Week 2- Lecture 1 10.10.

22-a
*
H CH }
1 /

H - C- c- H
1 1

CH3 H
a
H
H H
CI c
* c
H -1
C C- H
H
H
µ

HJC
=
#
C-
H
Br
-

B"r |
H

!
*
ufk! " '
H
/
C
NH2
A!t
[
032
-

|
:O :
:ö :

"
a rezonans Structure
/
.

÷ .
µ; ÷

:& :

"
0 •
Ö:
•
80
 * :Ö
-

:-O : 0

d+ H
H
+
CH2
H H
-

Rezonans double bound !s

longer than H

double bond
a
regular .

* 08 part!al negat!ve

④ part!al pos!t!ve
8-

* 4
% N
}
H-c-nf-FE.!n .

* ←

!t
Ç Ü=N=N
:
A-
-

!t

because N cannot form

5 bands ?
 allahım sabır

Funct!onal Groups
ver
:>

1
alkyl →
alkanessp}
2

alkenylakenes p23alkynes p4Aryl-phen"l-a.ro mat!c compound

5 Alcohol
<
ı OH

pr!mary Secondary tert!ory

alcohol alcohol alcohol

!t ÇH} ÇH }
C- OH C.
CHG -

/ \ HŞ
-
C- OH

A- +5 ↓ OH İH }

1 H NOH attached to the center carbon atom

21T
OH
0 OH
* * +
µ
µ

!sopropanal
*
0
ether ( soul)

*
|-O -5 another ether

* .

SH th!ol
* s th!ol ether
 6 Am!n
summar!zad!n
# Table 1.6
* N H 1° am!ml
f-
-

µ
-

İt
*
↑
H
3° am!n /
,

* 2° am!n
µ

⑦ Carbon
ye
* * 4 ÛH
ZCS carbonyl A- c- aldehyde
¥
* % T/ Whenyoudr!nkmethanol ;
"tturns "nto
tox"c
formaldehydeoformaldehy.de
wh"ch "s very .

(mumyalanmadan kullanılır)
µ

IThecuneformethanol!sethanol.to
Benzaldehyeks 11 Ester
Q
-
◦

•
µ
_
CH]
-
H 0

12 Am!de %,
9 Ketone
F- 1 \
û İ \
"
,
-
C-
H /
C- CH3 NH2 \
µ
CH} \ r
_

13 A-
lkyl hal!delhalloak.am)
10 Carboxyl!c Ac!d
o -

& -

× ×: F. G!b! / I

at 14 N!tr!k [ Hz -

CEN
%
More Complex ones ( we !dent!f!ed groups "n class)

Pacl!taxel used for breast cancer

I When OH connected to
aryl group , ITIS PHENOL

AZT → used for AIDS

Week 2- Lectures

Chapter 2

AIkdnos-everycatom!sspsc.!n
Hantz General Formula

lcarbonalkanelmet.name CH4

2 "
ethane CHS -
CH}

3 ✗
propane.CI/-z-CHzcH3
4 "
buthaneCH3CHzctb.CH}

5 "
/ postane

6 "
hexane

7 "
heptane
8
•

"
Octane

9 ✗
nonane

10 " desene

IUPAC
 Nam!ng Alkanes

4-
E- E-
" c-

H
{ "
¥ Ü
{ 2 3
1- propyl butyl
methyl ethyl
→
2- propyl ~

ISOPROPYL İsobutyl

tert-butylltalloalkanesF-flus.ro
B!r Bromo
-

G- ehloro I Iodo
-

Example >

"
① [ 3
①
F!ndthelorgestcha!n
② put numbers
1- 3
2 methyl propane
② 2,3
d!methylhexa-nestartheref.l!
-

1
& 5
③
-

1
2
3
.

4>-6 7
2/
bd!methyl

3etnylooctane5tartfromth!s !desomostof.!t
8

get
the lowest numbers

The other 3- !sopropyl

way 6-
methyatane
④ 65
v3 21
2- chloro
3,4
d!methyl
7
g
8 6
ethyl
.
Noname
2 4 6

⑤
8

o 5
9

5-tert-butylnonanecyc.to
, 7

alkanes

Cnttzn
①
cycbpropane cyetoheptane

② cyelobutane cyebhexane
Examples
@ methyl cycbhexane

0
2 YOU SHOUL NUMBER

otherw!se

1,1-
d"methyl
cyclohexane

can be understood

examplex
s
eot
.-Ht
O
-H
(
resonance
)
touch the bounds
goudo not
s!gna
Week 3- I

Lecture
Phys!cal Propert!es of Alkanes

"ntermolecular
polar they have d!spers!ve
,;
non "nteract"ons
forces

no water
soluble !n

- more C more
electrons h!gher forces
when
;
;
more l!near
=

more SA

- fa ce area and
bo!l!ng po!nt
sur
conformat!ons of Alkanes

Irotamers streo!somers
Conformers are

same atom connect!v!ty but d!fferent spat!al arrangements

more stable

to
energy "s expected
be
h!gher

the
* are
always more
energet!c staggered
Ecl"psed
conformers of butane - "n m!dtern he m!ght ask
Example ,
met!la

cHt3
CHaCH
l cyclopentane

3t"l
f

-ethy1-2methy
The alphabat!c order "s
!mportant

.
Hocd
Gağatay
*

Conformat!on of Cyclalkane
most
favored andstable "s the cha!r conformat!on
More kolume bulk!er ( from H

d"fferent
)
Always put the bulk!er
group
to the
equarota!l
pos!t!on
.
cyclopropane cyclobutane cyclopentane

cyclopentane
cyclobutane

As seen
they are not planar

The molecules ( to be
changes "n order more stable
sn"fts)
cyclohexane

to
ure are
expected

draw
cyclohexane "n the

exam 5 }J X

less stable because !t "s

écl!psedò
Week 3- 2

Lecture
C!s Isomer!sm

-Trans
You cannot relocate
s!ngle bounds
on a
r!ng

stereo ""somer"sm dealls w"th molecules that have the some order of

attachment of the atoms but d!fference arrangements

.
,
C!s "somer"sm ( !somer!sm !s a k"nd of
geometr"c
-trans
)
stereo!somer!sm
.
cconst"tut"onal
d!fferent
structural "somer
bond pattern
Isomer
sare band

pattern

"nterconvertable
conformers rotamers

stereo"somers
.
not
"nterconvertable conf!gurat!onal "ssues

React!ons of alkanes

Combust!on

CH 2 CO theat (2128 kcallmol

)
2+2H20
4+202
C 12202-3 4 +5 theat (688.0 kcal!mol
H2O
4Htlot
)
C02
More react!ons

,
20 +4

tu+302-12C0
H20
carbon momox"de

CH - t

2H2O
4t02
C
carbon

cHutoa

-sCHzOtHaO
formaldehyde

ZCaHbtBOz

-x2CHgCOaHt2HzO
acet"c ac"d

Halogenat!on of Alkanes

chlor!nat!on

l"ght or

R CR!s alkane
neat

)
-H+CL-C-TR-CITHCI
CH a CH THCI
3CI
4tClz
methane chloromethane

Cl C Cl
CH CH CHC
2
CCl
2
2
13-s
2Cl2-5
3C1-5
4
tno one werts to deal w!th a m"xtare

swe need
pur!f!cat!on

cHz
-cHz-CHztClz-sCHzCHaCHaCl+CH3-CH-CH3
čı
tHCl
cha!n Mechan!sm
H Br

l!ght
tBrz tHßr

-
!n!t!at!on

2.
C!"
çî
-ç"
s

."

propegat!on
R TR
.TH-Cl
-HTCI
BîxçlmçlmîŞüc"tçİ
term!nat!on

~
T
ata
1-sC1-Cl
~ s
R
-tR-R-R
~ op

Rotel
-TR-CI
Week 4- t

lecture
Alkenes and
Alkynes
enttan CnHan

-2
C C =
=C
for example

cuttlo butane

-CECN
YFNFHSP
CUHto
CUHTO
If H
H
?
sp
2
s!gna and bounds
p!

cCrHPF
tH bound "s l!ke
p! a
1162
C
-C
Yf
H 111 wave
funct!on
Pa Pz
py
A
180 180
,11P4
"4 11
l
aa
H H c C HLG
-CEC-H
-H
bsp
'4 dsp !
"
î
If bond are less
sp

energet!c
 HH Every bond = satturated
C ethene
s!ngle

=C
fH Àt
You have

double
-
=
unsatturated

fr"ple
bounds
propene

butenex

l
put the plake of
l
3 I butene
-
the double bond
also
butene X

s
c!s DBe awave of
-2-butene
also x
butene c!s -trans
trans
-2-butene
2

3 ethyl methy
-4
^
1-2-pentene
}

4
But !t has a transle!s
5

But what !s trans to what

?
we need new
term!nology
.
-2-
pentene
- -3-
ethyl-4-methy,
zusammen t -3-
ethyl-4-methy,-2-pentene
T
b"g group b!gger

}
t
1-toro ethene

bromo-2-chloro-39
-t"odo
F
Br

trans ethene

-I-floro-2-"odo
I

trans 1,2- d""odo ethene

-
I

nave to
z 4
o4
3 cover the bond
2 L
w"th numbers

I "j

1,4-
cyclohexod"ene
cyclo hexene

conjugated double bonds

cummulated double bonds

I
@

,2 ç
=c=C'
£7 3

H YH
113- d"ene
cyclonexo
1,2-
pentad"ene
 Z

More
nam!ng
7

LI
2

"j
3

6- 1,3,7. octatr!ene
methyl
~
g
3 7
^

5
lo
6 Z
Z
4

516- 1,9-

d"v"ngl-
decad"enc
H
*

CCH
l

2
v!ryl Ha
c

CH
allyı
2
Cl
2

* 3- allyl chlor!de
chloropropene
3
 l
2

Z
l
Jakge
"!
ethyne
4

IY
üúv!
5

asetylenel
uose
-CEC-H
Iul

H
v!ngl

or
2-
cyclohexyl-I
propyne
=
v"ny1-1-cyclo
4-

H
3-

allyl-144-cycbhexod"ene
t-cyclotexene-3y1)
butene
pentene

-enty
çec
2-4 fbutern

3-41-
buten-2-y1J-I-yclohexene
.
 term!nal alkyne

ü 1-

butyne
- CEC Z butyne

Ine

-
^

pont

-f-en-4yne
We are bas!ng on the BOUND
DOUBLE

".
react!ons

I polar add!t!on

dl

Cl

R
tClz R

Br

Br
t Br 2
R R

Cl
Cl
TC
12
 Not to be !n the
exam
go!ng

tand Cl

8
-l
R
-
-

au
-

-
-

}
í

2
Cl
R ~
Cl

^£
aftuck

8
--
jBg
tBruBr } I
ßr

Br

Br

--
lßr
tBra )

ßr

el e

3
.

-\
tCl2
 2 water React!ons

t HzO I NOT GOING TO WORK

T T

H Hott !

+
-

H ethanol

-
T 2O
}
H e
2

olt

H
H
.

OHt
+
2O
t v

wrong

Markor states that " w"ll add

HY
rule
-n"kor
to the s"de where have more I
you
's
H ?
ólt
H ~
H
so
THT
w
H
o
0
t

tHâ CHz

stable
not stable

H H OH
H
+
p
+
H I
CHz
i
 H

why th!s "s not stable

*
H2
?
A ICHJ
not stable If

( CH
~ t
C
G

+
TY

CCH3+
CH3H
-
H HC

3
3

po
s

Z 30
carbocat!on

Ol

tH
3O
s
 week 4- 2

Lecture
Yats
F
tHa

-FX
-s
R

R
R

{ HBr
-
t
a
-sBV
Example

Şthx
-sYüt?
R
R

ottz olt

FtH
-oâ
H
+
-

s
}

R CH R
3
Quest!on

tHßr Br

you
w"ll
get
more of th"s one

Br

reg!oselect!v!ty

Otha rel tHTtCT

,
 OH

tHzOt )

Hydroborat!on

tBH s
)"YBHz
3
(
borane)
Naolt
olt HzOz
R

A BH
3
you should wr!te
everyth!ng
2 NaoHt H stepw!se
20a
,
R Baz
tRaB 1
-H
NaOtt
Haoz

R R
olt
r
Ha
Pt or
CH
3
R pd N! R
un

catalyst

Hz

Pt
 bouble Bound systems

@ Esolated

cojuga!ted
cumm!lated

tHX
}
X
H+
H d

Ec!
--.
.

f
the o rbym
stab!l!ty "s !ncreased the resonance

THBr rßr
3
Br

THBR t

Br

2 x
Hx
f H

x x
x

X
 Br

tBz
 Week 5- Lecture I
s"t
d!ol
tKMnOu H
}
R
ot

glycol

20
öff
R

H B
p !
H an
tOz )

R Aset!c
s
THTF
2

'H
~
o B

R Ac"de

oHf oH HT Hoot

,
kmnou
-

H
2O,0H
Off Olf

krunou

H
2o,OH
Ozonolys!s

tof Pg
T
l
-

e
0y
s
=a
ozon!de
2
)= )=0+ o Jn
o=
=
+
H

D H
03
Dzn!Ht T
0=
=0
+
H
i
 İğt o O

Oz .=
I
H
!!
Zn
,A3Øt
H

Alkene Ox!dat!on

P( pepox!de
-
-
s

)
-o-o"y
Add!t!on of HX to tr!ple bonds (

Alkynes)
x
R THX s
-CIC-R
H 1

Follow Markov rule

-n"kor
Cl
Ht

CHz +
}
HCI
H
-CEC-H
H
HI ì
s

enol
olt th!s !s
R THzot 3 R It not stable
-E-H
more

stable
{ " axsketone
i
 olt CH ott
!

3
Hoot
^

muHt
-- O

F !t CH

3
Add"t"on "s TRANS

Oxy mercurat!on
OH H

R
HgCOAC )
s
Hgloae
NaBHy
-E-H
Hz 2
0
)
é
HgCoAca
NABHY
2
FFPVT
H Hf olt
lBH BHz
R NaOHt
3
-CEC-H-
2 NaoHt H "
12 Hzoa k IH
2o2
,
H

BH Olf
31O
R NaoHt
H R
,
202
CEC
OHTH
-CH3
oHqup
20z
HPICHJ
!t
s

CH CH
3c"tö.
3
Ha add!t!on R R
Ha
12- = - 7
I
R
l!ndlars
H
H
catalyst
pa Cco

étt
3)
H H
I
tH LH
2-)
l"ndlars

catalyst

H
CHO -1
2
L"ndlar
!t IH
-CIG-CH3
catalyst

Xa add!t!on ( Br I
X=d,
)
,
R ßr

R
BRa lá
-CEGR'T
-Tbr
Cl

H C -
Cz
CIC-
I "
à

FBTbr
Br
frr
Bra
excess "
H z

Bra
3CEC-CH3
Br
 TNANH

2-JR-CEC
R Na

+
-CEC-H
term!nal alkyne
tNH

3
We not D!els Alder react!ons
are
respons!ble from

-
.
,
Rev!ew Quest!on
Br
Br
o f
start!ng mater"al for th"s compound "s made
up
!tonly cand
Cl

It should conta!n 4 carbons

Cconjugate Brb
Bo

HCl
.

v
add!t!on
X
8 8
adb!t!on Br Br

Rev!ew Quest!on Br
fst
ral
éCHt
Br 33 H
p
Brz "t HCl s

brt
}

p
w!ll attack Br
33
1033 3
2
nd
tr!ple bonds
rd
Br
al

CHtz x CHz
Br (
à
Br
Chapter 4- Compounds

Aromat"c
Cotto -7 th!s must be unsatturated
It doesn work w"th cntton

't
cn Han F

2
C Hto tBr not react

2-sd"d
6
so !t "s not unsatturated

I A
{ or
l
\ I
Kekule
structure

benzene

H!ghly hydrophob!c - w!ll to DNA

for H bonds
go
s
wr
w!ll cause mutat!ons

Aromat!c compounds have extra stab!l!ty

.
D!ffucult to mod!f!s
x F !rst !thas cyl!c
,
endless
cojugat!on
planar
sp hybr!d!zat!on
2
* 72 IT electrons
un
 xt cyl!eu
v
p endless
y
YH
H planer
HH
- non

-dromat"c
s
H Ht
I \
non aromat!c

î unt
2=4
n Cu!n electrons
à
ant!
-aromat"c
)
#ş
w -

dromat!c

"- yn kural!na
ant"-dromat"c
uyuyor
.
 Week 5- 2

lecture
Nomenelature of Aromat!cs

jCH
3
"n
o o cused
polystylene
(
t"ner"n
)
w

)
anamaddes"

benzene toluene cumene stylene

OCH F
OHt ( rad"cals
3
0H
captures
)
o o 0

!nRac
(
th!s "s

phenol an!sole benzaldenyde

.)
Aromat!o
OH
STABLE
compounds are

l ll

w!ll not turn !nto th!s

o

fo o

OH
INHz
o o o

acetophenone benzo!c ac!d an!l!ne

 I
cl Br
F
o o o
o

floro doro bromo !odo

benzene benzene benzene benzene

Hc 5 ş
3
methyl v!nyl
HCz CH 2
2-}
-
ethyl allyl

o
}
o
}
phenylCPh benz!llBnl
i
 Name these

Y
'.
o ethyl benzene I phenylethane

2- propanel !sopropyl benzene

phenyl
o

Noa
srotto
o o Yo
o

n"trobenzene benzene b!phenyl

sulfon!c ac!d

For two subs

!mortholo pos!t!on
-)
2
6

o
3
smetalm
-)
5
\
sparalp
-]
L

Cl

o o
-chlorotoluene
i
i
 Cl

o M

-d"chlorobenzene
Cl

Bßr
p "odo benzene
-bromo
o

Xylenes

o o
o

o m p
-xylene
-xylene
-xylene
!
-oHt
rS
benzene ac!d
1} p sulfon!c
-chloro
o
^
c
1
o

Olt
O benzo!c ac!d
o
-hydroxy
Ot
( ac!ds
sal"cyl"c
noa !
rNoz
t z

o 2,4.,6- I

tr"n"trotoluene
5 3
-
-

Noz

olt
f

I
o hydroxy
p
an!l!n am!no phenol
.
1

NHz

cl

H
! j
?
I
8
s
j! 2-

- 5-
chloro
T

eyelhexyl-4-"sopropylphend
I

PH
o
p phenol
-hydroxy
p
SH
-hydroqu"onone
spec!al name