3 Hy 2-~ Crt) ) Hu LfJ1I)

oyo1 (-r- l~ le~J iMf

fr fJOi-~ P(I) ceZ JA1-~3 Ilnr ~ No F [-Iti) HND3 JH~lt0+) fj

CI N02 rl U2- ~ pl4+shy3) C1- JPeJmiddotmiddot~3 tITJ-t-) 1- W014 Jj

tA -rc c-1 01f seyJ

ttmiddotmiddot wt~ CI 1) NaOH ( 2 eq) I 350degC I 2500 PSI

- n ] -O~ ~

o

_OJ

so CI-) lt ) ~ 7

503H j)

1shysty)) l)e4chv~-toy

a I IVI I S f ~ j wwwochemwebcom

b re ~ 0 Ilt) ~ Ce -J) IN mOre

de (t c+f ~ +e c

~6

~l 1) = IAICICI 3

51 o-~OCH3 2) HNOH2S04

3) N~NHJKOH~

4) NaINHCH30II~ I)

I) C~ JMIlJ520 i) r-J4 SWl() Gt-DH

3) Noshy4-) ~6y

oj

Br

1) NOH (20) 100deg I)53

2) CH3Br

3) BrJFeBrJ N0z- 3)

--7 2)

I) a~ fWJj DN

~) 2 () ( Kj)i HCi(t~-) 3) HNO IH2~DLf

wwwochemwebcom

We4K YltHmiddot k pro +L 11~ CHpHl Y 1shyH0lt~ ~CJ- gtr-J

(fi-)

CI C~L S--r Ot3

6 ) lt IHF

CI 55 2)~ IAICI

1)1 o 3

~+

3) Zn(Hg)HCI(ag) a 4) NBShv

CJ- GL lJt) 51rD~J

7 aOlse 0 2- 0

2) ~)

6 OH OH

~ 56

BF3

+ Q~ CI

N02 H NLH3

C~NHi 57 centrN0

l~ 2shy

N02

N02shy

CI

58 NaOH (2 eg)1 3500CI 2500 PSI

No HJ~yrJevt to e dYpound1Vt~ fed for- forwtq-HoshyfY be VJ ~ V1 e wwwochemwebcom

Page 4: 1J1rl - Organic Chemistry II · 2018-09-06 · 100 j 0/F2:; 0'( ~() If~'f&\ 2. r:. [ro.J+c; oJ~jJqh'iH1 t,,, ~wt . 0--jo~d W~J . 10 . f.ltdJ. ),oV/j . S.J.-rt;\ 1J1rl . cxlk'jl .

15

olp C Me +(shyO)p WY~

16

1) BrLight

2) MglEtp

C ODH t1 ) exK4 (fgt-( blgt h

IT 0 2t I)H3C-C-CIA1CI )1

2) NalNH(I)lCH30H H3C-C

L

r 3)4)

I - 1 h~ Ct r bf)~s

~~ t+t tiQ1t(t1vhgt r5-- shy~ fe YerLt(~

I lf ~elfle$ AXt- r r YV eJ

+hq1shy ()e

1) CIFeCI3 NOT 2) l-INOH2SO4

19 CO Vlj u~ IlraJ 3) NaOH ( 2 eq) 1100 degC

4)Hp+

~-7 ~~)lt) AddJ1a~ - El~~1+1o~V ) O~N4J (refAIY~s ~+- D 15 1- e wen op +0 1-- Crt)

or11o l~o1Ye

wwwochemwebcom

v

2) NaOH (2 eq) 100degC 3) H30+

4) NaBHiEtOH

rp (3v-3 ) ~ilLH

J20

No ~~ 2shy

0 ~f 1shy

By

21

o 3) II

H3C-C-OH6

I) SrLight

1) NaOH (2eq)I350 C 2500 PSI

+IH

1) BrFeBr

2) MglEtO ~23

3) 0

1) 0 t

~CI +

4) H30

wwwochemwebcom

1) NaCroH2 SOL I) 2) SOC I)24middot V 3) o-SCH3 AC3

0 J VJ rs~ hv shy

~) 1-[ -C e I

I wwwochemwebcom

30

29 o

0

1) CIFeCl 2) NaOH (2 eq) 340 C 2500 PSI 3) HO+

4) Na2Cr20HSO

1) BrFeBr

2) Mget~r bull i) 1)3

C( o bDen JH~o II

H NH~ I) CICCH3 IAICI I 1 32 n 4 bull

2) Zn(Hg)IHCl (ag) o1le L1 t~o~ 3 )NaI NH(1)EtO-[ rr Nt-tp

CAY ho Vl JvJd VlJ i~ ~ ymiddot(cbtl~

~

wwwochemwebcom

33

34 CI

J)eacAmiddot1V~+0 y

35

-70 O~

BrFeBr3

~

o)pvsN~~

Op WlhS

~ _ CtAt ho~ hAY Aj 8W6i ~tl ~ coV b)~ Of~osJk

+tgt ~ fAye lttiS-M (e

36 1h~ C~rbo~ ~

pound WUt k -~ (p bo 1

1fjJo~Jf J-traquo CAYC

Y~-cg(

C ~ ) 6 J)lrt 5 No r 1eJu(~o

37

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30

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1) NaOH ( 2 eg) 100 degC ~ 42

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~+

3) Zn(Hg)HCI(ag) a 4) NBShv

CJ- GL lJt) 51rD~J

7 aOlse 0 2- 0

2) ~)

6 OH OH

~ 56

BF3

+ Q~ CI

N02 H NLH3

C~NHi 57 centrN0

l~ 2shy

N02

N02shy

CI

58 NaOH (2 eg)1 3500CI 2500 PSI

No HJ~yrJevt to e dYpound1Vt~ fed for- forwtq-HoshyfY be VJ ~ V1 e wwwochemwebcom

Page 10: 1J1rl - Organic Chemistry II · 2018-09-06 · 100 j 0/F2:; 0'( ~() If~'f&\ 2. r:. [ro.J+c; oJ~jJqh'iH1 t,,, ~wt . 0--jo~d W~J . 10 . f.ltdJ. ),oV/j . S.J.-rt;\ 1J1rl . cxlk'jl .

1) NaOH ( 2 eg) 100 degC ~ 42

CI

CI

1) BfFeBr3

44

0 1) KMnOOHlHzOl 100degC 2) H+ 45

3) o-OH W

4) HNOH2S04

) ~ lt_r-0

Oli ~

-7

~)

wwwochemwebcom

47

DaJv AQri3

Br~ r3r~ p By 3) Yl ( H~) JH(1 (CA~) Br

4) NG~)hv J) -+0- r 6) HSy- f CH3 00 cH3

I)Q~ALU~0 lt) ZY) (H~) ) HU (CfbJ

3) u~) A1U3 Hy 2-~ Crt) ) Hu LfJ1I)

oyo1 (-r- l~ le~J iMf

fr fJOi-~ P(I) ceZ JA1-~3 Ilnr ~ No F [-Iti) HND3 JH~lt0+) fj

CI N02 rl U2- ~ pl4+shy3) C1- JPeJmiddotmiddot~3 tITJ-t-) 1- W014 Jj

tA -rc c-1 01f seyJ

ttmiddotmiddot wt~ CI 1) NaOH ( 2 eq) I 350degC I 2500 PSI

- n ] -O~ ~

o

_OJ

so CI-) lt ) ~ 7

503H j)

1shysty)) l)e4chv~-toy

a I IVI I S f ~ j wwwochemwebcom

b re ~ 0 Ilt) ~ Ce -J) IN mOre

de (t c+f ~ +e c

~6

~l 1) = IAICICI 3

51 o-~OCH3 2) HNOH2S04

3) N~NHJKOH~

4) NaINHCH30II~ I)

I) C~ JMIlJ520 i) r-J4 SWl() Gt-DH

3) Noshy4-) ~6y

oj

Br

1) NOH (20) 100deg I)53

2) CH3Br

3) BrJFeBrJ N0z- 3)

--7 2)

I) a~ fWJj DN

~) 2 () ( Kj)i HCi(t~-) 3) HNO IH2~DLf

wwwochemwebcom

We4K YltHmiddot k pro +L 11~ CHpHl Y 1shyH0lt~ ~CJ- gtr-J

(fi-)

CI C~L S--r Ot3

6 ) lt IHF

CI 55 2)~ IAICI

1)1 o 3

~+

3) Zn(Hg)HCI(ag) a 4) NBShv

CJ- GL lJt) 51rD~J

7 aOlse 0 2- 0

2) ~)

6 OH OH

~ 56

BF3

+ Q~ CI

N02 H NLH3

C~NHi 57 centrN0

l~ 2shy

N02

N02shy

CI

58 NaOH (2 eg)1 3500CI 2500 PSI

No HJ~yrJevt to e dYpound1Vt~ fed for- forwtq-HoshyfY be VJ ~ V1 e wwwochemwebcom

Page 11: 1J1rl - Organic Chemistry II · 2018-09-06 · 100 j 0/F2:; 0'( ~() If~'f&\ 2. r:. [ro.J+c; oJ~jJqh'iH1 t,,, ~wt . 0--jo~d W~J . 10 . f.ltdJ. ),oV/j . S.J.-rt;\ 1J1rl . cxlk'jl .

47

DaJv AQri3

Br~ r3r~ p By 3) Yl ( H~) JH(1 (CA~) Br

4) NG~)hv J) -+0- r 6) HSy- f CH3 00 cH3

I)Q~ALU~0 lt) ZY) (H~) ) HU (CfbJ

3) u~) A1U3 Hy 2-~ Crt) ) Hu LfJ1I)

oyo1 (-r- l~ le~J iMf

fr fJOi-~ P(I) ceZ JA1-~3 Ilnr ~ No F [-Iti) HND3 JH~lt0+) fj

CI N02 rl U2- ~ pl4+shy3) C1- JPeJmiddotmiddot~3 tITJ-t-) 1- W014 Jj

tA -rc c-1 01f seyJ

ttmiddotmiddot wt~ CI 1) NaOH ( 2 eq) I 350degC I 2500 PSI

- n ] -O~ ~

o

_OJ

so CI-) lt ) ~ 7

503H j)

1shysty)) l)e4chv~-toy

a I IVI I S f ~ j wwwochemwebcom

b re ~ 0 Ilt) ~ Ce -J) IN mOre

de (t c+f ~ +e c

~6

~l 1) = IAICICI 3

51 o-~OCH3 2) HNOH2S04

3) N~NHJKOH~

4) NaINHCH30II~ I)

I) C~ JMIlJ520 i) r-J4 SWl() Gt-DH

3) Noshy4-) ~6y

oj

Br

1) NOH (20) 100deg I)53

2) CH3Br

3) BrJFeBrJ N0z- 3)

--7 2)

I) a~ fWJj DN

~) 2 () ( Kj)i HCi(t~-) 3) HNO IH2~DLf

wwwochemwebcom

We4K YltHmiddot k pro +L 11~ CHpHl Y 1shyH0lt~ ~CJ- gtr-J

(fi-)

CI C~L S--r Ot3

6 ) lt IHF

CI 55 2)~ IAICI

1)1 o 3

~+

3) Zn(Hg)HCI(ag) a 4) NBShv

CJ- GL lJt) 51rD~J

7 aOlse 0 2- 0

2) ~)

6 OH OH

~ 56

BF3

+ Q~ CI

N02 H NLH3

C~NHi 57 centrN0

l~ 2shy

N02

N02shy

CI

58 NaOH (2 eg)1 3500CI 2500 PSI

No HJ~yrJevt to e dYpound1Vt~ fed for- forwtq-HoshyfY be VJ ~ V1 e wwwochemwebcom

Page 12: 1J1rl - Organic Chemistry II · 2018-09-06 · 100 j 0/F2:; 0'( ~() If~'f&\ 2. r:. [ro.J+c; oJ~jJqh'iH1 t,,, ~wt . 0--jo~d W~J . 10 . f.ltdJ. ),oV/j . S.J.-rt;\ 1J1rl . cxlk'jl .

~l 1) = IAICICI 3

51 o-~OCH3 2) HNOH2S04

3) N~NHJKOH~

4) NaINHCH30II~ I)

I) C~ JMIlJ520 i) r-J4 SWl() Gt-DH

3) Noshy4-) ~6y

oj

Br

1) NOH (20) 100deg I)53

2) CH3Br

3) BrJFeBrJ N0z- 3)

--7 2)

I) a~ fWJj DN

~) 2 () ( Kj)i HCi(t~-) 3) HNO IH2~DLf

wwwochemwebcom

We4K YltHmiddot k pro +L 11~ CHpHl Y 1shyH0lt~ ~CJ- gtr-J

(fi-)

CI C~L S--r Ot3

6 ) lt IHF

CI 55 2)~ IAICI

1)1 o 3

~+

3) Zn(Hg)HCI(ag) a 4) NBShv

CJ- GL lJt) 51rD~J

7 aOlse 0 2- 0

2) ~)

6 OH OH

~ 56

BF3

+ Q~ CI

N02 H NLH3

C~NHi 57 centrN0

l~ 2shy

N02

N02shy

CI

58 NaOH (2 eg)1 3500CI 2500 PSI

No HJ~yrJevt to e dYpound1Vt~ fed for- forwtq-HoshyfY be VJ ~ V1 e wwwochemwebcom

Page 13: 1J1rl - Organic Chemistry II · 2018-09-06 · 100 j 0/F2:; 0'( ~() If~'f&\ 2. r:. [ro.J+c; oJ~jJqh'iH1 t,,, ~wt . 0--jo~d W~J . 10 . f.ltdJ. ),oV/j . S.J.-rt;\ 1J1rl . cxlk'jl .

We4K YltHmiddot k pro +L 11~ CHpHl Y 1shyH0lt~ ~CJ- gtr-J

(fi-)

CI C~L S--r Ot3

6 ) lt IHF

CI 55 2)~ IAICI

1)1 o 3

~+

3) Zn(Hg)HCI(ag) a 4) NBShv

CJ- GL lJt) 51rD~J

7 aOlse 0 2- 0

2) ~)

6 OH OH

~ 56

BF3

+ Q~ CI

N02 H NLH3

C~NHi 57 centrN0

l~ 2shy

N02

N02shy

CI

58 NaOH (2 eg)1 3500CI 2500 PSI

No HJ~yrJevt to e dYpound1Vt~ fed for- forwtq-HoshyfY be VJ ~ V1 e wwwochemwebcom