Naming Organic

Molecules

prefer stem susjet

↓ ↓ ↳ from functional

L
from other
from number group
Igroups functional
t
carbons
of alkane (ane)
askene
must branches ↳ (-ene)
GES
in
number alcohol (01)
carbons! eg. acid
carboxylic acid)
foic
and location aldehyde ( a)

meansth
-

14-methylhexane
of main keytone (-one)
functional ester (-oate)
group
↓betweennumbersand word e eg. but-1-01

(c-c) enes( d) =

kanes
1 7 1

Hi(H I

H -
C -

C -

C -

C -
H + -
-
-

-
-

i
I I
i
I

H HH 1

butane but-2-ene
I I
4 C's allane ↓↓4 alkene
4 C's on
-

in chain and
H c
I

-
H
11 1

H -
-
-
-
H -

k -

H
I
Hi
k
I I

-
- -
HH H H
H

-
H

3-dimentandanene
I

n -

methyl H
H
c's2 and 3
on
longest
chain
3-methylpent-2-ene alkene
↓
methyl
↓ge's-End,
3rd in longest
group on chain
 lkanes(c -x) #hols (-0H)
halogerie,so label Q Fratogen H

Carbon
from
numbers
carbon closest
to
starting I I
H
,A
hatogen H -
C -

C -

C -

C -

C H -

I I I
I I
H
H H

*
1 H

-
-
-
-n pent-2-ol
I
-
-

↓it it i -
OH OR
2 carbon
2-chlorobutane H
H

-"--n
I I
chlorine
on 2nd
carbon
I I

H Br H

- -ni
I
11 i i
H - C C - -

C -

Hi I H
1-

3,5-dimethylhex-2-01
22 ranopropane
2 bromine's
both
on 2nd
carbon
cycloalkanes( -c)
H2 H
Carboxylic Acids (-200H) C
H
I
H
I -O c
I
forms 1-
"a -

-H
-

W
H -

C -

C -
C Partofwhole
-0 -
H
chain
-
C
H H
-

H
1-H
H

propanoic acid ↓ cyclopentane

2 less It's than a

alkane
Straight chain

-= -c (as C's are

joined at
the end
-8 -
H

but-2-enoic acid aliphatic

↳ hydrocarbons in

Strait/branched chains
aromatic compounds or a non-aromatic
a benzene
contain ring ring
hisithas
itis
ring
!

a
I
also
alicyclic
 I
somers

Structural Isomerism

Same molecular formula but

differentstructural formula
↳ atoms
arranged in

a differentway
chain isomers
①nee

Karbon Skeleton
arranged disserently)
branched chains
eg. H

! III
H -

4 -
H

H C C C C C -

C H
-C
-

4,
- - -
-
-
-

11 l 11 l 1

H H H H H H 1

H C- -c
C
C H
- -
-

CoH,4 (hexane) Hi H
I I
H

CH,4 (2-ethylbutane)

②mal
isomers

(functional group in differentplace)

eg. H H 1 HH H 1
H I
11
cb 1
-
W
c
=
H 1
cH
=
- -
-
-

1
I H

C4H8(but-1-ene) C4H8(but-2-ene)

③agroup l
isomers

latoms arranged into differentfunctional groups)

H H alkane H

eg.
H H -
H x
C
6
I
- S
I W
~H
+ c c H C
-
- -
- - -
=

1
- n
1
auene it ↓ i
-n
it
-

Cglt,o (pent-z-ene)
CsHio (cyclopentane)
 I
somers
Stereoisomers
same structural formula but
differentarrangementin space
↳
caused
by restricted
rotation around double
①somers band

E -

high priority groups on

opposite sides

H Y
eg.
c
c
=
Cl

=
=

-
H c
X
B has a

↳ higher
high priority
atomic
2 or has
groups Br
-

number than
Same side a
higher
atomic number than Itakes priority)
H
C1 (takes priority)
4

x
- Br are on differentsides of
c
=
double band (Eisamer)
W
X y

② isomers
↳ E12 isomerism
type of
where the two catoms

making up the double

bond have one

in comman
group
H
H 1
Same
groups
W -

cx
on
other groups
=

- same side
-Cis-isomer

H
W ~ " other
groups
sides
on

cC different
*

* W -
- trans-isomer
I
 Reaction
Mechanisms
show step by step -Types
of
electrons
movements of Reaction
-

in reaction
an
organic substitution
Addition
Elimination
Curly
- a
Arrows

movement
elections
of
electron Reaction
↳- pair Intermediates

↳-San ↳ temporary products

be shown to come
as partof
the steps
must
in the mechanism to
from originating electrons
products
form the overall
↳
eg. · r
Br of the reaction

Cl -
Cl
4

electrophile -

have a low electron

density (t)
↳
attracted to -

ceketron pair acceptor)

nucleophile -

have a
high
(
electron

density
↳ attack electrophiles
and donate electrons
 Alkanes
CnHen+2 o-band
a CC
_

c C
single bonds,
-

all
So
-
orbitals
directly Seeata
-
re
overlap
Tetrahedral Shape
~>
can form
H H each catam 4covalent
-- C: IS22s 2p2 bands to
has 4 bonding IS' rach 2P
6
H C C H electron pairs H:
around it
H H Low Reactivity
↳ high bond enthalpy
Boiling points increase strong)
bonds
down the
homologous non-polar
series

↳
due to increased
branched chains London forces
have lower
boiling ↳ chains
points, as they larger
larger surface
can'tpack
together
-

area to interact
as much and form induced
(fewer surface dipole dipole
-

interactions) interactions

combustion

Complete
lenough oxygen)
=
alkane
oxygen-backdetwater
+

incomplete
(not enough oxygen) alkane
=

+
oxygen-det watert
carbon
particulates

↓ binds to
haemoglobin
better than
oxygen
-very toxic

loxygen deprivation)
 Fadical a
atom/group
single unpaired
withthe

↳ atom
compound replaced
in a
entran
reactive
Haloalkanes by very
Forming
as
another
↳ H in alkane
wants to find another
electron for pair
substituted with
forming a
halogen
chloromethane: reaction started by

CH4 +C12
oCHyC
wlight
HCI
+
(photochemical)

①nation
-
-1 =2c:
-

c
W

homolytic fission

② ation (collisions thatkeep chain reaction

going-they form radicals)
in
H

1.
H ci-H H CI
C
- -

H +
-

C I -

I
H H
then collides
-
-

with....
H

-
. d -> n-c-ci +
Co

H i

③ ation (explorescolisesthatstop citie

-
ms
*
.
HH
, 1
- r-c-c-
-

habalkane can

it i reactwith radical
i
again forming new

products
ci i-c -
c leg. dichloromethane)
H H -
reaction can happen
I at
H -
c. +

ci -
H - -
c any pointalong
chain andform lots
i i of isomers
 Alkenes
CnHan Bond
W
-

c C
=

one 8 band
(Sigma)
and (pi)
one

weaker than O, as
further from nucleus

C 152522p4
=

↓ already
filled (no change
etivity
-

↳ 11 1 1 (1st ()
double bond=
reactive
ir 1 T(2nd()
very
c C =
** E]
↳)two
pairs of - I
electrons

-]
=

high electron -

density o bond
① - F overlap)
(direct
-H
CO2

g
H -H
↳ bond
sticks out

-
to be attacked I see 3rd
likely orbital
by particles with a low
snow

ot
electron
density
(electrophiles)

② low bond
enthalpy bond

ofa bond = Corbital bends)

easier to break

rotate
cannot around
band, as in orbitals
for
Test unsaturation in same position
must
stay
+O overlap
add bromine water (orange)
H
will turn less isC=C is
present W
F
-H
↳ as Br isadded
CO2

H -H
to
hydrocarbon
chain

Selectrophilic addition)
(planar)
 Electrophilic Addition
Reactions
Polar band
Electrophiles have a low electron
H
attracted

!
density and
double bond
are to
...........
the
(high electron
density) -
H i H

eg. Hist
I
H
--
st
L
·
7
H*c15 H

S
C C -

Br
electrons
-
-

H
I
bond
5-in
=
x
H
attracted
to
electrophile

The
nucpophilated
double bond is electrons
forced further makes
to place a
with a low electron towards Y Xst
=

density
H

-
H H
W
I I

↳ -
-
-

&

-
& ②
X
Y
·
carbon
lest +

charged,
↳ as is took
elections in the
② when new band
① bond to form
2electfrom dee is
X-Y
formed, the
bond
bond with X

breaks
Karbocation)
new
- band between (hetrolytic
Cand X Fission) ↓
one atam
takes both electrons
in the bond

H H H H
x y molecule
I I
-

e I I could be:
C C Nicatalyst)
H ) C H
-
H -

H
s
-
-

e
- -
-

I 150°
I I
e -
-
W
X X
H- H
<I-c
(ackand
(dichloroalkane

③ y ion is a nucleophile and attacks the

positive carbon (donates lone pair and farms band)

eg. Forming haloalkanes

HH
11

c
*
- -> -
c
-
-
- -
= - -
n

H ↓ :
I
Br
s H

(bromoethane)
 Markownikoff's
Rule
when a hydrogen halide
W
added
W

is to
unsymmetrical
an

alkene, differentisomers can H H H H

I I
form H -
c -

c - - -
n

eg. - did it
I H H

i= 6
11
-

c - -
H
+
-

c -chlorobutane
it i
= H H H H
but-1-ene 11 11
H -
c -

c -

C -

C -
H

11
H ci
it
amount
ofeach isomer 2-chlorobutane
depends stability
of
on

(major product)
the carbocation the

halogen bonds to

↳ 3 possible carbocations:

H
R
↑
R
R =

4 -

H R =

C
-
H R =

C R
+

primary secondary tertiary

R- alkyl groups
e
c with more alkyl
more stable,
groups are
as the alkyl group's
elections can move

closer and
to it stabilise
the
charge
+

(more
more stable carbocations alkyl groups)
St
are more
likely to form during the 1
step of the mechanism,so most products will
be made from the stable
most possible CT,
is the
So this major product
 Addition
Polymers
formed when the double
bond in alkenes open up
and allow them to
join
together
-

eg. polye made up ethere

of
* H monomers
- -
cc
=

-
/ 1 H H H H H H
H
11 l
He -
H -> - - -
- -
-
k-
cC
=

H
-
H / - ↓
-c c =
H

-- H
H -
-
↓
↓ bond
MUST

fi-)
4
He -
c c -
=

R
--H
H

I
number of
units
repeating
polymersarentbiodegradable
any
scientists main
are
the
processed
new biodegradable polymers
legfrom starch ect)
①
landfill
↳> when too difficultto ~- materials wait
run
separate out
Out

② combustion V-CO2 produced from

↳ for energy production decomposition
is the
showever toxic gasses like Same (O2 taken in
be neutralised
Hcl must
with a base) by the
original plant
X much expensive
③ organic feedstock more
-

↳ melted remoulded or broken

+

X- need specific conditions

down into monomers to make to decompose
new plasties and other
organic (still have to be
chemicals
separated)
 Alcohols
Cntant, OH

-
OH

primary,
~
o

ary2" r3

H R
I

12
R C -OH - -on
R
-

- -

or
it R
1alkyl group S 2 alkyl groups 13 alkyl groups
on same carbon same carbon same carbon
on on
as OH) as OH) as OH)

-ly
polar
also
can form
HH H H bonds with

-
I I Iss each other

*
-

H -
c -
C -
C -

0 -

H not
-
very volatile
I don'tevaporate
i
it it
↳ can
form H
-
easily)
spropan-1-017 ands with love pairs
on
oxygen atans in
water

8,8t -

...5
-
-

!
+
15
- xgt
5
11 St
water
H
bonding soluble in

HOWEVER:

larger chain
means most

of molecule non-polar so
is

forms fewer H bonds and is

less soluble
 Reactions of
Alcohols
->
mechanism not required
substitution Reactions
-
halide ions

(catalyst)
+

R- &+Nax
-> R -
x +
Nat + H20

OH is replaced by a
haloger

eg.

-- -
1
12504 -
+
Naci H
-
-

Xat
- -
-

-> +
+

H2a
dr i it
I
it ci
I
can

dissociate
to form OH
and Ilions
/give back to
catalyst)

mechanism not required

Reaction
-nation

- (catalyst) Rem
+

H
n -
-

R -
Heat
R
-
c c =

2 + H20

H H
eg. H H r H 1

-
+

d- I
I *
+ -
-
- -
-
HH
-> c -
c c-
= + 20
Heat &I
or it it i
↳ OH and H
I
leaves c's
climinated to
water to form double
form
bond
Products depend
on it is removed
what
 oxidation of
Alcohols
-stion
↳ type of oxidation reaction
CHOH +60 -
H20
Products complete
of
combustion

can alsobeexidisede
-
acidified
-
( H2S04)
+

Primary Alcohols form aldehydes and then acids

carboxylic
↓ ↓
carbonyl group
cr
0

11 at R
of
end
-

R -

C -
H

COOH
<Propanal) group
at
end of
(H0) chain

spropanoic acid)
Secondary Alcohols form ketones

I
0 in
17
carbonyl group
middle of chain
R -
C -
R
Spropanone)

won'toxidise
Tertiary Alcohols (apartfrom combustion)
 oxidation of
mary Alcohols
to
controlling conditions
partial oxidation aldehydes controls how far the
alcohol is oxidised
H H
I I
H - -
-

0H (0)
+ - - -

H
+
H20
i
↓ i ↳
distil immediatley
to
getaldehyde as

product (so itdoesnt

further oxidise to

carboxylic acid)

+ 8H-3CzH40+2c + H2
3 CHOH +

[0] crbt=orange
mechanism not
cr3+=
green
oxidizing agent required
/So is reduced)

Cr2+
educate
-
H20

↓ anes 6
a total 6e-
fram this to
for happen
3 ethanol
molecules, A
8 from acid come from
the alcohol

HH I-bands break
11
3H -
C c - -
0 -

H -
6H++6e

it leaveother
see
I
H
-

reduce

full oxidation to
carboxylic acid Cr6t

-
1 , I -
H -

C -
C I [0] -> H -
C -
C
-
8H
-
H
I
I 1

aldehyde carboxylic acid

-dary
oxidation to ketones

- -
-
[o]n
+ -
--- H20
+

i H
I
it
I
H H
 Haloalkanes and
Nucleophilic substitution
-Molecules
halogens are much more

electronegative than carbon

cc,6-
-

↳electron deficient
c can be attacked

by
nucleophile
electron rich
species
eg.: NH3,:H

-illie
substitution
Example
drolysing
of
nucleophile attacks asand the nabalkane
takes
halogens place water
or-cons
compound now has a new

functional group

1H
I
netrolysian H1-
1st-g-
r
4
1 - +
-
-
-
-
0 +

it
E
↓

OH nucleophile
can come from
reaction with
alkali for slower reaction
Hydrolysis
with c-x
is faster
bonds -With or from water
with a lower molecules)
enthalpy
F
Cl Br I
->

bond enthalpy decreasing

rate of
.
hydrolysis
increasing
 Environmental
concerns

-our
carb
se

Rit
03 -
RO +02

haloalkanes with all Ro 0

+
-> R' O2
+

It's replaced

Cl ↳ general equation
a -

! -
c
destruction
for
of 03
=
only cl, F, C
were used in lots of
products lect.aerosol cans)

Li ↳
HOWEVER
destroying the
they
ozone
were

layer

02 -x0 +
0

free radicals
-
->

0 02 3
-
+

ozone
can happen with
other radicals too
leg. No
-
CFC's can also be
broken into radicals

↳ eg. CF2Ck *, CF2C1.

--

+
attack Os
can L happens
molecules and c. again
turn them into Oz

C10o +
cio
0 ->
0z + C

Cl acts as

a
catalyst Cozone layer is destroyed)
 IR Spectroscopy
Spectroscopy
-
distinctive peaks
can help
identify
Differentbonds absorb functional groups
differentamounts ofIR
radiation

↳ data sheetin exam

provideswhat frequencies
radiation each
of bond
absorbs

C- H 3000
-
2850

c - c 1600
c -
0 1000 -

1300

0 -
H3230-3550

-am
of ethanol

Enrich
i

300500dwaven't100,000
I
2o so

c -
0

H H
fingerprint
11
H
region
H - C -
C -
0 -

it it
 Mass Spectroscopy
mass spectra
for molecules is
differentto
elements!
->
differentfragments
are produced
when ionised, molecule
can be splitup:

CH3CHzCH,CHz CH3
*
-
F

or here

I
E

possible fragments: 1 Ru)

-

CH3/CH2CHzCHCHs r CH/CHzCHzCHaCHs
·

(57) (15)
CHCHz/CH2CHzCHz CHzCH2 /CH2CHzCH3
·

(43) (29)

CHCHzCHzCHzCHg
(T2)

detected by machine!
only cons

43
base peak
->
-

(mostabundant/stable,
so used for comparison)

57 m peak
24 ~ Imass of
pentane)
15 72