Summary Chapter 13 - Alkenes

AL R E N E S
V N S A T V RA T E D H Y D R OC A R B ON S
I DO U B h E C C B OND
f O R M U L A nHzn
CAN BE B R A N L H t D AC Y C h l C C Y C h l C
SOME CYCLIC ALKENES DO NOT OBEY
GEN FORMULA AS MORE THAN 1
DOUBLE BOND

N A T V R E Of DO V B LE B OND
t A l H C AR B ON AT M O HA S 4 E h E C T R O N S IN
OU T E R S H E L L
314 t h E L T R O N S O l C U P l E D I N 3 6 BONDS
I T O OT H t R C A R BO N I N DO V B h t BO N D
t O T H E R 2 A T O MS C Cl H
l E h EC T R O N L E f t O C C U P I t D I N p O R BI T AL
IT B O N D f O RM E D B Y S I D t w A Y S O V E R L A P
Of L p OR B I T A L S
I f R OM E A l H l A R B O N A T O M Of D OV B L E
BO N D
E A L H C AT O M l O N T R i B V T E S 1 ELECTRO N
T O PA l R I N DO V B E BO N DL
IT E L E C T RO N D E N S I T Y C O N C E N T R A T t D
A BO V E t Bt h O W L I N E d 0 I N I NG NU l h t l
Of B O N D I N G A T OM S

TI B O N D hO C K S 2 L A R B O N A T OM S I N
P O S I T l O N t P R t V t N T S RO T A T 1 ON AR0 U ND
DO V B h t B O N D
S O G E O ME T R Y D I f f t R t N T TO A L H A NE S
W H E R t R O T A T l O N PO S S I B h t A R OU N D
E AL H A T OM
FORMED BYOVERLAP Of P ORBITALS
H BE B H SIDEWAYS AS PERPENDICULAR TO INTERNUCLEAR
t
C C i H AXIS
to H C C H H
i
g SH C T BOND
Xp ORBITAL H
XpOVERLAP
ORBITALS
ABOVE
HO OH
IT BOND
BELOW CHAIN Of Pr ORBITALS AN OVERLAP TO
1 ATOMS FORMTRIPLEBONDS 121T BONDS
I 6 BOND
S HAPE A R OU N D DO V B h t BON D
T R I G ON A L PL A N AR A S
3 RE G l O NS Of E h f C T R O N D t NS I T Y
AR O U N D E AC H C ATO M
3 R t G l O NS RE Pt h EA C H O T H E R S O t A k t

, S
PO I T O
S l N I N S PA l t A s t A R A P A R T AS
PO S S I B L E L l 20 M U T V A L l N T E R A l T l O N S
MI N I MI S t D
A L L A T OM S I N S A ME PL A NE

P H YS l C A L PR OPt R t I t s
S I M I L A R t 0 A L KA N t S
l BO I L I N G P O l N T
LO N G E R C l HA l N M B P T AS MO R E A T OM S
J O MO R E I N D U C t D D I P O L E D l PO h E
I N t t RA l T l O N S A S MO R E C O N T AC T M I m 1 SO
MO R E E N E R GY NEE D ED TO O V t R l O M E
M B RAN C H t D WB P T AS f t wt r p O l N T S Of
CONT A l t L I N D UC t D D I P OL t DI POL t
I N T t R A l T l 0 NS

2 ME L T I N G P O IN T
G t N t RA L I N C R E AS E W I TH MO L E L V L A R MASS
3 SOL UB I L I T Y
NO N PO L A R S O l MM I S f l B L E W I T H WA T E R
MI S S I B h t W I T H O R G A N l c S O L V t N T S

I S OM t R I S M I N A LN E N t s
1ST R V C T U RAL
PO S I T l O N O f DO V B L E BO N D CH A N G E S
B R A N CH I N G O C C U RS
CG PENT l ENE EGPENT 2 ENE EG 3METHYLBUT I ENT
H H H H
it it itCitCit fl fl l l I H
i
CC H H CC C C CH f C C Ci H
i l I i l
f f HH H H H H H H
H CH
H

H
2 GE O M E T R l l A L
E XA M p h f Of S T E R t O l S 0 ME R I S M
I N A L K E N ES
O CC U R S DU E TO RE S T R l l T E D ROT A T l O N
Of C C BO N DS
T WO f O R M S

I If SIMILAR ATOMS1GROUPS
ATTACHED TO END Of fC
i CANNOT HAVE 1151TRANS
I ISOMERISM BUT STILL th
IS 2 TRANS t SHAPES MUST BE DIFFERENT
GROUPS1
ATOMSONSAME GROUPSATOMS OPPOSITE CIS CAN BE C12 AND
SIDEOfDOUBLE SIDE Of DOUBLE BOND TRANSCANBE C12