•

( HEM l OOZ.A ~ 2oz?i Sf Ec. HA ND IN I UTORIAL.2.

N!tME ~ IS HE:PHlu Twi\U\
I
___
ST 2'31:,t; 822
,___ - - - - - - - ·- - - - - -- -
I - - - - - - - - - - - - - - -- - -- - - - -
,1. n- pen-tane'! CH z, -CHz. -C.H-z -CHz.-CH
-\ Mol@cu lat lo n ·- -e,
=, _.:.._~<-...::::.!___!__:L-_ _ _ __ __ _ _ _ ___:___ _ __

---
I .
lH aCl-lz{tb Cl:f2..k..!Ls
- e2
~ ;,- [ CH?>CHzCH2 CH 2_~ ] +
- ·--;---- - - -- -
_ __ I. : ., 5~ 011 ) t 12 ( 1.001!)-.: l~S I ·--=--- - -- - - - -- - - -
! 7:1.l5\ - 0.,055 -= 7~.09'"""'b-'~- l- 2.____ _ __ _ __ _ _ _ _ __ _ _ _ __

_ --__-_- l-i_._ l '\ /..::ez _ Fo1

4
molecular io~ !>
7
' I~---- - ~ _ : _ - - - - - ~ - -- - - - -
- I er\ncipqi rrqqmenl-- ion I . ~
__ l_-_[ c1hCH2.( ijz._C_Hz.C l1~1-+ - 7 (CHaC H2. CH2 ~ i+- +_ Ol3
_ _ _!mfz. =Ta -

___ I -
- - _I_ er1nci pcil
___ I [
-=--
1s -=- f, ':l-

f l a9men} io: z. .~
CH3 CHz. Cl-l2 ( H2, CH~-:r1 ~ -[
--=--- -- - - - -- -- - -

z. CH,J .\- .\-- Ct13C.lh

C_H_,;,_C_H_
Im/z. = ·1 2-23 = 4 3 - -.::- -=---=-"'--- -=----~-=---- - - - - - - - - - -

I
r inci e.l - ,a men~ ,·an 3

__ J L Cc H? ( +-lz. CHz.C H2.C/-/31 + CH3lHz._J_t-_ +__:;,c..:..:

+l.L 3-=C..:...H.:::.
z.C_ H
~z_ _ _ _ _ _ _ __ _
___:i, [

__·_Imlz -:; 12- 43::: 2. "'!._ _ _ __ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ __

I
. · 1I
I pnnc1r1. F'""~men f '
IOn if
;7
4
[CH3 CH1. CH2. CHi.iJi~l-t - 7 [cH 3 1 + C.t-l3C/-1i:.CHz. Ul z.
l'YI /-z. -= 71- 51 =- 15_ __ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ __
\

- - ~b.. 5 C, a.tom s ,n n - f-eh{qne •

rs.
I'-_ _a_nj whe1e in 0-r-ttl-c
~ rn:.:::&:..-_ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ __ __

-I •( f\{\ + !.!.
I) _+ -+F~
' !::..k_'.:.'.in_ :_:_
n -~ p:..::en~-lo::.:;n.:.. VII 1
e ---: ..:.:,l/_ be,
--=---=S:_
·· 5_ °_,_,/o:,__:of-f___:_;_
rh:..::_
e __:_;:
f-e..:,: t """"4
i~µ~c:::. 0F:___!J+l-e
~ __!M
U~
c........jr p!k.~ . - - -

1
e-
- -.. - - 1- -
 -- -- - -- -
L
- - - -
----- ---- -----
. - - -~ r--c+tum It 4-he ~fanol. i± is , ~1_m_m_et_tiq_/_ v_~_u_lt_in9 in LJi~fe1en-l _g~f c~ern 1ra//y _
. I.Don- eelui'< len1 en bon a-loms as s aw n in e s\r u,tu re I drew s boue. H.f~,e _)Jee_
,_ _ /s ,~hatms Ghows 4- c~ Lmes.
I
I._
I - - - - 1 . _ __

_ _ - ~~ct, um z: 3- hepeno I • 1 he moJ! '-cJL s how; 1 4it+ seis .£f ch,m "• II g non· c9ti'" lenl
_ -._Ll!!f bo n
____,1 / q{o m, qs £bow n a b,ue . Hen" Iii<, s ~ d t cm _ _;S~ho~w:'.. .s:::__·L-.:
7d~,.::_,
Gt:::..1:.·.:.:..:
"c:..::~_ L_:_n_e.=_
1
5 _:_· _ __

____ , - - - - - - - -- - -H- H- 1-f- H- - - - - - - - - - - - - - - - - -

_ _Jl_a<lL_[IJ
--Mn c 1- oj_, .H_- f -=-f oH

==--c ___ -- 1

_.___, _ _ d rJ_~ ton- 2- i?_I: _

H H H H,_.___ _ _ _ _ _ _ _ _ _ _ _ _ _ _ __

- H H__o_lL +ll- - - - - - ~ - - - - - - - -
I
ti - t - =-
I i
( -.. .f:::c.-::f;: . .---'
- --'H-_____ - - - - - - - - - - --

/ ~- tl H _!_H. L __ _ _ _ - - - - - - - - - - - - -
!

---1L_ ,11·u <- m, HiI P'~/""0- 1-0I :.

--~-- I - ll )
=l-H-
;...jL~ I
C' .d C~ C,
I~-~
-O:!JH
~ -------------
_ _ _ ,._ - - - - - - - - - -7 HtT="
t- C- H
.~ H~
. _ _ _ _ _ _ _ _ _ _ _ _ _ _ __

- J-IL- - - - - -H'- - - - - - -- - ------

- --+-- - - - - - - - - - - - - -,-
[
I U~
I

i iv) 1- me+hyIl"'f"ll-2-ol : H- tft I

---,'---------- -n-t~
 \3LLlan- 1-o I

Ii -
1 1
1
C- c.- c.-c-o-H
I I I 1 5
After addi ion \-\ t-l H 1-l
of D20 2 3 4

4.3 i4-2 m 4.1 4. :)_

1

TM5

4.2 4.0 3.8 3.6 3.4 3.2

3.0 2.8 2.6 2.4 1~ippm)2.o 1.8 1.6 . 1.4 1.2 1.0 0.8 0.6 0.4 0.2 0.0 -0.2

J-me-1:h~ l'DpQn-2-0 I r After addition

b of D20
1-j 01-\ H
I I I
a. H- C - (_ - C - H G\
l I I
2.6 2.5 2.4 2.3
tlH-C-HH fl ( ppm)
I
H
ct

--,--.-,~~--,---,-..,.....~~-,--~,----.--~r---;- ' '

4.0 3.9 3.8 3.7 3.6 3.5 3.4 3.3 3.2 3.1 3.0 2.9 2.8 2.7 ~.6 2..5 2.4 2.3 2.2. 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4 1.3 1.2 1.1 1.0 0.9 0.8 0.7 0.6 0.5 0.4 0.3 0.2 0.1 0.0
fl ( ppm)

.;1-me-1-hy! propci n-1-0!

(l
~1H b 11-J c.
al
I ll
H-C - C. - L -Q-H .
l l I
H
H H-C-H
l
QJ H
3.45

TM.:S

' ' '

.6 3.7 3.6 3:5 J.4 J.) 3.2 J.1 J.0 2.9 2.6 2.7 2.6 2.5 2.4 2,3 2...2 2.1 2.0 }i\p~~) 1.7 1.6 1.5 1.4 1.3 1.2 1.1 1.0 0.9 0.8 0.7 0.6 0.5 0.4 0.3 0.2 0.1 0.0 -0.l

(3 X 4 = 12)
[16 marks]
 - - - - -- -
-- ----- -- ---
-
' IR -
- -!----- 6fla'llt1Ui'h , _ _ _ _ _ _ _ __
- -- -
--- -·- -- - - - - -- - - ---- - --
_:_~ ~~Jl:!.L C.-==- O s-l r'1 +ch a. t 1100 cf'Yl- / -- - -
! - - --
- ,!- ~ ~~~ - ------------
C.-o strekh q-! 11~0 cm-/

I, H NMR
I Siq nq/ I SJqr,q I 2 S1~1MI -:3 Sic\Ylq I
I 1,/
S ~t'IC\I s
'.deir1 S~l~t 7023 1. IS 2. 'is s
Raho I I 2
2 -b&

'2.
7 . 0b

3
-
Mvllj~ cl t 4: 5

-o Noot Hi:t1
cuJ.a l
-
art! c.,
J I 2. 2. 0
A~~w,~
. I
L.::7-
V.f -@ -@ @ C,-(-H<

I
\ 13c. NM~ S19nc./ , s~ 11ti l 2 Si t/ rict l :3 6 ,·•1 11 ... l 4
lc~em &liiFt '2. 0''1-.S /ttl. 2 It'd -1 /,zg_-b
\ A~ iqnmuti C.=-D - l- ·-CH- -C+I-

IIsc. N,,n,_ S,qnq/s I Sic/ nc,/ (,

I S \qvicA 1
I

S,"lno.l
J
I
ff~JI Ckf)\ shi~t I i 1..\6 ,Cf j 4 5.3 30. I '2. '1. 1
I Assl9r,1utt I -(.,.H- (
I
- Ct/1- )
I
-UI, - I - CHz-

I
I
I
!_ _ _ ___________________________
1 -1
I

r~-__
- - ' -- - - - - -- - - - ~ - - - - -
I_ _ __ _ _ __ _ _ _ _ _ _ _ _ _ _ __

I i