Organic Chemistry

Chemistry Class aurorajmzSuiza-Francia 2015

ORGANIC CHEMISTRY

Organic Chemistry is the study of the compounds that contain carbon and hydrogen.

ORGANICCHEMISTRY

Verenice Aurora Jimenez


Definitions of Organic and Inorganic

Representation of elements for organic molecules

Carbon

Hydrogen

C Group – 4 Configuration – 1s2 2s2 2p2 Science Electrons – up to 4 single

bondsCarbon atoms have four attachments and bond

angles. They have a tetrahedral shape

Concatenation: Chain making*

Organic:Substance that comes

from an organism

InorganicSubstance that comes

from an organism

19th Century

Today

Organic:Substances that

contains carbon and hydrogen

InorganicEverything that doesn’t

contain carbon and hydrogen

Frederick Wöhler 1828First person to make an organic substance out of inorganic

compoundsSynthetized urea

4 bonds

1 bond


Oxygen

Nitrogen

Phosphorus

Sulfur

Halogens (X)

How to draw organic compounds

General C2H6

Expanded

Condensed

Skeletal

Possible forms of organic compounds

Linear

2 bonds

3 bonds

3 bonds

2 bonds

1 bond

–CH3 CH3


Branched

Cyclic

Aromatic

Types of molecules

Functional groups

o They help predict how an organic molecule is going to reacto Repetitions of small parts that remain the sameo Every organic chemical reaction happens only where the

functional group is locatedo Consistent properties

Saturated Unsaturated

Only single bonds

Double and triple

bonds

(Benzene)


Organic compounds are organized in families Each family is characterized by a specific functional group

Ex.

OH

Functional group

Family

Hydroxyl

-OH

Alcohol


Types of functional groups

Hydrocarbons

SaturatedSingle bonds

UnsaturatedDouble & triple

bonds

Alkanes

Cycloalkanes

Alkenes

Alkynes

Aromatics

Compounds that contain Benzene

Alcohols

R1 – OHHydroxyl group

Thiols

R – SH Thiol group

Ether

R1 – O – R2 Oxygen


Aldehydes

R – COH Carbonyl with H

Ketones

R1 – CO – R2

Carbonyl with Chain

Carboxylic Acid

R – COOHCarbonyl with

hydroxyl

Esters

R1 – COO – R2

Carbonyl with O

Amines

R – NH2 Amino group

Amides

R – CO – NH2 Carbonyl with

amino


ALKANESo Simplest of all hydrocarbons o Single bondso Can have conformations (can have different forms)

1) Choose biggest chain 2) Name biggest branch3) Add name of last branch (“yl” termination)4) Add number of carbons the branch is located5)

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

Propane

Methyl Propane

1

2

3

4

1

2

3

1

2

3

4

2-Methyl Propane


o Cyclo + “ane”

Ex.

Alkanes same branch types and halogens

o Use prefixes

Alkanes like rings

CyclohexaneC6H14

Halogens

Branches

2 Di

3 Tri

4 Tetra

5 Penta

6 Hexa

7 Hepta

8 Octa

9 Nona

10 Deca

F Fluoro

Cl Chloro

Br Bromo

I Iodo


Alkane CombustionGeneral

form

Alkane HalogenationSkeletal

form

ALKENES & ALKYNES

Alkane + O2

UV

CO2 + H2O + energy

2Alkane + X2

2Alkane - X + H2

Alkane Reactions


o Double bonds between carbons

o Angle of 120 between each carbon

o Not longer tetrahedral

o Triple bonds between carbons

o Angle of 180 between each carbon

The chain finishes with “ene” or “yne”

Ex.

Propene Propyne

Name the carbon where the double bond is located

Ex.

2-Pentene 2-Pentyne

1) Meth 2) Eth 3) Prop 4) But 5) Pent 6) Hex 7) Hept 8) Oct 9) Non 10) D

eca

“yne”

Alkenes with 1 – 3 carbons

Alkenes with 4 – + carbons

“ene”

Alkynes with 1 – 3 carbons

Alkynes with 4 – + carbons

CnH2n

CnH2n-2


ONE double/triple bondStart counting where the double bond is closest

Ex.

4-Bromo 5-Methyl 2-Hexene 4-Bromo 5-Methyl 2-Hexyne

TWO or + double/triple bondsTreat the bonds as branches (use prefixes)

Finish name with “ane”

Ex.

1,3 – diene pentane 1,3 – diyne pentane

One double/triple bondNo need to number

Ex.

Cyclobutene Cyclobutyne

Alkenes with substituents

Br

1

Alkenes like rings

4

Alkynes with substituents

2Br

1

2

2

13

4

3 1

2

Alkynes like rings


With substituentThe bond will be 1-2 and then counted towards the substituent

Ex.

o Same name but different conformation (form)

Eliminate double or triple bonds

Hydrogenation

1 1

22

3 3

Addition Reaction

Alkene

Alkyne

+ n (Binary molecule)

Catalyst Al

kane

*n = extra bonds to eliminate

+ n (H2)Pt/Ni/Pd

Cis/Trans Isomers

CIS TRANS


Halogenation

Hydrohalogenation

Hydration

Aromatico Discovered by Michael Faraday in 1825 o Benzene > Consists in C6H6

“Cloud of electrons that move in the hydrogens, like a metal.”

Toluene Aniline Phenol Cresol (Methylbenzene) (Amino benzene) (Hydroxyl benzene)

Aromatic types

OHNH2CH3 OH

+ n (HX)

+ n (X2)

+ n (H2O)H+


3 or more carbon chaino The benzene becomes a branch

Ex. 2-phenyl

butane

With 2 substituents

o 1,2 = ortho = “o”

Ex.

o 1,3 = meta = “m”

Ex.

o 1,4 = para = “p”

Ex.

Aromatic Naming

12

34

Br

Br

Br

Br

Br

Br

1 2

21

3

12

3

4

O – dibromo benzene

M – dibromo benzene

P – dibromo benzene


With 3 or more substituents

o Choose where to start

Ex.

M-Iodo 4-chloro 5-ethyl phenol

Mirror = doesn’t matter where

you start counting

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

2,6- dichloro 5-ethyl 4-methyl m-cresol


Alcohols

o Replace the “e” of “ane” with an “ol”

Ex.

o Put the number where the –OH is located

Ex.

-OHAlcohols Carbon Chain

Naming Alcohols

Methane

Methanol

Alcohols with 2 or + carbons

OH

1

2

3

OH

123

4


o The –OH’s become branches

o One hydroxyl Ex.

o 2 or more hydroxyls o As brancheso Finishes with Cyclo ane

Ex.

Alcohols with 2 or + -OH

OH OH

OH

1

2 3 4 5

6

2,3,4 – trihydroxy hexane

Alcohols like rings

Cyclopentanol

OH


Primary

Secondary

Tertiary

Dehydration

Oxidations

OH

1,3 – dihydroxy cyclopentane

Classification of alcohols

Alcohol Reactions

OH

OH

OH

Alcohol

Alkene

+ H2O

H+

1ry Alcohol

Aldehyde

Carboxylic acid

ox

2ry Alcohol

ox

ox

Ketone


Cannot be oxidized

Phenols

o Same as naming Aromatics

Ex.

-OHPhenols Benzene

Naming phenols

OHm-Bromo phenol

Br

m-Iodo 4-chloro 5-ethyl phenol

3ry Alcohol

ox


Thiolso Sulfhydryl group (SH) attached to a chaino Not pleasant odor

o Add the termination “thiol” at the end

2 or more SH

Use prefixes

Ex.

Oxidation

Naming Thiols

SH 3 – hexanothiol

2,4 – dithiol 3 - heptene

SH

SH

CH3 – SH – H + H – S – CH3

CH3 – S – S – CH3

+ H2O

SH + S

H

O

O + H2O

S-S

Thiol Reactions


Ethers

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

2) Change the termination “ane” to “oxy” 3) Name the next chain normally

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

Naming Ethers

R1 – O – R2

OMethoxy

O

Butane

1-Methoxy Butane

Ethers like rings


o Cyclo + “oxy”

Ex.

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

Ex.

When Benzene is the smallest chain

o Use it as branch “Phenyl” with termination “oxy”

Ethers like aromatics

O

OH

2 - (2-ene cycloproxy) 2-butanol

O

O – Methoxy toluene

O


When Benzene is the largest chain

o Finish with “Benzene”

Dehydration

Hydrolysis

Aldehydes

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

1- Phenoxy pentane

O

1- Ethoxy Benzene

2Alcohols

Ether

+ H2O

Ether

H+

Ether Reactions

+ H2O

H+ 2Alcohol

s

Aldehydes representation


Expanded

Condensed

Skeletal

o Change the “ane” for “anal”

O IIC R1 – – H

R1 – CHO

O II

O II

H

Naming Aldehydes

O II

Butane

Butanal


o Use Ortho, Meta & Para

Ketoneso Always 3 carbons or more

O II

H l

Benzaldehyde

Aldehydes like aromatics


o Replace the “ane” to “anone”

Ex.

o Specify where the carbonyl is located

Ex.

R1 – – R2

Ketones representation

O IIC

O II

Naming Ketones

Butane

Butanone

O II

O II

2-Pentanone

Ketone linear with one carbonyl

Ketone cyclic with one carbonyl

Expanded

Condensed

Skeletal

R1 – CO – R2


o Don’t have to specify where your carbonyl is

O II

Cyclohexanone

Reactions Aldehydes & Ketones

Aldehyde

+ H2/NaBH4

Ketone

+ H2/NaBH4

1ry Alcohol

2ry Alcohol

Pt/Ni

Pt/Ni

Reduction


Hemiacetals / Acetals

o 1 or 2 molecules of an alcohol to the carbonyl group

Hemiacetal

Acetal

Aldehydeox Carboxylic Acid

Ketone ox

Cannot be oxidized

Ketone

Aldehyde

+ Alcohol

Brakes double bond with O and splits it in two new bonds

H+

Hemiacetal

+ Alcohol

H+

AcetalHemiacetal + H2O

Oxidation


Chiral Molecules

o Type of isomero Stereoisomer

Chirality: when the mirror images cannot be completely matched (nonsuperimposable)

When stereoisomers cannot be superimposed they’re enantiomers

Carboxylic Acidso Chain bonded to a carboxyl group (COOH)

Chiral Carbon

Carbon that is bonded to four

different atoms/groups

Carboxylic Acids representation


o Termination “anoic acid”

o Ortho, Meta & Para

R1 – COOH

OH

Naming Carboxylic Acids

O II

OH

Butane Butanoic acid

Carboxylic acids like aromatics

O II

OH l

Benzoic Acid

Carboxylic Acid Reactions

Expanded

Condensed

Skeletal

R1 – – OH

O IIC

O II


Oxidation

Neutralization

*

Esterso Formed when carboxylic acids reacts with an ester, and water

1) Find the branch that comes from the O

1ry Alcohol

Aldehyde

Carboxylic acid

ox

ox

Carboxylic acid

+Metal from G1

OH Salt

+ H2O

Metal from G1

+ Li OH

+ H2O

Butanoic acid changes to Lithium Butan oate

*

Carboxylic Acid

+ Alcohol

H+

Ester

+ H2O

Naming Esters

O II Eth

yl


2) Name the second one with “oate” termination

3) The one that comes from the O is the first

O

O II

O

Butanoate

Ethyl Butanoate

Esters like rings

O II

[Cyclopropyl] 2-Methyl propanoate

Esters like aromatics

O

[1-methyl 2-thiol Pentyl] p-Bromo benzene

Ester Reactions


Formation

Hydrolysis

Saponification

Amineso NH3 it’s an “amonia”o Nitrogen is bonded to 1, 2 or 3 alkyl or aromatic compounds

o Change the “e” of “ane” to the termination “amine”

3 or more carbons

o Specify where your amonia is located

Ex.

Naming Amines

Butane Butanamine

NH3 2- pentanamine

NH3


2 or more amonias

o Treat them as branches called “amine” Ex.

PrimaryAmino with one

chain

SecondaryAmino with two

chains

TertiaryAmino with three

chains

1 amineo Use aniline

NH3

NH3

2,4 - amine pentane

Amines Classification

N-ethyl Butanamine

N-ethyl N-Cyclopropyl Butanamine

Butanamine

Amines like aromatics

NH2

Aniline


With substituentso Use Ortho, Meta, Para

Ex.

.

REACTIONS RULE

Neutralization

Reactions of Amines

NH2

Br O-Bromo aniline

R – NH2

+ H2O

R – NH3

+

+ OH=

Ammonium amine

1ry Amine

+ Acid

H2O Ammonium

salt

R – NH2

+ HX

H2O

R – NH 3+

X -

2ry Amine3ry Amine


Amideso Amides come from carboxylic acids

o Named by dropping the "oic acid” and adding the termination “amide”.

R1 – – OH

O IIC R1 – – NH2

O IIC

Carboxylic Amid

Preparation of Amides

Butane Butanamide

OII

NH2

Preparation of Amides

1ry Amine

3ry Amine

2ry Amine

Carboxylic Acid

+ Ammonia

+ 1ry Amine

+ 2ry Amine


Hydrolysis

Acid

Base

Reactions of Amides

Produces – carboxylic acid & ammonium salt

R1 – – NH2

O IIC

+ HX +H2OR1 – – OH

O IIC

N

H4+

+ + X -

Produces – carboxylate salt & amine or ammonia

R1 – – NH2

O IIC +

Strong

base

R1 – – O –

O IIC +(Strong

base) +NH3

Organic Chemistry

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