Page 1

mild oxidation

0.0 .

n.iii.iii.in
h
Alkaline iodine h

in

☒ ¥: '
on

Ha

Compiled by Dr. Teh Swe Jyan

Page 2

Pent } . rene - 2 - one

red 1
orange ppt

CAN 80
✓ Ctu

✓ delolonvise bromine water 11h00 1600cm -

' '
I alkene

absorption at 1100cm CIO

-
-
l is

-
absorption at 2h00 - 3000cm ' '
is Orn : carboxylic acid

-
no vis trans so is chiral

¥0

Compiled by Dr. Teh Swe Jyan

 Page 3

:
u ; N In

✗✗

trigonal planar

•
• •
•

Compiled by Dr. Teh Swe Jyan

Page 4

u forward and backward reaction at same ✓ate

✓
less products formed

equilibrium shifts left 1 fewer molecules)

gas
✓

Inanna .mn ,

Catalyst increases the number of particles to have

energy avtivation
>
energy
✓

u more frequent sncessfnll Wlission

Compiled by Dr. Teh Swe Jyan

 Page 5

nucleophilic addition

8- Ht
[ I
On
'
St

4 in
c

f i' in }
'

mu
/ , ma
CN
• .
CN

Compiled by Dr. Teh Swe Jyan

Page 6

n n
l l
? Y
C -
bul
- L -
h
n -

'
'
h h n
E ,
N

Mll

concentrated NaOh and ethanol

¥ '

n
:
'

Compiled by Dr. Teh Swe Jyan

 Page 7

Ch } Cnvlnv

fy fu
I
→ n - o - on

y
↳ .

n 0

÷: : :
vi. i. u - u -
n

eteitwpniliu addition

5 has methyl group next to mon 1 has in } In on

Compiled by Dr. Teh Swe Jyan

Page 8

✓ Positive inductive effort of more aknl groups

Suon
dairy carbocation is more stable
-

on

* ^^
no

LU} LUO curling t 107 → In } v0 tlnv M3 4 NVO

Compiled by Dr. Teh Swe Jyan

 Page 9

methyl pentanoate
✓

Compiled by Dr. Teh Swe Jyan

Page 10

Compiled by Dr. Teh Swe Jyan

 Page 11

uvvay

Initiation

nut

Propagation

"

elimination

Compiled by Dr. Teh Swe Jyan

Page 12

not i acidified , wnlentrated KNIN 04

muon bxene would have absorption at 1h00 - 1680cm "

because of

CIC bond

Mcloud✗ ene would have absorption at 3000 ✓

31001m -1
because

of urn bond

adipiu avid would have absorption at 1h00 -

3000 im 't

because of won bond

Compiled by Dr. Teh Swe Jyan

 Page 13

Ca t 2mn10 } → Ca Into 3) r t Mr

✓
lastly does not react with ur soy

✓ lastly prevents the ✓ eantion of ur soul and Ca

"

( /
¥
✗
*¥
II ×
✗✗

XX -

① ①
0 0

o=É - I :O

Compiled by Dr. Teh Swe Jyan

Page 14

b) bath

Clut Wh ' → CI CIO t Nro

'
t
-

-
I +5

gains and rose neutrons

carbon dioxide , water

Compiled by Dr. Teh Swe Jyan

 Page 15

✓ MON

✓ MAUN

- Kvlvv 07
-
nv soy
✓
heat under ✓ efwx

hydrolysis

reducing agent

C attained to 4 diff functional groups .

Compiled by Dr. Teh Swe Jyan

Page 16

00 O o

effervescence no reaction no reaction

orange ppt orange ppt

no reaction turns green

2Mt → Chihiro

Compiled by Dr. Teh Swe Jyan

 Page 17

Geometric

OHC Chick }

\ I
C =L

h
'

"/
i . .
"
°
.

absorption at 2200 rib '00 om

' '
because of CEN bond .

absorption at 3200 ✓ 3690cm -1 because of Orn bond

Compiled by Dr. Teh Swe Jyan

Page 18

aldunn.de

It f-
Br
-

[
°'

reduction

i /
Absorption at 1610 -
1740 im
'
because of V40 bond

Compiled by Dr. Teh Swe Jyan

 Page 19

NaOh

aqueous

ethanolIv

concentrated Nv soy and heat under reflux

ri
'
or

ethyl Pwpanoate

Compiled by Dr. Teh Swe Jyan

Page 20

00 O

CH } 1h20m IN lunch } CU } cnn.CM ION ) LUIOUILUZLU }

Ueomerlriiat optical

Compiled by Dr. Teh Swe Jyan

 Page 21

:
dehydration

acidified potassium dichromate I V11

✓
distillation

✓ to avoid further oxidation

wnientvated Urso 41 AND }

Na Bv with wnientvhted Mrs04

Compiled by Dr. Teh Swe Jyan

Page 22

CU } cuz yt
\
8-1 8
J:
-

n - c -

" I

;) CN

on on
l t

C ' ' ' ' ON " 't 6

µg '
/
An Ab Ch } Mv
Cn } Chu n

- It has a chiral carbon

- because the carbonyl / molecule is planar

Compiled by Dr. Teh Swe Jyan

 Page 23

Compiled by Dr. Teh Swe Jyan

Page 24

I 7.

Compiled by Dr. Teh Swe Jyan

 Page 25

"
,

4. in }

3- hydroxy but an v2 - one

acidified Kutv v01 and heat under reflux

Absortion of peak at 1670 ✓ 1140 um - l because of 040

Absorption of peak at 3100 /

36h01m -1
because of Orn

absorption of peak af 18h0 ✓ 3100cm -1 because of low

Compiled by Dr. Teh Swe Jyan

Page 26

In } CO LUI Chu

-
no chiral Larison

✓
so mirror images super imposable

✓
Chiral C

COCU } M3 GO b
l
l

C ' ' I G "

111 N y
Br
BF A
n¥ ,
143

Compiled by Dr. Teh Swe Jyan

 Page 27

molecules with same molecular formula but different

structural formulae

overlap of s with two p orbitals

overlap of Smith 3 p orbitals

1200

109.50

h
is it
n -
o -
b - bei - n
'

Compiled by Dr. Teh Swe Jyan

Page 28

-
electrophilic addition

-
brown bromine water turns colourless

is in is
L L L -
n
no -
- -

'
n tsrhr

carbon dioxide

i is
b b -
h
"C
- -

propanol ' '

h f y
pwpanone

CUT }

-
molecules with same structural and molecular formula

✓ has chiral b and non ✓

superimposable images

Compiled by Dr. Teh Swe Jyan

 Page 29

I
+
is on

me - CHU →
""
" " → movie -
n

÷:)
, IN
CN

Compiled by Dr. Teh Swe Jyan

Page 30

Unbranched A has a larger surface area , hence more contact points

between molecules .
Id IN
- force are Hatin than unbranched A

molecules , more energy required to break the intermolecular

forces of attraction
✓
,

cub CU Cn th }
✓

There is no rotation of C :b double bond . Each lot b :b is

bonded with one hydrogen atom and one methyl group .

Compiled by Dr. Teh Swe Jyan

 Page 31

n
"
m h h h h
GIG I 1 1 I
" → nothin → vi. Cru - n

" I ④
'm
'
8+8 .

mr E :B; ar
Br - Bv
↳

repel
high neutron density in
rmeneiirtwns away from the
nearest MV
✓

on ? UM }
this
"°
mud - Ch } no -
c - i - n
n , j - u
' '
°"
In }
'
n un } ✓ In , ✓
✓

V14 V8 Out Marlo } Nuo

→ V04 My Ov Nat t
long

Compiled by Dr. Teh Swe Jyan

Page 32

Tri iodo methane

✓

Cnb th v th 3 Win } ( CU } Mv Mb Coby 3)

1 1h
cunts In Mb )
Of

A carbon atom with different functional groups

attached ✓

Compiled by Dr. Teh Swe Jyan

 Page 33

[ Ib bond and 0 -
n bond
✓

CYL bond and I -

n bondy

trtnanoiu avid
✓
meth
Methyl anointing

Compiled by Dr. Teh Swe Jyan

Page 34
u.i.i.i.in '
' '
O n n n

✗ viodometnane

Butanone

i :
n-i.io?u-iIiii.ncm-c-i-n in }

o o

reduction

Nanny

Compiled by Dr. Teh Swe Jyan

 Page 35

nt
i :L
'

f St 0h )
ft /

a
y , c-
youuu

:
( in

optical

- ✗ has a chiral centre

u Whr super imposable mirror images

Compiled by Dr. Teh Swe Jyan

Page 36

C n N 0

9.40 12.0 27 .
}
91 } .

0.857 1.106
4. 275 9.40

10.968 I 1.995
4. 994

(121911-1111)-114416121 / ni 117

nil

Chun NOV

EFM "
RFM

Compiled by Dr. Teh Swe Jyan

 Page 37

3 -
chloro pro v1
-
ene

109.5

1200

CI on on ,

a.
i - i - i -
n
.

huh
'

0 o n .
.

↳ MY CI Or

oxidation

Compiled by Dr. Teh Swe Jyan

Page 38

O O O O

Ai B

✓ silver mirror
B
-
blank / grey ppf

'
yellow ppf
Ai b

LID -
effwversenue

Compiled by Dr. Teh Swe Jyan

 Page 39

- electron pair donor

:C N '
/ cyanide ion

ii. on

optical

bn } N} b
I I
C 1111
On
°
\
pill
-
y
At
y A n
Nb
CN

uh } LUIOUI Won

Compiled by Dr. Teh Swe Jyan

Page 40

Clio and •
Ch 3

'

01 -

and tens

oxidation

condensation

reduction

addition

Compiled by Dr. Teh Swe Jyan

 Page 41

o o

o o

o o

aqueous Narn
substitution

ethanol:b NaOh elimination

etnanoliu Haunt substitution

dilute nvsort hydrolysis

u acidified KvWvO1
oxidation
✓
distill

✓ audited KvWv07
oxidation

Compiled by Dr. Teh Swe Jyan

Page 42

ft f-

on
-
-

molecules with same mountain formula but diff

structural formula

Positional

functional

skeletal / chain

Snl

Compiled by Dr. Teh Swe Jyan

 Page 43

molecules with same mutant or and strnvtnval formula ,

but diff arrangement of atoms in spare

✓ no chiral b

-
one b of double bond has identical groups In )

2- into ✓0 butane

I / uh WW butane
01

c- I - u - u

optical

Chu LU } In } IN }

k "" u
I
¥ huh
/ "
'

} UC Nz n }
01 ,

Compiled by Dr. Teh Swe Jyan

Page 44

0 I o

it
y O
l
l

n -
c - c -
y
l t
h CEN

dehydration

n , c- c
in
-
n + lot → n } or
?
n
- won + uvo
,

Coon

auiclrtied potassium KVCV v07

Compiled by Dr. Teh Swe Jyan

 Page 45

nnolevinle that we won ✓

Super imposable mirror
images

µ , '

n
:*
'

Compiled by Dr. Teh Swe Jyan

Page 46

✓ 1 experiences greater positive inductive dftevt due to move

911141 groups

u
whim stabilise> 1 reduces the charge on the intermediate

↳
f
g,

g .
i : Br -

nucleophilic substitution

Compiled by Dr. Teh Swe Jyan

 Page 47

61h1 -7 In } 140 Helmont UVO

252 Zpb

number of shells increases

Compiled by Dr. Teh Swe Jyan

Page 48

Ahr :[ 31-61.81+1,692.911 (31-204.6)+1-1820111

-

i ✓ 878 }
. -
l - 199.9 )

'
v82.4 V1 MOI
'
I

✓ 82.4

Compiled by Dr. Teh Swe Jyan

 Page 49

an collision between particles are Masti -

no force of attraction between particles

particles have neg Weniblevolnmb

✓
Particles are close

-
repulsion force beware sinnifruanf

Compiled by Dr. Teh Swe Jyan

Page 50

lull } t
'
l v Ov -7 V0 v1 v th Ll

s ?

Absorption of peak at 1670 -11401m

' '
Deva use of 040 bond

Absorption of peak at 18h 0 -

3100 because of b- U bond

Compiled by Dr. Teh Swe Jyan

 Page 51

✓ effervescence
✓ ✓ LOON

✓ no visible reaction
× ,

✓ orange to green ✓ alcohol

: u - C
1
- on

CIN

Compiled by Dr. Teh Swe Jyan

Page 52

dilute Musou

free radical substitution

Uv ray

ft

f. ¥ .

reducing agent

cry v03 t 2147 -7 Cuh 403

Compiled by Dr. Teh Swe Jyan

 Page 53

absorption of peak at 2h00 ✓

3000 im
-
I because of Kwon

range of 3200 ✓
3640hm ' '
due to Ro -
n

Compiled by Dr. Teh Swe Jyan

Page 54 443

unfit
2- 2 .
dimethyl propanol

0
0
0

spv

:
acidified Kvcvvo 1 and heat under reflux

Compiled by Dr. Teh Swe Jyan

 Page 55

u A has hydrogen bonding

u
B only has pd pot tones
-

is than
-
n -
bonding stronger pd pd
-

11h31 } bvnotrfn? → 11h37 } on von

nasty

Compiled by Dr. Teh Swe Jyan

Page 56

orange Ppf
aldehyde
orange ppf

aldehyde

0 with 4 diff functional attached

groups

cnv
4h0

n
-
' ' I
§ \
Ling yn ↳ ✓
b 111th
☒
on }
Usb

Compiled by Dr. Teh Swe Jyan

 Page 57

Compiled by Dr. Teh Swe Jyan

Page 58

00

It f-

: on

Nbb
"
1
C - I un
1430 -

1
t
Chron
no

Compiled by Dr. Teh Swe Jyan

 Page 59

11h -312 In un 10h1 Inv on

optical

09 Mirror 1- 3107 →
09h80 } + VU v0

✓
And bromine water

✓ brown to colourless

in } Y

l : I
'

b.

In } turn

Compiled by Dr. Teh Swe Jyan

Page 60

&

3- methyl - but an - I -
01

heterogeneous

Compiled by Dr. Teh Swe Jyan

 Page 61

Compiled by Dr. Teh Swe Jyan

Page 62

Compiled by Dr. Teh Swe Jyan

 Page 63

Compiled by Dr. Teh Swe Jyan

Page 64

Compiled by Dr. Teh Swe Jyan

 Page 65

Compiled by Dr. Teh Swe Jyan