ORGANIC CHEMISTRY

Alphatic compunds

Alkynes

IUPAC name-yne

undergo reactions

Hydration- water reacts with alkyne and produces a organic compound with a hydroxyl group (-OH)

hydrogenation

higher melting/boiling points than alkenes

non polar

unsaturated hydrocarbons

consist of at least 2 carbons bonded together by a triple bond

Alkynes formula CnH2n-2

Cyclivc Alkane: Cyclohexane

Alakanes

formula CnH2n+2

saturated hydrocarbon

soluble in organic solvents

nonpolar

Saturated compounds that cannot undergo further addition reactions, only subsitution reaction

Aromatic Compounds

Formula CnH2n

higher melting/boiling points than alkanes

can undergo addition reaction

hydrogenation -> alcohols

other functional groups C=C

Unsaturated compounds

IUPAC name: -ene

Benzene

Structure

insoluble in water

Higher melting/boiling points than alkynes

Carbon to carbon ring all are the same length

flat 6 carbon ring with a hydrogen atom bond to each carbon atom

Pi bonds

Consists of two p orbitals that overlap above and below a sigma bond. A double bond has one sigma bond and one pi bond

more reactive than sigma bonds

electron geometry

methanes for identical hybrid sp3 are arranged in a tetrahedral to minimize electrostatic repulsion. Which creates sigma bonds

Sp3- single bonds Sp2-double bonds sp triple bonds of carbon

Carbons valence electron can hybridize in three different ways

methane is the smallest hydrocarbon

the other 2 atoms are perpendicular an 2N2 addition reaction

3 atoms bond in the place of the central atom with 120 bond angles

Atoms with five bonds create trigonal bipyramid geometry

Doulbe bonds have a trigonal planar geometry, with bonds angles to 120 and a flat shape

Functional group

Ethers

Ketones

Amine

Alcohol

Aldehydes

Ester

Carbocylic acid

Carboxylic Acids

Molecular Formula

C5H11COOh

hexanoic acid

C4H9COOH

pentanoic acid

C3H7COOH

butanoic acid

C2H5COOH

propanic acid

CH3COOH

ethanoic acid

1 HCOOH

Methanoic acid

General formula CnH2n+1COOH

Reactions with alcohol-esterfication

High melting/boiling points

Polar

Peperation

Forms Nitriles

Will dilute in HCL

Saturated Compounds

Alkanes: Have single bonds between carbon atoms

C10H22

Decane

C9H20

Nonane

C8H18

Octane

C7H16

Heptane

C6H14

Hexane

C5H12

Pentane

C4H10

Butane

C3H8

Propane

C2H6

Ethane

CH4

Unsaturated Compounds

Alkenes: Have 1 double carbon somewhere in the chain

Molecular formula

9 C9H20

Dec-1-ene

8 C8H18

Non-1-ene

7 C7H16

Oct-1-ene

6 C6H14

Hept-1-ene

5 C5H12

Hex-1-ene

4 C5H10

Pent-1-ene

3 C4H8

But-1-ene

2 C3H6

Propene

1 C2H4

CH2: Because of the structure is not stable

General formula: CnH2n

a triple bond= sigma+ two pi bonds

Each Sp hybrid orbitals is involved in a sigma bond formation and the p orbitals forms tow pi bonds

The 2 sp hybrids are at 180 angle

Sp hybridization occurs when a C has 2 attached groups

each Sp2 hybrid orbital involved in a sigma bond formation and the remaining p orbitals from the pi bonds

Sp2 hybridization occurs when a c has 3 attached groups

each Sp3 hybrid orbital is involved in a sigma bond formation

Sp3 hybrid orbital has 25% and 75% p character

Sp3 hybridization occurs when a C has 4 attached groupls

Key to Carbons felxibility

Hydrocarbon Derivatives

Condensation reaction, a carboxylic acid can react with ammonia or a primary or secondary amine to produce an amide

Hydrocarbon chains with a terminal carboxyl group bonded to an amino group

Produces stable bonds

weak bases, more soulble in water

substitution: an organic halogen can react with ammonia to produce amine

higher bp than alkanes, but lower than alcohols and less soluble in water than reactive alcohols

Higher bp and more soluble in water than reactive hydrocarbons

Hydrocarbons with an amino acid, bonded to a carbon chain

increased soulublity, in polar solvents

produce basic solutions

Ketones and Aledehydes

Carbonyl group is polar, but cannot hold H bonds

Lower boiling points and higher

Reactions

Oxidation reactions: involves the addition of oxygen atoms or loss of hydrogen atoms

hydrocarbons containing C=O bonds, in the group chain

Alcohols

Types of Alcohols

Tertiary Alcohol: Hydroxyl group -OH is bonded to a carbon atom that has three alkyl groups, bonded to it

Secondary Alcohol: -OH is bonded to a carbon atom is attached to 2 other carbon atoms

primary alcohols: hydroxyl group -OH is bonded to a carbon at the end of the chain

reactions

Condensation- joining smaller molecules by elimination

Polimerization: - addition-breaking of C=C bonds in smaller alkene compounds

can be reversed by dehydration reaction to produce a alkene and water

can be produced by the hydration reaction of a alkene

esters can produced fro the condensation reaction of alcohols

esterification: alcohol + carboxylic acid ->

combustion: alcohol + oxygen -> carbon dioxide and water

Physical Properties

melting/boiling points higher than alkanes

very flammable

soluble in water

Describing and comparing the physical properties of Aliphatic and Aromatic hydrocarbons ( including what reactions the hydrocarbons go through)

Amides

used to make proteins

properties depend on the amount of H atoms bonded to N and chain length

Amines

Increased solubility in polar solvents

Produces basic solution

Subsitution reaction

Esters

Polar functional group, loses ability to form H+

Relative to the carboxylic acid, melting/boiling point decreases and less soluble in water

Carboxylic acids

properties compared with alkane

high polar function ( H bond)

increase in melting/ boiling points, greater water solubility. produces H ions, acidic

Condensation reaction

Aldehydes and Ketones

Compared to alkanes, higher melting/ boiling point. And great solubility

Reactions with Ethers

condensation reaction ( dehydration)

Organic Ethers

polar molecules

slightly higher boiling point than alkanes, but much lower than alcohols

Soluble in polar and non polar solvents

Subsitiution of Alcohol for Halogen group

More stable carboncation, the more favourable and quicker reaction

Reactions with Alcohols

undergoes complete combustion

Hydration reactions ( addition ) Alkenes -> Alcohols can produce primary, secondary, and tertiary alcohols

Dehydration reactions ( elimination) reaction that involves the removal of H2O

Hydroxyl group

changes the properties of the hydrogen. Greater solublitity in water, higher melting/ boiling point

Organic Alcohols

Can be created by hydration of alkenes and alkynes and others

Organic Halids

are polar, higher boiling point than corresponding hydrocarbon more soluble in polar solvents

Halides

Can be added or subsituted onto hydrocarbons chains

Sigma bonds

The bonds formed in methane between carbon and hydrogen atoms

formed by the head on overlap of two orbitals

Hybridization

subsitution of alcohols for halogen are an SN1 reactions. The easier it is to form, the faster the SN1 reaction will be

Esthers

IUPAC naming: to name a ester, it must be identified what the alcohol is. The ol and yl is added. For the carboxylic acid the -oic acid is dropped and replaced with -oate

Hydrolysis

reflux with acid/base

Base

Not reversible

Alcohol+Sodium salt of COOH

Soluble base,NaOH aq

CH3COOCH2CH3+NaOH->CH3COO-Na+CH3CH2OH

Acid

Reversible

CH3COOC2H5+H2O-><- CH3COOH+CH3CH2OH

Hydrolysis: reverse reaction of esterification by the addition of hydrogen and oxygen

Alcohol+ Carboxylic Acid

First part: Alcohol Second part: Carboxylic acid

C2H5OH+CH3COOH->CH3COOC2H5+H2O

Esterfication

Sweet and fruity smell

Flavourings, perfumes, solvents