c) (CH ~ ) ! CIHJ-I ( Of-i ) CH1. (1..

3 1

3d)

PENTANOW

Z '-(,[,oKo - 3 -

PENfANOLD

2 -MEnL - 3 - PENfANOLe>

(Hs (H

Ue.)

U11 O~ (OH) lH~

PfNfANOW

4 - (1-0 ((0 - Z. Q._) 1, L- DIMtTlL

013
I
I

ts,(lO t,L~; 5U'III-{t_

l.t rrMvLc eli.

b)

S~(\I!iL)(Q..oltA.. ~(){(lt
0-

t.O~poll q 2,3OH
I

.- A - BUTANOW

C~3 0-11 c - (U1 -Of.{

(H~
~) HOSSIOO 01 ~ODi 0

OBr
01-1

BKONlOfENOLo

PENfANDIOLO

d)

7... -FfNIUTA-NOLO

0-13 CH CH CH 1CH J

OH

S)

A-MEnL.CILLOPfNTANOLQ

%)

tro..M- 2-METILtllLOPENTANOLO

01-1
(H~

Ol-l

h-)
_

(K)-I-BUTANOL.O

I) Z-MEnL -1W
C~Z ~

PlloPfN -If- OLD

l .

CHJ

l) L -(lLLOfSANOLO

014
C~J(H (H~(HJ

CQ,d I;

(H, -

OH
J

.2- '1I>.. ~
t,L
WIY\L pnl'llQ_(j ,

'\t---\
~

ts.n.° 1.l6;
h.)

(1w.trtA.rt

1l Qlwli
d) ALLOL

I( I~

11) MwL. PRIMArtlO

ALLOL SHDNM~IO

PIZIMAf..IO

n
L)

kwn..clo..(i

0 h.Hio..ri .

ALLOL TERtIA~IO
ALLOL SEtoN DARIO

~) ALWL

SEWNDAIZIO

i) AlcoL PKIMA~IO

b .11..0 8 ,A~:
OH GI~~
I

SU\vi IA. ~rmolo..

cL:. ~hvILLl(o.. d.tA, ~ve.tL~ a..ltolA.

PWPILENIW

d)
i-METIL -l-PWPIL--i,S-PP.oPANDIOW LHS

0...) AlwllsoPrtoPILlW

b) qUC'()lE

t)

5-Mffll-~-ESANOLO

Oli
I

OH
I

LH3
I

OH
I

(.H3

C~~- (~ - LH~

C~3 LH (HI. CH1. (1-1 LH)

~o- C~ C 0-1 t - OH
Ut1. O-lt (H 3
I

e) 1,7._ - DiMETI L ~ --1- P(O PANOI..O

n l-MH ..(APrOETANOLO
i)

CH)
f

(H5-~-(H2-0H

(1;5

h.) ~ -METlL -1.- EStN - A - OLD

(H$
I

cH-3-PrNfEN-A-OLO

l)

hClI1~

-A, ~-

ClLLOt)AN()IOW

H"
(Ht(H::;.

CH3 (H

CHCi'hoH
/

C=(

/~
"

OH

OH

Es . Ita t. n: A~~€~l\.O.h.. illw\\1JL

G-) lJ~L(cH))llH(OH)lH~

~t3~-{(tt

WMfo~t:

b) CH5(H(Br)((CH3)z_O~

ceAce
(e
2,4,6 - WlLwIWfENOLO %)
tH3LH
:=;

OH

d)

(ILloPltO PAtvOW

(t\-

B((ONWffNOLO

Osr
o.i

OH

(H CHLOI-l

~-BUTEN -.A -OLO

z-

2-MHJAfroPflOPANO PIWPANT\o~o

.~,"l,314 - BurAIIlTET1AOLO
1OIVIposl

P«OPOSSfOO

01 POfAS510

fROPllATO DI PorA~~IO
1e~Ir{!\-t:

Es.l\.° g,A3: .As~1\O. il I\..OMt

e.)
lI-l3LHtLHl(HILH10H

b)

~OCHl.LHlLHl.OH

11- PENTA NOLo e) O~

H~

.-1,3- PROPANDIOu)

3- BOTEN -;1- ow
)
Q

f)

CH3LHl ll-h lHL - Stl

~- BOrAN

noto

00,=\
CH3

3-NlfTiL - --1- BUfANOLO

b) ( LH~) s C 0 ~
L-MtnL

ALloL ten-BUTIUW -7.. - PIWPAIVOLO

cis- All-uUOE~ANDIOLO
t)

A==-/\./
4 - fPTFN - 3'-OLo

OH

Otl

.~-M€TIL-.-i-LIUOE~NOLO

d)~
CI(L 0 PENTA NO L.O

CI ~ -

Q)

1120 Q\id.o pio hlolt

(A.(j.M pio ~(b..

~LW3

--)

~W3

10_'
CI-I5(07,-

b)

CH30l-\ ) fkl3 c'o'LH --') QU.clo piO dJ.bou. Q.uM piO ~(11

CH3- C -01 H, H I
I

1I.p. e

101

-G
I
::=

CI13 - C

0/

:"-.

t) lH~(j.jtOH
a.o_d,o

) CJ.l3CI.l1SH -') P'IV dLbo~ QLiM plu So(tt.

CH3U11.S

I-1-C-('-51

H/

( pi0 ~ft. '11 nOALwL ckU' ALLOL ~(d\i cu.i,v(l. daLLo.. dt.proi:oll..o.:t(OI\L clLll' a.u.do solf<,d(,w.

1-1

ALLO L

TlOALlOl,.

ALIDO ALETIW

Q.) OH-

(~pi0 Q.ii,clo
I

H-o - H

~:tL

Gl30ba.K p-,v cLtbolt

-';>

pen.1-J.
~t.:vQ.

ri<£1It uui(.Q..

e:

ro..G~cw-t-o.

per

i~:tiorLL

k,

3 Id(ocy~ / 9w..1I.A1. l<.. (,Q/,t.Q...

t lo,

So(l'1\ulo.. [ ~lAb',L;.H:Q.6. (piC d.t.bol.L )

b)

lH3U'hSbo.t,{. p'lo dJ_~olL

(,H~ 0-11. 0

bo.~ P-IO Wrti

-)

o..c.i,clo LOrU.V~to

CH} CH10H

c) U13CH10-

bas-<.. pIG" cltbolL

NH1-) bru<.pivhrtL -)

o..v.d..o l.OM.v~to : NH,3 e uru.. blll-t d-i. Le.v.il~ molto

~(rJ~

~rdJ. ~ 1 d.opp-ldL. cL elJ.ti.ro~

dA.OloM:<.te.

D.- )

bo.~ fofk
10\

(1-13 0410

l~3W10H +- Ita.u:.clo dlbou. kK cL.boLt

b)

II

013 C O~ Qilclo ~(tx.

prtd.J__0.. \.0..
+-

+ Ul3()-1t.OH o~<icLo <hbolt.

E~- 8. Yl'
(to

r)~lIOr\Jl

<k

9ui.u.bno
--':>

~(U.Q.~VJI\,Q__

li.Q.~iol\L
t

cui-d.-v -lxu-t.
Qlid.o p-,J ~(ti.

<1-) CH3UhOH Q.<id.o cltbou.

NQ4-0H -

bo.M d.t~LL No_+OH~~ ~(tt.

(H~LH1.5 - Na.+ 10'

GIs U--I1.0 No,

001-(. ~(U. li-l3LH1S-IJl+ ba.K dtbo LL

+-

~lO

b)
c.)

Qu.cJ.c ~(k

tHs CH1SH

1-

+- HLO

ll.Litio ck 00 It.

(~3(Hl.OH

dshllt

~ (H3 CHI 0 - No. +

~K

.).

kf..{. d.tbclt..
+
1\

~(b..
II

o.u.c1.o ~(tt
10 '

LH3 u-t1SH

d)

U--\3LHtS-No.+ bat,{. ~(tt

lU.i.cLo

W3(,OH
~f

U.

......

===--?" lH3 (}-It.~H + U/s c 0-NC/ \xlI{ d.t~lL w.A.cLo ddx)lt.

0,,)
o

IZ- OH ==;

RJ(

ol.cYfiWro

oJL\V..kw

.;i moJ..o;
lYIeLlQO-1 SoMO :

IZ -01-1

+ HX ~

K-o-H

-~@

+H

~~~e IZ.-O-~-Ol

-'>

-')

b)

R-OH e-:')

~-c-o:-(\
-

10'

I~I
e~ttr<--/0'

R. -OH ~ CHs WaH

tf\H l4..I\\ ~~ IO'~
II 0: :}

--~

Hl~O£,

u.ts C. -2
II

- (l

01~ (. - Q_ -f-ot l-I

I

+ 1-1

101
I

-'>~~-~-Q-~
lOl-

+-

Qlido lO...(bo~~i

10'
c) ~-

OH ~

IZ- c. - OH

j!

tiw

Es. e%· 4
A.

ProPO(1'{

i I'InQ.LLULM.SN\i

Yt\.l(UJA cL..lL..
~l;.
61/

ttu.·llOM.

jdro..~-l:io{\i.

cu;.olo - w..kU.~:HL.tu.

Qkh.t~

,~~+
/'

c=(

H -)

H,
/'

-(-c

-'~

H0
e
-

-c /
"

C>

.....

01-1
II

\J(I.().

M.:t.lo(\i.

SIll..

\\

I-W ,
,

-c -

CII

'OH o.r...t. \.
prepll-(Clh,.

Cl.ddl1.·lolV..

Es. n.Q 8 .IS:

SUivi k_

r(l'l\Uk cL.. S~(V~(1l.. ch.u.' o..ldutU

b)
A-METILtIUOEYWOLo

~lA. a.k~ J.o..

c) 3-EY\NOLO
tI-I~(HlI-{:. (

u_.V..

t,Lo..~LV(\Ql(.QL

%li.wlt. pJ5 ewrt

CH~

0..) l-BuTANOLO

d) I-METlL-l-PHJTANOLO

CH~LHl C~ = CJ~l.
Cl-t3CH :: (I-H.I-{ s

CH (H1(H~

C~ LHlCl-l1(Jt = 0-1 CH3

CHs C =: CJ.l CH1. (I-IJ

(~~
I

CHz. == C
CI-I~ I

CHlLH1(H~

C)"{) (1-1 LH = U-lc..~~

e)

O(LoP£NrANOI..O

.) d+ +
I Br

a-

~rl

---')

ue

t,

w.lo pef\.klU.OH
~
10@

O~
~

011

H/ '~

Es

,1\,0

g, ~3;

SLCwi

u. ~u(l_'tiOM.
~gr
wlott.
K2(ftO~

per

It
~

i-tQ-l\OM

ch.u.'.Ii ()I
01\.

SUTANOW LOI\ i waOCf\.-tL

+ ,A
1-

~f\,t.

0-.) W~(.Hl.LH1('Hl-0I1

NQ.(NIl.~I\'w)

CH3CH1.LH1.LH1. -0 NI1
BUTILAfO SODIO

1f-tl.

b)

LH3 (j·1t (J.{1. CI-l1. - 01-1. -OH

)/
'>

pef(.\~ e
11

Q.lwl

P(iMO-f,O,

9u.liUL.

t.A.

VlJO~

{I\.Le 1.

CO('t\t

Ul.+uu·twJo

It.

10\

c) CH3lH1..lH\.lH1.

f.lJOt, ,U)..to~
SO(£1.

CH3 (.H1. CH1. C - 0 H

A.lIDO BlJTANOIW

')

tH-sLH1.C.H1.LH1-(£.
A-Qollo BUTANO
I~'

+ SOl.

--)

tH3 WI. LH1. C. -1-1

BUTANALE

Es.n.o g.3~:
t

s<.(\lIi

ltUjvo..:iloM per lR.. tW..-tio~ Nt fYle.l-u.lliLO O-Na.+

I

d.tl

2-BUTANOLo

(.0(\

I ~l)(.JL

~!\.t:.

OH Ov) tH3 LHt CH CH 3

~ (H~ CH l (Jt CHS + Z-BU,ILATO Dl SO()IO

T Hz.

b)

OH
I

tH3LHl LH LH3

~~SO'"
\ALor{.

(HI
)

011
I

H
::>

" /C = C /"Br I

H
hu.{\~ Z.- &!TENt (Hs
1-

c) CHJ (111C.H eN l

HBr c.olott

(1-{1WLCHLH?
Z-CIl0'40&JfANO

1-1-1.0

furANONE

0-130-1,. CH CH$
L-u'Oa..OSuTANO

.j..

S0'L

l'
llil\~cL.o

Es.1\. 8.36
0

Q\iQ.[' e il rMlc.o.nA.~N\O
_8

p,ii rro bo.1Ih.!~llvi La. foflYlvlcL eli. ~6-uliu((L per

~H~
t~

tto..-\l4.o foCfYlr..lo
\H~

c:LuCUA"ti.

Lc.. ~-liOOlL.

~H~ ~~

Q.l3lI1LC-O-H

+ ~ ICel -')
-

CH3UhC(O',
(H~

)t
H
~

~H~ ~e

-~

013L~t(f)
I

+1(£1 --')
-

CH~lHIC-[e1
I -

of"

H10

CH3

(~3

(H3

A,1-0fMfTll- A - PR.oPANOlo

E~

.1\.0

g. ~t; lolYlph.k
-I-

~UQtIOl\i

cklh. Je.8~ili t{O.{IOM.

10\

~) 01~(HI LH2 OH

Hz Cr O~

--'>

(H~ (~1 ( -01-1

II

b)CH~01LHLLHL0I1 +

(H~ I

(J.l~

so«,

-:>

O-l3U101l.LH1-Le.

C)
~

+ Hce -)
~

e)

OO~
+
t

~LCrOt., -')

0°'
CH ~-(-0- -GIl~ I I-METos~t
CH~
-l-MfTiLPfloPAfIlO

0-13 _ I

~ - O-~

L-METtlPnOPENE ( IW8lJfI LENt)

MtTANOt,o

(ET(fU: -kn - BurILMET\ULO)

CH~
I

CH5-~-CHg
OLH~

J..I+

E~,n.°g.39:

Most(Q.
It'\.

LOI'I\t tfll.~~(I't\Q..t€-:

Q..) l \ A - PtoPANOLO CHSCH1CH1-OH

l-PRoPANOLo

if\.

dw. ~lll-dA.
CHs(H=(~1..

H~W"'LOnl. ~~

d) il

Pf-OP€Nf

\1'. Pfl..oPANDNf.

(Al£TONt)

111. clu.L

~ta.dA..

OH
CH3 LH Li~s
I

il

U[Lot~ANOLO

rui

~I){jl-l IJ)l'I\po~ti.

b)
,

CIWJ(;SANO
\.{lW~WIIL,
'>

~'

~1

-'>

Pd

E5.1\,o K. 4~:
a.,) PltoPANALE

~'I(\te~:HQ

'I

~t31J{1\.t. W(VIr').st.
10'
(H~(Hz

Q.

p.ut:.tt. J.o.ll' ;!-PO_OPANOLO

Pee

b)

AtiDO PII.OPANOIW

c.-I-!

II

C) PR.oPfNE

d)

1-PQ.OPANOlO

0l3W1LHl -~

n .;{
o

-lLOG..o P(lD PAND

A ) CH3 LHtCH1-OH

I-JLe
WOr(
I

~n((\

) (Hs Ll-ll £.HI

-ce

~) P~OPANDNG

~.) -1,1- P(LoPANDIOlt) CH3 (H =- Lf-t 1. CH3 (~ :: LHl.

,
--)

050~ Hz-oJ.
KMr\O~

OH OH

OH -)

lH3lH

I,

(Hz.

I-\(OOO~
l-{-LO

?H
) (}I3(H U-{z

Ol-l

0...) A-METlLC.ILLOt;)ENE

b)

kMHILLllLOESANOLO

c.) l-MfflWLlOESAf.JONE

t)

(1)- "j-MHll- --J,l- W.lOESANbiOLO

~~H
~

tS.r\°

g, ~4:

A-IDQOSSIMfnl..-A-MtTllqlLOf'fNTANO

lYIo~hu. LOw tra..~~rt'i\Urt

- A-MmLClcLOPfNTANO

n.tL ro;tl1t.ciA. (,OMpOJtL.

0.) A -(WfLOMETIL

--~
h)
,.J- fO((.MIL - A-METl LClLloPENTANO

v)

4(100

II-MITIl.W.t.OPENTANOIW

A-CAf.Bo5~( - A -METlLL!LLOPENTANO)

---'>

HlO I Q.ldDi\x'-

4 ~r('l\vlt di (I~OI\.O.I\\Q. O\R._\om.u\(,Q plV llt~~o eLd;hOl\o.lI-ru.[h)rt dill' uLeb:l.t.- : l' (VI- AlHllFENATO [lJlUL ~ phi ~JQ.h,lt. tiLl ft NA ro .

C-H
IQle • CICloE-SANOLO
I

MHANOLO

Ft-NOLO

ACiDO ALETIW

H
1-1

t.I ~;r (-01 _

e
SoMl

il 101
I

CI(_(.Ot~AN.ATO e
10rv0

bQ.~ Mollo ~("L:. ~n.ki

QU.dA.
MO

rjtevorlo t..O.it(..O.- f-( t~li-o lMiufuvo pili (ofh clt\ METANAro ~«lJ: II W(({'pOMJ~u. olwl

_e

~v!-i.
'-

e «(,Of\_cktio

Ito MOL.:. perl\-[ puo cklow.lA.no rf ~ (.Q.r~LO... W l.<{'porkM II ~lAo dU.. U)..r\?o~ oLd ftNATO

LH3 -c = 0/

l ALETArO (: Ut\A.. bo.K l'II,olto

n~vQ
iU

'\

Z.
~

OSkge.v.
U\,G.

~to_bil£_

__

9uA.MU' t' ALEfATD

..-..:>

bQ1.{ plu d.J,olt. old ftNATO . cu.i.oLo

L\ ALIDa

A(.€TI La t

IA

P"I ~I-Q U

dJ.1 FtNo Co .

Ao

4 rrrnvG..

di

(iSol\,QtHQ.

O\R..Sofl\t(,(..Q..

..

elilirol\..o1:lrultolt. G.u;.tu:Ll ;1 m-FoIl.MILFfNATO e. ptrcio l ' IY\ - fo~\llJtNDL.O l pi0 ou.cto ckl t1:NDLO.

It. ~(VPP::>

~(1YI'1l

ilL ~OK~jO(u'

MffA s~bil.lH(l_

Ko(!Ytuk ck~ fEN~TO pOiL~ e

()I\..Q.

hax pi\! .l~blu.

Oil. trvppo (piii cJ..JlOk.) ckl ftNATO

rfMvlt.

di

(IWI\AlJ\'l:Q. O\Lso~(i(.(L

+ l'~ffeU.o

'I~O

eLdi(01\.. o.:lh·d\·ore.. <itt tc1rwO(owUlt..

(.(j.(I(..Q..

11 sruppo +{,~luo(Or'l\.d.,LLL 'II\. poUt·,or\J. PMA ~6.biLu.%. B'lOLiA.!UMO Lo... Moltu)~ pt'Ic\u.- 9ull-l\.d,o tc, ~t.:~ e. 5,v[ lA(b~tJ.o tAA.i_ ~OI\.O ~ ~I 3 f~o(i ~\I.LlIti lc.. o...ll~ F effttko ·,nAlvtUvv. auA.r.A.i. qUJ»f<l.- e VML bQ.¥C Q.nw(Q.. plv ~1-o.~dL (piv cltbola.) o\t\ M- fOfZJVIlLfENATD pWA.O n p-WIH.wQ,oM81LltNOl.,O C piv aud.o cU.1 IY\- fOP-MILFENolO.
I I

ALETOFENONc

L - F€Nil-l_G~ -

BUTANOLO

b)

PIlOPIOfENONE

O~M~-8 0
II

G,\

f~'

M~Br
-& ~30(fJ
';)

O~
i

C-(HlLH~

(I-Ir C-U'Mf13

(H~- C- (J.jtlH3

-':>

(-FEN I!. - H>UTANOW

(H~- C-(111(_H~

c.)

L-F~NJL-1-8lJTANOlO

o
011

01-1
t -')

CH5 (Hz. (H1 -

(_ - (j..i $

(H~
l-Mff(L- L - PENTANOI,O
I~
0

-)

CH3 - ( - LH3
I

-)

1-150111

O~
I

lH3 - ~ - (1./3
(H1tHlLl-')

CHtU11.(H~

Z-MtTll- 2- PENTANO(,o

l-MfTlL-l-PfNTANOLO

[S. Mostm.
0..)

i ffOclofu OULlWt tkLl' ol.clviloM.- Atl ~Muf..o III

MEnLMAqAic.sIO

t4 ~lttl\.ii

U)l'f\f'O$t: '

~Ol
CILLOPfNTANDNt

(~3- M~Br

-~
(j)

~[M~J$
(,1-13
I

b)

0v
/0'

to)

"C

[M%ErJ 101 +
(H3 -

~I

M~Br

-)

()C~
I
IOrOvl~
f

CH~

6fNl-OFfIJON€
/0\

t) (H3

LHt U11 (

"

Br!

(,I-\t LtI)

+ LHs -

M% Br

-)

CH3(H1.LH1.- C ~

~-f~ANONt

013

LH1(H 3

E$.

usa.

UI\4.

tto.-'l:iol\L J.;_

~r'I~

l\.O.(d

~r pttpa..ro.tt

'I

~ut(\t:
b)

(}.kol,

0.) Z-METlL-l-Pe.oPANOLo

;l-NlfTllil(LO~~ANOLO

t) 3-MtTll- 3-PENTANOi;J

d) 1- FENll-l-SUTANoto

~-MHIL-A-PfNTANOLO

~I-I~

CH3 OU,H3 ~

Le1

CH3 f -(H~ fOH ~ C~ - [:= l~

U

~~~

KOI-l

~~~

I-IBr
KOO( >

(,U3

LH3 W (H~