aurorajmz

Chemistry Class
Suiza-Francia 2015

ORGANIC
CHEMISTRY

ORGANIC

Verenice
Aurora Jimenez

CHEMISTRY

Organic Chemistry is the study of the compounds that contain

carbon and hydrogen.

aurorajmz

Chemistry Class
Suiza-Francia 2015

Group 4
Configuration 1s2 2s2 2p2
Science Electrons up to 4 single
bonds
Carbon atoms have four
attachments and bond
angles. They have a
tetrahedral shape

*Concatenation: Chain making

Definitions of Organic and Inorganic
19th
Century
Organic:
Substance that comes
from an organism

Toda
y
Organic:
Substances that
contains carbon and
hydrogen

Inorganic
Inorganic
Substance that comes Everything that doesnt
from an organism
contain carbon and
hydrogen

Frederick Whler 1828

First person to make an organic substance out of inorganic
compounds
Synthetized urea
Representation of elements for organic
molecules
4 bonds
Carbon

Hydrogen

1 bond

aurorajmz

Chemistry Class
Suiza-Francia 2015

Oxygen

2 bonds

Nitrogen

3 bonds

Phosphorus

Sulfur

Halogens (X)

3 bonds
2 bonds
1 bond

How to draw organic compounds

General

C2H6

Expanded

Condensed

CH3 CH3

Skeletal

Possible forms of organic compounds

Linear

aurorajmz

Chemistry Class
Suiza-Francia 2015

Branched

Cyclic

(Benzen
e)

Aromatic

Types of molecules

Saturated

Unsaturat
ed

Only
single
bonds

Double
and triple
bonds

Functional groups
o They help predict how an organic molecule is going to react
o Repetitions of small parts that remain the same
o Every organic chemical reaction happens only where the
functional group is located
o Consistent properties

aurorajmz

Chemistry Class
Suiza-Francia 2015

Organic compounds are organized in families

Each family is characterized by a specific functional group
Ex.

Functional
group

Family

Hydroxyl

Alcohol

-OH

OH

aurorajmz

Chemistry Class
Suiza-Francia 2015

Types of functional groups

Hydrocarbo

Saturated
Single bonds

Alkane
s

Cycloalkan
es

Aromati

Compounds that
contain Benzene

Thiol

R SH
Thiol group

Unsaturated
Double & triple
bonds

Alkyne
s

Alkene
s

Alcohol

R1 OH
Hydroxyl group

Ethe

R1 O R 2
Oxygen

aurorajmz

Chemistry Class
Suiza-Francia 2015

Aldehyde

Ketone

R COH

R1 CO R2

Carbonyl with H

Carboxylic

Carbonyl with
Chain

Ester

R COOH

R1 COO R2

Carbonyl with
hydroxyl

Carbonyl with O

Amine

Amide

R NH2

R CO NH2

Amino group

Carbonyl with
amino

aurorajmz

Chemistry Class
Suiza-Francia 2015

ALKANES
o Simplest of all hydrocarbons
o Single bonds
o Can have conformations (can have different forms)

1) Meth CH4
2) Eth
C2H6
3) Prop C3H8
4) But
C4H10
5) Pent C5H12
6) Hex C6H14
7) Hept C7H16
8) Oct C8H18
9) Non C9H20
10)
Deca
C10H22

ane

CnH2n+
2

Alkanes with substituents

1)
2)
3)
4)
5)

Choose biggest chain

Name biggest branch
Add name of last branch (yl termination)
Add number of carbons the branch is located

4
2

2
1

1
3

Propan
e

Methyl
Propane

2
1

2-Methyl Propane

aurorajmz

Chemistry Class
Suiza-Francia 2015

Alkanes like rings

o Cyclo +

ane

Ex.

Cyclohexane
C6H14
Alkanes same branch types and halogens

o Use prefixes

Branches

Di

Tri

Tetra

Penta

Hexa

Hepta

Octa

Nona

10

Deca

Fluoro

Cl

Chloro

Br

Bromo

Iodo

Halogens

aurorajmz

Chemistry Class
Suiza-Francia 2015

Alkane Reactions

Alkane Combustion

General
form
Alkane +
O2

Alkane Halogenation

CO2 + H2O +
energy

Skeletal
form

2Alkane +
X2

U
V

2Alkane - X +
H2

ALKENES & ALKYNES

aurorajmz

Chemistry Class
Suiza-Francia 2015

o Double bonds between

carbons
o Angle of 120 between
each carbon
o Not longer tetrahedral
o
o
o
o
o
1) Meth
o
2) Eth
o
3) Prop
o
4) But
o
5) Pent
o
6) Hex
o
7) Hept
o
8) Oct
o
9) Non
o
10)
D
o
eca
o
o
o
Alkenes with 1 3
carbons

o Triple bonds between

carbons
o Angle of 180 between
each carbon
o

ene

CnH2n

yne

CnH2n-2

Alkynes with 1 3
carbons

o o
o
o The chain finishes with ene or yne
o
o
o Ex.
o
o
o

Propene

Alkenes with 4 + carbons

Propyne
Alkynes with 4 + carbons

o
o Name the carbon where the double bond is located
o
o
o
o
o

Ex.

aurorajmz

Chemistry Class
Suiza-Francia 2015

o
o

2-Pentene

2-Pentyne

o
o
Alkenes with substituents

Alkynes with substituents

o o
o ONE double/triple bond
o Start counting where the double bond is closest
o
o Ex.
B
B
o
2
r
2
r
o
o
o
1
o
1
o
4-Bromo 5-Methyl 2Hexene
4Bromo 5-Methyl 2-Hexyne
o
o
o TWO or + double/triple bonds
o Treat the bonds as branches (use prefixes)
o Finish name with ane
o
4
o
Ex.
2
2
4
o
o
1
o
3
3
1
o
o
1,3 diene pentane
1,3 diyne
pentane
Alkenes like rings

Alkynes like rings

o
o
o
o

o
o
o
o
o

o One double/triple bond

o No need to number
o
Ex.

aurorajmz

Chemistry Class
Suiza-Francia 2015

o
Cyclobutene
Cyclobutyne

o
o

o With substituent
o The bond will be 1-2 and then counted towards the substituent
o
o
Ex.
1
1
o
o
2
o
3
3
2
o
o
Cis/Trans Isomers
o
o Same name but different conformation (form)
o
o
o
o
o
o
o
o
o
Addition Reaction
o
o

o
o
o
o

Alken
e

CIS

Eliminate double or
triple bonds
o
o

o
o
o
Alkyn
e

o
o
o Hydrogenati
on

Cataly
st
+ n (Binary

Alkan
e

molecule)
*n = extra bonds to
eliminate

+ n (H2)
o

TRANS

Pt/Ni/P
d

aurorajmz

Chemistry Class
Suiza-Francia 2015

o
o
o Halogenatio
n

+ n (X2)
o

o
o
o Hydrohaloge
nation

+n
(HX)
o

o
o
o
o

+ n (H2O)

H
+

o Aromatic

o
o
o
o Discovered by Michael Faraday in 1825
o Benzene > Consists in C6H6
o
o Cloud of electrons that move in the hydrogens, like a metal.
o
o
o
Aromatic types
o
o
o
o
o
CH3
NH2
OH
OH
o
o
o
o

aurorajmz

Chemistry Class
Suiza-Francia 2015

o
o

Toluene
Aniline
Cresol (Methylbenzene)
(Hydroxyl benzene)

Phenol
(Amino benzene)

o
o
o
o
o

Aromatic Naming

o
o
3 or more carbon chain
o The benzene becomes a branch
o
o

1
o
Ex.
o
butane
o
o
o
o
o
With 2 substituents
o
o 1,2 = ortho = o
o
B
o
Ex.
r
o
1
2
B
o
r
o
o
o

2-phenyl

O dibromo
benzene

o
o
o 1,3 = meta = m
o
o
o
o
o
o
o
o
o
o

Ex.

B
r1

M dibromo
benzene

2
3

B
r

o 1,4 = para = p
o

B
r

aurorajmz

Chemistry Class
Suiza-Francia 2015

o
o
o
o
o
o
o
o
o
o
o
o
o

Ex.
1

P dibromo
benzene

3
4
B
r
With 3 or more substituents
o Choose where to start

o
o
o
o Ex.
o
o
o
o
o
o

M-Iodo 4-chloro 5-ethyl phenol

O-Chloro 5-chloro 3,6- diethyl 4-methyl

toluene

Mirror = doesnt
matter where
you start
counting

2,6- dichloro 5-ethyl 4-methyl

m-cresol

aurorajmz

Chemistry Class
Suiza-Francia 2015

o Alcohols
o
o

Alcohols

-OH

Carbon
Chain

o
o
o
o
o
o
o

Naming Alcohols
o
o
o

o Replace the e of ane with an ol

o
o
Ex.
o
o
Methan
Methanol
o
e
o
o
o
o
Alcohols with 2 or + carbons
o
o
o
o
o
o Put the number where the OH is located
o
o
o
o
o
o
o
o
o

OH

Ex.

2
1

4
OH

aurorajmz

Chemistry Class
Suiza-Francia 2015

o
o
o
o
o
o
o
o

Alcohols with 2 or + -OH

o
o
o The OHs become branches
o
o

OH

o
o

OH
6

o
o

o
o

o
o

1
OH

2,3,4 trihydroxy
hexane

o
o

Alcohols like rings

o
o
o
o
o
o
o

o One hydroxyl
Ex.
Cyclopentan
ol

o 2 or more hydroxyls
o As branches
o Finishes with Cyclo
o
o
o

Ex.

OH

ane

aurorajmz

Chemistry Class
Suiza-Francia 2015

o
o

1,3 dihydroxy
cyclopentane
OH

o
o
o

Classification of alcohols

o
o Primary

OH

o
o Secondary

OH

o
o Tertiary

OH

o
o Dehydration

o Oxidations

o
Alcoho
l

1ry
Alcohol
2ry
Alcohol

Alcohol Reactions

H
+

Alken
e

o
Aldehyd
e

o
x
o
x

+
H2O

o
x

Ketone

Carboxylic
acid

aurorajmz

Chemistry Class
Suiza-Francia 2015

3ry
Alcohol

o
x

Cannot be oxidized

o Phenols
o
o
o
o

-OH

Phenols

Benzene

o
o
o

Naming phenols

o Same as naming Aromatics

o
o
o
o
o
o

OH

Ex.
m-Bromo phenol

o
o

B
r

o
o
o

m-Iodo 4-chloro 5-ethyl phenol

aurorajmz

Chemistry Class
Suiza-Francia 2015

o
o
o
o

o Thiols
o
o
o Sulfhydryl group (SH) attached to a chain
o Not pleasant odor
o
o
o
o

Naming Thiols

o
o Add the termination thiol at the end
o
o
2 or more SH
o
Use prefixes
o
o
Ex.
S
o
H
o
o
o
S
S
o
H
H
o
o
o
o
o
o
Thiol Reactions
o
o O
o

o Oxidati
on

3 hexanothiol

2,4 dithiol 3 heptene

CH3 S S
CH3

CH3 SH H + H S
CH3
S
H

o
S
H

SS

+
H2O

+
H2O

aurorajmz

Chemistry Class
Suiza-Francia 2015

o Ethers
o
o
o

R1 O R2

o
o
o

o
o
o

Naming Ethers

o
1) Take into consideration the shortest chain and name it
(always in the start)
o
o
o
o
o

Methoxy
O
2) Change the termination ane to oxy
3) Name the next chain normally

o
o
o
o
o
o

Butane
O
4) Indicate where the o is bonded in the largest chain
o
o

o
o
o

1-Methoxy
Butane
o
o
o
o
o
o
o
o
o
o
o

Ethers like rings

aurorajmz

Chemistry Class
Suiza-Francia 2015

o
o
oxy

o Cyclo +
o
o
o
o
o
o
o
o

Ex.

2 - (2-ene cycloproxy) 2butanol

o
o

o
o
o

OH
o
o
o
o

Ethers like aromatics

o
o

o
o Use the same rules as aromatics
o Ortho, Meta, Para
o Benzene + _______ = ________
o
o
o
o
o
o
o
o

Ex.
O
O Methoxy
toluene

o
o
o
o
o
o
o
When Benzene is the smallest chain
o
o Use it as branch Phenyl with termination oxy
o
o
o

aurorajmz

Chemistry Class
Suiza-Francia 2015

o
o
o
o
o
o
o

1- Phenoxy
pentane
o
When Benzene is the largest chain
o
o Finish with
Benzene

o
o
o
o
o
o
o
o
o

1- Ethoxy
Benzene

Ether Reactions

o
o

o Dehydration

o Hydrolysis

o
2Alcohol
s
Ethe
r

H
+

+
H2O

Ethe
r
H
+

2Alcohol
s

o
o Aldehydes
o
o Presence of a carbonyl group (-COH)
o Polar organic molecule
o
o
o
Aldehydes representation
o

+
H2O

aurorajmz

Chemistry Class
Suiza-Francia 2015

o
O
o Expanded
II
C

o Condensed

R1

o
o

R1 CHO

o
o
o
o
o

o Skeletal
o
o
o

O
II
O
II

o
o
Naming Aldehydes

o
o
o

o
o Change the ane for anal
o
O
II

Butan
e

Butan
al

Aldehydes like aromatics

o
o Use Ortho, Meta & Para
o
o
o
O H
o
II l
o
o
o
o
o
o
o
o
o
o
o
o
o
o
o
o
o
o
o
o
o
o
o
o
o
o
o
o
o

o
o
o

Benzaldehyde

Ke
tones

o
o
o Always 3 carbons or more

o
o
o
o Expanded

o
o
o
o

o Condensed

o Skeletal

o
o
o
o
o

Ketones representation

R1 CO
R2

o
o

o
o
o
o
Naming Ketones

O
II
C
R1
R2

o
o

o
o Replace the ane to anone
o
o
Ex.
o
o
o
o
o
o
Butan
e

Ketone linear with one carbonyl

O
II
O
II
o
o
o

o Specify where the carbonyl is located

o
o
Ex.
O
o
II
o
o
o
o
Ketone cyclic with one carbonyl

Butanon
e

2Pentanone
o

o
o
o Dont have to specify where your carbonyl is
o
o
o
O
o
II
o
o
Cyclohexanon
o
e
o
o
o
o
o
o
o
o
o
o
o
o
o
o
o
o
o
Reactions Aldehydes & Ketones

o
o
o

o
o Reduc
tion
o

o
o

Aldehyde
Ketone

+ H2/NaBH

Pt/Ni

+ H2/NaBH

Pt/Ni

1ry
Alcohol
2ry
Alcohol

o
o Oxida
tion
o

o
o
o
o
o
o
o
o
o
o
o
o
o
o

Aldehyde

o
x

Ketone

o
x

Carboxylic Acid

Cannot be oxidized

o Hemiacetals / Acetals
o
o 1 or 2 molecules of an alcohol to the carbonyl group
o
o
o
Aldehyde
o Hemi
aceta
l

H+

+
Ketone

Alcoho
l

Brakes double bond with O and splits it in two new

bonds

o
o Acet
al
o
o

Hemiacetal

Hemiacetal

Alcoho
l

H+

Aceta
l

+
H2O

o
o Chiral Molecules
o
o Type of isomer
o Stereoisomer
o
Chirality: when the mirror images cannot be completely
matched (nonsuperimposable)
When stereoisomers cannot be superimposed theyre
enantiomers
o
o
Chiral
o
Carbon
o
o
o
Carbon that is
o
bonded to four
o
different
atoms/groups

Ca
rboxylic Acids

o
o Chain bonded to a carboxyl group (COOH)
o
o
o
Carboxylic Acids representation
o
o
o

o Expanded

o Condensed

o
o

o
o
O
II
C
R1
OH

o
o
o
o
o

o Skeletal

O
II

o
o
o
o
Naming Carboxylic Acids

o Termination anoic acid

o
o
o
o
o
o
Butane

o
o
o
O
R1 COOH
II
OH

Carboxylic acids like aromatics

Butanoic acid

o
o
o

OH

o Ortho, Meta & Para

o
o
o
O
o
II OH
l
o
o
o
o
o

Benzoic Acid

Carboxylic Acid Reactions

o
o
o

o
o Oxidati
on

1ry
Alcohol

o
x

Aldehyd
e

o
x

Carboxylic
acid

Carboxylic
acid

Metal
from
G1

o Neutral
ization

OH

Sal
t

Metal +
from H2O
G1

+
H2O

+ Li
OH
o

o*

Butanoic acid changes to Lithium

Butanoate

o
o

Est
ers

o
o Formed when carboxylic acids reacts with an ester, and water
o
o
o
H+
Este
+
o
Carboxylic
+ Alcoho
r
H2O
o
Acid
l
o
o
o
Naming Esters
o
o
1) Find the branch that comes from the O
o
O
o
Eth
II
o
yl
O

o
o
o
o
2) Name the second one with oate termination
o
o
o
o
o
o
o
o
o
o
o
o
o
o
o
o
o

O
II
O
Butanoat
e
3) The one that comes from the O is the first
Ethyl
Butanoate

o
o
o

Esters like rings

o
o
o
o
o
o

O
II

[Cyclopropyl] 2-Methyl
propanoate

O
Esters like aromatics

o
o
o

o
o
o
o
o
o
o
o
o
Ester Reactions

o
o
o

[1-methyl 2-thiol Pentyl] pBromo benzene

o
o
o Forma
tion
o
o Hydrol
ysis
o Saponi
ficatio
n
o

A
mines

o
o
o NH3 its an amonia
o Nitrogen is bonded to 1, 2 or 3 alkyl or aromatic compounds
o
o
o
o
Naming Amines
o
o
o Change the e of ane to the termination NH
amine
3
o
o
o
o
o
Butane
Butanamine
o
o
o
o 3 or more carbons
o
o Specify where your amonia is located
o
NH
3

o
Ex.
o
2- pentanamine
o
o
o
o 2 or more amonias
o
o Treat them as branches called amine
o
o
Ex.
NH
o
3
2,4 - amine pentane
o
o
o
Amines Classification
NH
o
3
o
o
o Primary

o Amino with
one chain

Butanami
ne

o
o Secondary

o Amino with
two chains

N-ethyl
Butanamine

o
o Tertiary

o Amino with
three chains
N-ethyl N-Cyclopropyl
Butanamine

o
Amines like aromatics

o 1 amine
o Use aniline
o
NH2
o
o
o
o
o

o
o
o

Aniline

o
o With substituents
o Use Ortho, Meta, Para
o
Ex.
NH2
o
Br
o
o .

O-Bromo aniline

o
o
o
o REACTIONS RULE
o

Reactions of Amines

R
o

o Neutraliz
ation

+
H2O

o
o
o
o
o

Ammonium
amine

o 1ry
Amine
2ry
Amine
3ry
Amine
o

+
OH=

R
NH2

+ Aci
d

H
X

H2
O

H2
O

Ammonium
salt

R NH
X-

3+

o
o
o
o

A
mides

o
o Amides come from carboxylic acids
o
o
O
o
II
o
C
o
R1
OH
o
Carboxylic
o
o
o
Preparation of Amides

o
o
o
o
o

O
II
C
NH2
R1
Amid

o
o
o

Preparation of Amides

Carboxyli
c Acid

Ammonia

1ry
Amine
2ry
Amine

1ry
Amine
2ry
Amine
3ry
Amine

o
o
o
o Named by dropping the "oic acid and adding the termination
amide.
o
o
O
II

o
o
o
o
o
o
o

NH2
Butane

Butanamide
o
o
o

Reactions of Amides

o Hydrolysis
o
o

o
A

o
O
II
+ HX
C
R1
NH2
o

o
B

o
o
o
o
o
o
o
o
o
o
o
o
o
o
o
o

Produces carboxylic acid &

ammonium salt

O
II
+ NH4
C
+
R1
OH

+ H2O

+ X

Produces carboxylate salt & amine or

ammonia
o

O
II
+
R1 C NH2

Stron
g
base

O
II
C
R1
O

(Strong

base)

+ NH
3