fly 1 :

STRUCTURE i. BONDING

of carbon
organic chemistry is
study
'

carbon can make single , double ,

and triple bonds

ke
'

se :
-

alkane alkene e cyclo alkane

Bonds
•
covalent bonds : share electrons .
ionic bonds : transfer of electrons
Na e
-0
NCH
j NaCl
.
- t

t CI :-O
-0
H H H t e
-
-
• -
H :
- .
. -

cation apian
t

Polarization
Polarization results in a dipole
1-

At Bt o
electronegativity pull : an atom has on bonded e
-

pair
y Ennore

minutely
i÷iF¥÷÷.iq:9
electro
neg .

f-

,
.

in :*:
one

www.wurs
 How to Draw Lewis structure

step 1 :
Count total number of valence electrons available

cation subtract based charge

-
•

e
-

-
on

anion : add e based charge

-

on
•

step 2 : Draw molecular skeleton

Step 3: Depict all covalent bonds as lines connecting atoms

additional surround central atom

-
•
all e

step 4 Assign formal charge atoms in molecule

:
to

C-lementvdlehcee-H-bondsttlonepc.li#

:L :'t : :L
(
t = 8 O

: : :
halides : f. Cl Br I t ' 8 3
, .

↳
satisfy octet Rule

' '

likes determined
what an atom
by position on periodic table
-

C.
g . Hz NCOOH

It can only have 1 bond :O : * check if structure is correct

ll

N likes 3 bonds H -
N - C -
O H -

by assigning formal charge and

-

I
,

C likes 4 bonds H add to see if equal net

charge
O likes 2 bonds

FC (valence ) (H bonds ) ( non bonding )

-

e e
- -
- - -

N S -
3 -

2=0 Practice :

⑤
H l -
I -

O
'
-
O all hydrogen l . ) NH 4
⑤
C 4 -
4 -
0=0 2 . ) ( 03
O G -
2 -
4=0 double bond 3.) CICOC H2 CH 2MHz
O G 2 4 Ising le bond
- -

0 →
net charge
Solutions

Ein
I . ) H " "

ion
o

"
.

" :
i .

"

quiz one material

① ke Kille Lewis structure bonds and
using lines to represent covalent
:

shows all atoms with lone pairs

H H H H H
l l l l l

H
-

C C -
-

C C -
-

C
-

O -

H
a o
l l l
l ,
H H H H H

② condensed : all atoms are written out to communicate structure w/o

drawing out chemical bonds

CH3CH2CHzCH2CH2 OH or CH 3 ( CH 2) 4 OH

parenthesis :
•
condense long chain of hydrocarbons (
usually at least 4 -
CH z )
can tell its hot part of main chain of carbons
you
•

ex )

Cl -

GHz
-
CICHZCHZCHCCH 3) Cttzcttz main chain : longest chain of
carbons

③ Bond line bonds w/o hydrogens

shows
writing out carbons or
:

# OH

'

-
each end t bend represents a carbon

↳
Hydrogens are not drawn in ( unless on an atom besides carbon )
PRACTICE :
in structure ? How ?
1.) HOW many carbons are
Following many hydrogens
(d) ~ Cdl O

Et Li
(b) cel
if ' -re

y
( Cl le Br
o
,
Ift
Myth Cl

2.) write ke Kyle structure for each of following molecule .

(d) CHZCHCONOHCHCH 2 ( b) ( Cl CH3CCCHCICH2.CH/CH3)CONHz

ryno
T

3) write condensed formula

ion -
unit .

II It .E=E⇐c÷÷¥iI .

H
"

f H
-

H
-

H -
C -

H
H
H

H -
E -
H H

H -
'

c -
H
H -

§ -
y

!! ! icy
O O
it ft ft
N' w
-
'

c'
'

( Cl Cdl H - - -
c -
c -
c -
- c -
c -
- c -
-
H
l l l l
Br H H H

-
t
o
)
( et fry've 1ft
Ferro
Br H
41 Write bond line structure
( Q ) CH 3 COOCH 2 CHCCHZCHZCH 3) CHZCHICHOHCCCH 3) 3

(b) CHCH ( CH 216 CH ( ( H2 ( H2 NH 2) COOH

( C) ( CH3CHzl3C( CH 214 CHCICHCHCHZ COOCH ( CH 3) z

(d) CH 3 ( CC ( CH 312 CH z NHC H2 ( H2 CH ( CH 3) 2 COCH 3

5) What is the formal charge of each atom

:O
-
H

H :O :
,

i. NEN -1×40 .

I .
.
:

H f ' '

H " :

HN H

t't
 NOTES : * carbon makes 4 bonds

solutions : •
carbon triple bond
' • ' ' " " oh

"" '

carbon doubleton
'd .

(d)
•

Cdl
•

- C :O O C :
4
htt it :O
LY H :8

(b) c :S cel C: 7
ya '

Y
'
Hilo H : 15

( Cl le C
'
-
G Br
o
,
H : 10 Ifl
f\ty Cl
C

H
:
12
:
20

2.) write Kekllle structure for each of following molecule .

(d) CHZCHCONOHCHCHZ ( b) (C) CH3C.CC/tClCH2CHlCH3)CONHz

ryno

it
T

÷÷÷÷÷÷:÷÷÷÷t÷÷÷÷÷i÷:*:i⇐÷i÷÷÷÷÷i÷÷i
.ci;
it
it
:
" . . "
"

l l
"
H .
. c -
c
C l
- -
C- ft
H '
c -

H
H .

3) write condensed formula

on unit .

II It .E=E-⇐c÷÷÷÷I H
.
"

f H
-

H
-

( H-3CHzcclzcttzc.CC H2 -

C
H -
-

H
'
CHCCHZOHICHZCHZCH 3 -

H CH3CHzCHz CHOHCHCCHZCH 3) CHCH -

H CCCH2CHzCH3
'

H -
c -
H H

HH §
' -
-
y
H
c
- -

H H 0 O
l it it it
N' w
-
l l l ll

(C) Cd ) H -
C -
C -
C -
C -
c -
c -
- C -
c -
- C -
c -
H
, l l l l l l

H H H Br H H H

(CH 3) 2CHCHZCHZCONCCH31-CCH3CHzlzCHCHB.hr CHIOCH 3) CHCHCHCHCHO

( H2CHzCH2CH3

-
I
o
7
(e) fry've 1ft
~€~oH
Br
( CH 3) 3CCHzCH2CHBrCHl0CH2CH3) -

( CH3CHz)zCHCClCHz)yOH
CHZCHCHZ
41 Write bond line structure
( Q ) CH 3 COOCH 2 CHCCHZCHZCH 3) CHZCHICHOHCCCH 3) 3
condensed - bond line
OH -

f÷ i ÷ ÷ ÷
NOTES
one,¥¥ flashcards)
( make

(b) CHZCHCCHZIBCHCCHZCH 2MHz) COOH -

CHZCH -
-
# →
alkene

CHxCCCH×→ # alkyne
-
→
o

Colts aromatic
f+
IN OH → -
-

NH z
-

CHZOH →
* OH - alcohol
-

CHZOCH z -
>
Fo -
X -
ether
-

CH z SH -
TSH →
-
thiol
"'

n'
' """
"" " " " '

::÷÷
.

CHO →
aldehyde
-
→
It

COCH × → →
ketone
-

COOH →
OH →
carboxylic acid
COOCH of ester
-

x →
(d) CH3CCCCCH312CHZNHCHZCHZCCCH.dz COCH ,
-

cool →
c, →
acyl halide
0 ( Br
it
or I)

-
#t
anhydride
→
coo co →
-

o
-

¥NHz→l amide
'
-

CON Hz →

CONHCHX -
thirty - 2
'

amide
-

CONHCCHXICHX Ntt → 3- amide

-

CN →
to N -
nitrile
5) What is the formal charge of each atom
-

2
H
FC (valence I (H bonds ) ( non bonding )
'
- -

① o e e
'
- -
- - -

'
II :O :
I
-0
i.
NEON IT:O : z
l) S -

4 -
O -
-
+
I
H f

/-
' '

" 4 :
2) 6 -
3 -
2=+1

3)
-

It H G -

I -
f = -

I
,
4 H 4) S -

3 -

2 = 0
 quiz one material part 2

*
Resonance AA FA
you fully topic I
understand
( spend time on this make sure

I DON 'T MEMORIZE ! Foundation for ! success in 118 )

describe delocalization of e can 't

-

•
Resonance : min a molecule that

be illustrate w/ 1 Lewis structure

↳ delocalization spread molecule
-

: e out over

molecule is not
resonating back l forth through all different
forms but actual structure is hybrid of all forms
structures differ placement of
-

resonance in e
only
-

and riot movement of atoms

↳ when
drawing don't try to move atoms

Rules to Draw Resonance Structures * never break a single bond

* never exceed octet for 2nd

1) Atoms never move triple bond ) ( C. N Fl

fcdouble or row elements ,
O
,

21
-

in bond lone ↳ ( bonds )

Only move e IT or pair t Clone pairs ) can

3) Overall net
charge remains same never exceed 4

4) Don 't change framework Of bonds

pushing arrow ! end of
-

f : e arrow
starts at e source t head of arrow shows
-

EX ) CH 3 NO 2 where e are going

-

↳
Draw ke Kull

"
always start at lone pair

ft
②

)
↳ be electron

iii.
charge
①
Hf neg formal even better

iii. i
.

-
it .
o: rich
→
'
①
It 2) a
signify structures are resonance forms
charge :O net
net charge o
-
-

Real Hybrid
"

ft Ii-

of
a. oui .
electrons
ion -
even .name distribution
 Major 1 Minor contributor

major minor
8-
⑦ formal charge :
' .
more stable .
less stable
extra e -0 lone pair '

↳ start arrow here .

less formal charge .
more charges
•
Charge 0h EN atoms .
charge on carbon → most minor !
⑤ formal charge :

happy
↳ ↳ unstable
Oxygen l nitrogen t not
"
absence e -0
'
lone pair

↳ push e -

here !

symmetric molecules are equal contributors

•

Practice :

1.) Draw kekule structure t resonance forms

(d) CH 3 CH 2 CONHCH 3

(b) Co Hii CONH

(C) CH 3 CHCH COCH 3

2) Draw Resonance structures and tell if major 1 minor contributor
⑤

( al -

I .
-
Otc .

(b)
①
I

(c) xx

loll
rain
-

let in
u

(f)
IT?'
- N
H

:O :
11
191 ifni
- -

( ht
n:

( it to
H X
1=1

( jl o
( K) -n

Tko --

(1) -- o
In

5 Patterns to recognize once master resonance

1) Lone pair next to a pi bond

He
""
-

(b)

(Ed T

( riff
" "

-
o_0

2) A lone pair next to positive charge

(
(d)
-
o
- a-

"'

f
-
'
-

Info
(f) -0
-
 3) A pi bond next to positive charge

f
'
9' ←

III
"" .
-

f
lil →
to

4) A pi bond between two atoms where one atom is electronegative

cjsfyny →

( Eye
""

( l)

( c-

5) Pi bonds all the way around ring

go

'f
im t

f
""

e-
Solutions

1. I Draw Ke Ku le structure t resonance for ms

( d) C H 3 C H 2 CONHC H3

it -
it .

iii. ¥ .
- it .

.
iii. I

(b) C o H i i CONH

f i - it .
-
-
it c- ii. it
)
( C) C H 3 C H C HCOCH 3

I .
÷: " -
it
i iii. I
 2) Draw Resonance structures and tell if major 1 minor contributor

)
⑤

Cal →
=
equal contributors
①

inform ]
'

-
. a

minor super minor major

fix EE Exo )
'" -
. -

major super minor super minor

ldlfrfti-e-f.hn
major minor
- →
#
minor
F- )
'"

f a

I
major super minor minor

E.n.io?- )
"' c-

major minor minor

)
:O :

Cgl c- - a -

W
major super minor minor

""
f minor
n:
- new -0
major )
"'

fEE - -
'

EET )
÷:#
bond
in
~

to

( j) →
Aft c- ¥ ) all equal contributes
 FEET )
""
÷
-

. .

major supermini or minor

09

Hf )
( - ou -
- EEE -
-
¥
major super minor minor

1) Lone pair next to a pi bond

Hoo E )
""
-

"d
as
o⑤ )
finn: in
:o)
" -

'

'

. .

2) A lone pair next to positive charge

f )
""

I
( e) ①I

f-
-

to

fat )
(f) mo
:O :O -
 3) A pi bond next to positive charge
"
( EEE CEE EF )
"
- -

f )
⑦
""

IE Th
-

( )
"' to
Esto
-

41 A pi bond between two atoms where one atom is electronegative

( )
(
jl Yun Y T
toy T

f )
"" '

← Eto

:o)
"'

fo -

on

5) Pi bonds all the way around ring

go

)
' m' -
'

( )
IN
A
e-
FEET -

o
to -
°