⑥ 2 : otho , meta , para

[ .
diene .
(2) AlKon
∞ 10, 20130 ,
( ~

) ,
-

olldol, +[ )
(gdon nbenzen
⑥ Common Name

a + ≥ phenyl A- H2
(
Methyl alcohol
⑥
(
Λ
C 6 , ?
Ψ
-
(HacH2EH 3 -
clzcHalHaCH 3 Ha( =
CHC 2Ot allyl akohol

(propyl ) cbuthyl ) CH 3

,
CH 3 3 fert butyl allohol
( CH
-

-
-
3 3

(isopropyl ) ( Tsobuthyl )
aHOHO Ethyl glycol
N
-
NO -

NH 3 -
C≡

( nitro ) ( anino ) ( cyano) Benzonitrile HO CH Glycetol

0
-rk = -

CH = CH2 "
s
=
( -
so 3 H )

I allyll cVinyl ) Sulfobkc aETa

RIS
1 .
134
-
Oct3 -
0 ckCHzCH 3
2 .
4 → 5 .
→ R

sMefoxyl PVOByloXy
)
( 3) ether
-

caGzO
( 1) Benzene θ common llame
( hydroxyethyl ?
Common Name 1
bimethylether
3th

anrsole
\ \

Toluene
) ( phen ) ( Aniline ) (HF)
Tetra nydrofuran
[ HO L
A10
H 13
-
exher
\ \
23 O -
0Xy

Benzodenydel Benzoc acid ) Xylene)

3
\ \

( Acetophenone ) ( styrene )
 15 18) .

methyl
phenyl ,
θ
14 25)

b)
.

k( = = (H =
(HCH
3
Juseso
2
-phenyl -5-methylhexa X ane
-

→ 1. 3 ,5-Heptaf
τ dione -

ene .

Bromo
cHzcHaclls
|
(
d] Z

3
=
[ CH = CH
3 5 methy )
4

3 mo- 315- dimethylbenzene

1 o
-
-

cl3 mexhy/
← 1
!
bromo
→ 3 -topy 13 -

pentadiene
-
proby )

15 . )
2

anilrne O -

Bromopropylbenzene
! 2 3 4
15 19 ) praw strutanes
.
.

m -
Bromo chlon benzane (3 (uethylbuthyl ) bemzene
-

β- Bromoaniline (d ) 0 -
Aminobenzoc acid

(e) m -

Bromophend NO

.
tolmene
ethyl
(5) Trinitophen
.
2, 4 . 6 -

σ
}

1 4
NHa→ amino
K
Oito 5 l
2
No2 → nitro
3

P DTchlorotoluene 1 Etny1 2, 4 Dinthobenzene tettametthglbenzeme

1 , 13, 5
117 1 )
- - - -
-

* -

15 3) Draw
.
structuhes
| K 56
-

□ 3 ,

( b) P Bromotoluene
-

5 -Mexhyl -2 i
4
-nexanedT

(d) 1 -
chloro -
3. 5 -

dimethylbenzene

1 1
4,4 -

Bimefhy ) cyclonexan

1T
,
π 3
4

XBr BCVXX43

4 1Bromo 3
- -
.

methylphen
2
(
3

4
 phengl (6 36)
. IUPA ( .

-phenyl- -bufan

O
2 1Methgl - Ethyl I ethy lpropyl) ether
4 2

431
(a)
-

methgl CH2 CH 3
{
CH 3 CHzOH ( thCH3
s
3
|

}
4
ig
'
.
4
( b) P: ( p -

chlorophenyl ) ether
}
②
4
{ , s

:9
→ 3 ~
4
\

*
( 19 ( 25 ) ~
2 -

Bombcydopentan
1
2
-

cyclopenten | -

} ( d7 ( ylopentyl
oxy cylohexane

1
* E
(a)

T"
39 ) IUPAC .

ISy ydohexyl isopopyl

(b) salfide
(a)

f
( ) A-
→

( ~cHzCHOH
X
Epoxyiyclopentane
H * ( C]
)
1. 2 -

× ( n)
10
17 .

377 CHzc CH ☆
2.2 -

Dimethoxy propane
Cl ☆
( a) (

H0 -
2( Methy-1,4 - bufano
4 3

)
I 12
3 E+ny 1 2 hexan
cHnecH tk
-
- -

zc
4 5

(F] 2-

3romo 4 - -

cyanophen

= 4

☆
()
…
H
cis -
1 .3 -

cylobutanediol

.
 Ch.14 [Diels-Alder reaction]
ω Δ

[electrophilic additional reaction]

ErY oear 3

Br |
|

\
C C
1) (Z): cis- (E): trans-
P
…
" =
\

C C

oa
|
\

S C

TT
" - →
C \ =
ct 1 -
c - s

b
{ ocl 3
1 | Br
+ →
"
ND ( tl
"

[
"
E
Λ
C
icta / "
CH 3
3

{ H
1 |
1, 3 ButddteneMethyl (2) 2 butenoate Eisprodut
-
-
-

3
(
K
Ct
l
\ =
" _
ol 3
→
a
+
,
1
≈ "

b d
addTtTon - -
EHr \
~
←
1 i2 d 114
H 31 Crl 3
a E
b
, ≈ not formed
1. 3 -

Batadiene Methyl (E) -

2 -

butenoate
1 ,i 7

-pentadiene
{

nof formed
thans phoduG
≈
d
4
0 ≈ 7 *
+
↓ cr
dar

π ]
li2 addua 1 , 4 addutt

"

, ,…'
loEH 3
→
nre
rfeany
M µ

, :]
N Hr
" , thans
x
f

daddut ↓ 1.4 addua 2) Bycyclo-

,
1i2
M

,
N
"
"
*
"
π
∴…
113
-

cyclopentadrene Bycyclopentadrene
(4 .
28 ) Isoprehe ( 2 -
methy ) -
1,3 -

butadTane ) (S -
CTs]

B2 loctrophiisadditionVeactTon product
(4 3 | ] Diels -
AId .

13 β
.

= %) + r r +
Nr
>, (9) .

( 21 %) 176 % )
3% 21 % ?
+ "
* ≈
%
*
3
21 1
alkylTC CaurBonTcafion .

21 % 3/ 1 "
→
+
Y ,
I[
3 /1 211 .

"

76 %
3
④
~
% , 21
_
,

1 , a addut 1 . 4 addkot
x
.
( 4 32)
.
2. 3 -

37 -tert -buty 13
-

butadrene (4 43) .

Drels -
Alde ?

V .

→ SterTC strain
" → oXidative cleavage
.
S trans
-

*
strain polymer chain
.

Λ ,

DTels AId-
. H3 ( . }
H3 [ . H
C= C ] '
C= 0 + O = C
⑤π CHz "
' " "
2

14 40 ) .
Piels -

Alder ,

( 4 47 ) allene (H( =
( = (12) 200 -
400 mm UV
(a)
.

D
?
N
← .

conjugated .

V H

Λ
(D)

Λ K ;+
Λ CN
* Conjugated - → UV

*
.

↑
|
: : ← * A =
lg ]
= Ecl

~ [ε : .
C :
. l :
)
Co2als
(0
-

(d
) 3 : ←+
√

[ ]
(4 11 )
.
2
-

phenylbuta -
1 .3
-

drene segment of polyme

← … [ …

(4 (2) buta
.
-
1 .3 dTene
-
acid -

catalyzed poly merizatTon

mecanism .

-
aa ← '
 [aromatic ion]
Ch.15 |

cylopentanylanion :H +1 ,
*
[benzene] ( ycohepatrienylation : 1 * *
,

-
6 π (4nt 2 rule ]
-

conjugated drenes isolated dienes

Hyarog 6 k51 m .

<* ←<× <

H
" *, *
pyridine
H H _

→ Byriaine benzane .

6 p orbita' s from 6 π MOs :

π sustem

I aromafic
→
delocalized .
ion .

( ant 2 = , 0π - elesthons )
tal
t

plane
" ,
N 10ne pair :
ring SP .

→ dianion planar & regular octagon .

[Huckel’s 4n+2 rule] [Heterocyclic compounds]

, Λ -
lone pair aromaci+y ×

aromaci+y ×
m , π =
4n + 2 Λ 5
-

profondtion
M
aromacity
.

Pyridine
π =[ X 2)N
+ )
proto nation PY e

Δ
-

4π anaromas +y less stable

aromality
.

N
"

pyrrole

①
?
n
… 8
π fa
N _

faran
*
⑥
.
-
8 8
→ 4n+ 2
.

( H* ( repel ) distorted → 6π electons aromacity .

)
 32) cydoneptatriene ,

? ?"
∴n
cylopentatriene

⑥
.

O
"

π 6 → aromatil .
↓ Λ
"

caycloheptattrene cyclopenterdrene
[polycyclic aromacity compounds] → -
:S δ;
-

0
δ:
8 δ .
: :

*
1 118 +
*
+

Naphthalene ,
→
, <*
_ _
C B
B
Hnyaog
A
-
4 > 250K3 /m
cyloheptatrienone cydopentadlenone

Carbony |
.

B cyloheptatrienone ring ( 3× 2 6 ) = 6 π ,

□ )
Huckelrule - → atomatc
5x 2 = 10
π 4 nt 2 10 n cyclopentadienone ring (2 × 2 4] 4 π
= = = = ,

(
.

→ dromatic .
Huchel role X → honaomatic

33) (yclononatetacny| , ,

?
purine

→
KX2 8
10
=
,

π
N

-
-
H → 2

→ ahomatIc
"
~ .
>
radical anion
catron

8 o+ 1 =
9 At2 =
1ω
Aπ 9π (o eletrous
4H×2 . X X h= 2

Huckel14+2 ) ahion
3D] 3 cydopropeny ) ( (313)
.

E . <
ylopapeny | .

317 )Indole pyoe benzene

② gomatic heferocylis Compond Inde
.

Huckel aue aomatis ? Indole .

④ * (9) Indole π ?
-

-* -
f -
1←
nabhthalene ?
-. ( b) Indole
T
π π π
arom"
.

888
FKL
"
-

ovDit ☆

3
naphfalene
agyopropeny /
molecular orbrts cation radical anion "

Huckelule (afion
h) 4omatic
.

⑥ 8 4X 2 8
=
: NH → + 237

. ∴
. 10 π
.

lo)
Indole → atomatic

I )
cantion ant z= 2 o .

05 (4317
radilal ant 2 =
3 :

ahTon 4nt 2 =
4 8 5 *
.

.
43 ) (OX -
2 Bex
Ch.16
isoXazl ring . ?
× 1) electrophlic aromatic substitution
0
,

Is Xaz

.*
① Fluorination
Y BFT
2
CH 3
h
√
Bextra Λ F
NF
K 0 " (F TEBA BF4 ]
-

√
-

_ ω

{ ② Bromonation
.

FeB
NBr
6 ct s
→ π ,
I HBR |□ + H
6
alomafic .
242
2× =
, ) √

".Innmdrs
.

chlo

:
③ Tnation

" "
√
(2 , FaC3 "

④ Iodination

cuclk
NI
I 1 HI | | + HI
√ √

⑤ Ntronation NO
Hasoc
N
| | + H 103 | I + Hho
√ √

⑥ sulfonatron → reversible
SO3 H
^ ^
HasOE
I 1 + 503 | 1
√ √

④ mecanism

": tthsO 4 <

' sHSOx
π
salfur frioxiae

bunJ ←→
-
0
× -

"
*

Benzomesulfonic aEta

.
" .J
OFridel -

craft alkylatTon
"
(
,
∞
H CH3
| 1 + CH 31 . + [ r
-
z

√
√ " BZ )
$ CEl4
,
√ a ,

aromatis ring ) halogen ,

,
> 10 CarbonTcato
.

⑧ Fridel -
carft acylation

Λ NC clz
"
-
" knK
z
> 1
'a AI ' > √ √
Itanc 1
√
| + HCI

2)
H
Huy
NNO NNH
han
Λµ
2
+
2
-
1 Fe , H 3 O k NC
" " "
R
.

7
2 HO
-

√ .

√ √

benzaladehyde
① halogen [Reactivity] Benzan
nitro
benzoic akid ↑ Metoxy
jion -
Br F: "
↓ ElH ☆ δ∴ (43
TNosost
i
1 .

;
- - -

②N N- N
1 " 1
1 \
Nat N- X -
N m
1 " " | | |

" HrO " + NaCl - πR 3

-
C v
" -
i

"
.
-

√ √
, ocses ,

| |
NO Drthodpura DrAnod para
NOr Meta- diremcting deactTvatDos
dtreakting altTvators
dtrecting
deactTvatoos

③
→ benzy |
,

Br '
+
√
. - NaBr

COt

T Mnox
3
,

√
 ( 0 4n)
.

benzene ?

(a) Bromobenzene (b) BenEOnTLTe.

. ( C) Benzoic acid

(d) Nittobenzen .( e )Benzenesulfonrc actd

(fl Methoxy benzene

"

fridelcraff acylaton ) + ,
CHsc
☆ +

:
,
A- B γ
a
)
√
'
OP

A-U
(
()
←
Ψ √
f
√

benzomTtrTle
m
s

(a) A- 02 H (103 A- c0
H 2sO4
1
√ √
m
ioz
-00

'
-1 N0
(d) * Hs
√
r
(a) 4 -
1
-
2 3 -
(b) 1 2
- -
3 -

4 ( )2 - -
3 4

- 1
A50
. .

s0
*
HN 0 n
le) 3
1 . 11
Hasoa √
√

m
Noz

A-0 A- 043
*
0 ) HN 03
-

I 1. λ
' +
Haso4
√ -
No √

P
lior
Br Br Br
(a) | 1 NO |
so |
N-
1 +

Br outhod pard .
s * fridel -

Craft alkylation
NO NOz
|
3
. '
-

NOr m
m (a)

( c)
,. +
×
| tsC
+ Oip

.
|
- on odp
)

.+ H3 C

reaETVy > Br
Amino EWET

p aVomatic hing

Ea) ethyl allyl ketone

-N
π V
H

k H
.

1X
*
rhan '
α
N
(d )
T
- → .

↑ √
a lttl

I 3 9VO X'
,
n X1
No N0z
Loip
CH 3 0 -
ethslaniline
() 1
*- cH 3cl A- ()1 . Nto 2 .
nitro
3
a
4 6 AIl 13 H A- NHα
+
a d
c
+
t 6 A- NOQ I .Fe ,HBO
EILOH Ψ 2 .
Ok
-

Ψ
oip
N Nα
1 - -
TBr
'
() 1 , T>
n
Br
.

,
AIC3
+
oip

(g)
A~
s03 e +,
i

vBr
)
Ivoz -uH
.

Al 3 .

C ( ()
Br
) cHncl H
A 3 - ④ 1
A- CO

Alty
) ,
Hro
~
√
↑
√
4" Br e Bγ
,

Ami @ -INH
" α
2

mthctzct
(a )
π - ctrcbiebls
T

EWG - -

CI ( ) Ally I
\
.

' '
-
N 02 - =☆ - CN ocl s Voc s

(Roactivity : CIEOH +
D. P

- s) .

\
loctH 3
 (a )
,

aX
i" ,

") ,
(
λ
) T

\
√
oip
Noz
, ~

1 . ×1
() 1002
BE , EeBB
T
-
.
'
:
All3 Nso →
℃
1
-
glzcl3

ioz {
1. ① ?- t
1. ↑- |
m

e. .
(K)
A~ 503
()

OsP
. X" . , Br
,
303
,H
-
2soa
>
XSOH
↑
uBr
X
" 10
(d) ) , - 5n Benzene toluene

?
N2
:
NL

-
.
s 4 nitotoluene
(9) 23romo -
-

α
CH 3
A-
"( =
"
3

o
Br
H3
*- A-
,
→ .
↑
.
benzene |
Br
.
56 "
√
5
?
.
- I
.

(() 2,4. 0 Fribomoaniline

(a) hlonacetopheone
-

p -
(

()m - BromonTtobenzene

,
[
*
HmH.
sox - .
,
,
( c) 0 -

Bromobenzenesulfontc acrd .
:"
(a ) m -
chlon benzenesulfonTl acrd
ni "

anilnin
X
.

"! .
64 Benzene
? Ch.17
*
* ( CH3) 3 (
aCrl ☆
3H
( H Br [H ☆
| |

. ,
. ,
ab
. . "
CH 3 i
↓ ↓
CF CH 2 H

n4
p AmTnophen . d
a n e .

. -
-IH 2

CH 3 SH ) EDG

n, P -

Methyl phenl -(
h
.

γ
pheno
-1
chlorophen )
,
0 d P -

EWG

√ P -

Nitrophen -

NO .

O
⑦
B
. Z F

③ ④ ① ③
( a ) EH , CHa cod , AlKl 3

( b) H2 , pd / C ② -
☆H
> IEDG] ③ 3 ①

(C ) Br 2
,
FeBrs ② ③ ①
1 h- cceaoal

( d) NBS , ( ph (oz] 2 √

( e) KOH ,
efhan ↑ .

>

: ,
Λ
.
 I7 4a ) yclopentan ?
4m) 2 -

pheny lethan ?

( a)
(a) ydopentanone
(
styrene

Alk
(
POCs N
=
(H '
Ψ pyridTne
'
Ψ
styrene
(b) cyclopentene

() 2clO
AlH
A
→
pefTodiane
CHal
'
→
ne '
phenyl acetuldehyde
_

5)

π-
( (]
,
( Ha C0
[ro . A~
H 3Ot, acetone
Ψ

phenylaletic acid
.s04

(d ) - I0
V >
H
- (
3

* 4

Ψ Mn ,

5)
Benzoic act@
C0 C0
Λ≈ H
Λ~
[e) EthylBenzene Ψ PallC
from( al ,

CHO
. 0.
-
=

2 zn , H 3 Ot
,
0 1 . π AIH 4 Λ~ H
. √ Λ≈ , |
2
Hnt √
Benzaldenyde
.

stgnene √

(g) 1 -pmenylethan

from( al ,

{
(H = CHz
1 (4 g (oAc ) 2 ,Ho ,

-
.

>
2 . NUBH 4

stgrene
( n ) 1 3romo
-
-
2 -

phenylethane
2h
AH PBr3 AlH2hB
"
→