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Organic Chemistry

Organic Chemistry

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Published by: Lindy Han on May 15, 2011
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05/17/2014

ORGANIC CHEMISTRY

Notes
FUELS AND CRUDE OIL
Hydrocarbons: compounds made up of only carbon and hydrogen molecules. Petroleum A mixture of various hydrocarbons These hydrocarbons are separated by fractional distillation Petroleum gas B.P.: < 25 C

Petrol (gasoline) B.P.: 35-75 C Naphtha B.P.: 70-170 C Kerosene (Paraffin) B.P.: 170-250 C Diesel B.P.: 250-340 C Petroleum Lubricating oil B.P.: 350-500 C

Bitumen B.P.: > 500 C

Highest boiling point

Highest number of C atoms

More C atoms larger compound higher boiling point

© Han, 2011. All rights reserved.

ALKANES, ALKENES
Homologous series: A group of organic compounds with a general formula and similar chemical properties.

Alkanes: CnH2n+2.

CH4 Methane H H C H C2H6 Ethane H H C H C3H8 Propane H H C H C4H10 Butane H H C H C5H12 Pentane H H C H H C H H C H H C H H C H H Highest b.p., density, viscosity H C H H C H H C H H H C H H C H H H C H H H

Most flammable

© Han, 2011. All rights reserved.

Because alkanes contain only single bonds, they are saturated compounds.

P HYSICAL PROPERTIES : 
More C atoms larger mass stronger intermolecular forces Boiling points of alkanes increase down the series. Larger alkanes exist in liquid and solid forms. Density and viscosity also increase down the series. Solids and liquids are less flammable than gases. Flammability decreases down the series. Soluble in organic solvents Insoluble in water   

A LKANE REACTIONS
Cracking: One large compound to two or more smaller compounds C6H14 --------> C4H10 (Hexane) (Butane) + C2H4 (Ethene)

H H C H

H C H

H C H

H C H

H C H

H C H H H

H C H

H C H

H C H

H C H

H H + C H

H C H

Combustion: C4H10 + O2 4 CO2 + 5 H2O

© Han, 2011. All rights reserved.

Substitution: 2 C2H4 + Cl2 H H C H H H C H
UV light

2 C2H3Cl + H2

H C H H C H H
swap

H H
swap

H C H H C H Cl Cl + H H

H Cl Cl
UV light

C H H

+

H

C H

© Han, 2011. All rights reserved.

Alkenes: CnH2n.

CH2 Methene

Most flammable

H

C

H

C2H4 Ethene H H C H C H

C3H6 Propene H H C H C4H8 Butene H H C H C5H10 Pentene H H C H H C H H C H H C H C H Highest b.p., density, viscosity H C H H C H C H H C H C H

Because alkenes have double bonds C

C , they are unsaturated compounds.

© Han, 2011. All rights reserved.

P HYSICAL PROPERTIES
Same as alkanes

I SOMERISM
Same molecular formula, different structural arrangement

C4H8 Butene H H C H H C H H C H C H

C4H8 Butene H H C H H C H C H C H H

A LKENE REACTIONS
C OMBUSTION : 2 C3H6 + 9 O2 6 CO2 + 6 H2O

A DDITION : breaking a C -

C double bond to add in

a halogen (Cl, Br, I) [HALOGENATION] hydrogen [HYDROGENATION] or H2O [HYDRATION]

© Han, 2011. All rights reserved.

HALOGENATION C2H2 + Br2 (aq) (brown solution) H H C H C H + Br Br H C2H4Br2 (brown solution is decolorized) H C Br H C Br H

HYDROGENATION C2H2 + H2 H H C
200 C Ni catalyst

C2H6 H H C H H

H C H + H H H

C H

HYDRATION C2H2 + H2O (g) (ethane) (steam) H H C H C H + H OH H
300 C, 60atm H3PO4 catalyst

C2H5OH (l) (ethanol) H C H H C OH H

© Han, 2011. All rights reserved.

ALCOHOLS, CARBOXYLIC ACIDS

Alcohols: CnH2n+1OH.

CH3OH Methanol H H C H C2H5OH Ethanol H H C H C3H7OH Propanol H H C H C4H9OH Butanol H H C H C5H11OH - Pentanol H H C H H C H H C H H C H H C H OH Boiling point, density, viscosity H C H H C H H C H OH H C H H C H OH H C H OH OH

Flammability

The

OH functional group is called the hydroxyl group.

© Han, 2011. All rights reserved.

F ERMENTATION
yeast Glucose solution ------------> ethanol + carbon dioxide

The enzymes in yeast work best at 37 C. Above this optimum temperature, fermentation cannot take place.

A LCOHOLIC R EACTIONS
C OMBUSTION C3H7OH + 5 O2 3 CO2 + 4 H2O

O XIDATION Warming alcohols with oxidizing agents to form organic acids and water C2H5OH + [O] [acidified potassium dichromate (VI)] -------------> CH3COOH (aq) + H2O (l)

remove

H H C H
remove

H C H OH +

add

H H C H

O C OH + H O H

[O]

Observation: Acidified potassium dichromate turns from ORANGE to GREEN

© Han, 2011. All rights reserved.

Carboxylic acids: CnH2n+1COOH

HCOOH Methanoic acid O H C OH

Flammability

CH3COOH Ethanoic acid H O H C H C2H5COOH Propanoic acid H H C H H C H O C OH C OH

C3H7COOH Butanoic acid H H C H H C H H C H O C OH

C4H9COOH - Pentanoic acid H H C H H C H H C H H C H O C OH Boiling point, density, viscosity

O The C OH functional group is called the carboxyl group.

© Han, 2011. All rights reserved.

C ARBOXYLIC ACID REACTIONS
T YPICAL ACIDIC REACTIONS With BASES CH3COOH (aq) + NaOH (aq) --------> CH3COONa (aq) + H2O (l) (acid) (base) (salt) (water)

2 CH3COOH (aq) + ZnO (aq) --------> (CH3COO)2Zn (aq) + H2O (l) (acid) (base) (salt) (water)

With METALS 2 CH3COOH (aq) + Mg (s) ------------> (CH3COO)2 Mg (aq) + H2 (g) (acid) (metal) (salt) (hydrogen)

With METAL CARBONATES 2 CH3COOH (aq) + CaCO3 (aq) (acid) (metal carbonate) --------------> (CH3COO)2Ca (aq) + CO2 + H2O (l) (salt) (carbon dioxide) (water)

E STERIFICATION CH3COOH (aq) + C3H7OH (carboxylic acid) (alcohol)
conc. H2SO4

CH3COOC3H5 + H2O (ester) (water) Ester linkage

remove

remove

H H C

O C OH + H O

H C H

H H C C H H

H C H

O C O

H C H

H C H

H C H Water H + H O H

H Ethanoic acid

H H

Propanol

Propyl-Ethanoate

© Han, 2011. All rights reserved.

MACROMOLECULES
molecule + molecule + molecule + molecule + molecule + macromolecule

Plastic is made of macromolecules. Small molecules called monomers are joined together to form a giant molecule called a polymer, through a process called POLYMERIZATION. monomer + monomer + monomer + monomer + monomer + + + + + polymer

There are 2 types of polymerizations: POLYMERIZATION BY ADDITION and POLYMERIZATION BY SUBSTITUTION

A DDITION P OLYMERIZATION
breaking of C=C bonds to join monomers H C H H C H + H C H H C H + H C H H C H more ethene + H C H H C H H C H H C H H C H H C H

ethene

ethene

ethene

polyethene

This equation can also be written as H n C H H C H H C H H C H n

n ethene molecules Another example: H n C H Cl C H

polyethene

H C H

Cl C H n

n Chloro-ethene molecules

polychloroethene
© Han, 2011. All rights reserved.

C ONDENSATION P OLYMERIZATION
Forming polymers by removing water (H2O) molecules

N YLON (P OLYAMIDE )
remove remove

Amide linkage

H N H

H N H +

OH C O

OH C O

H N

H N C O C O + H O H

remove

T ERYLENE (P OLYESTER )

remove

remove

Ester linkage

OH HO OH + C O
remove

OH C O O O C O C O + H O H

© Han, 2011. All rights reserved.

Workout Questions
1. Which of the following statements is true about solid fats and oil? a. Solid fats are saturated fat, oil is unsaturated b. Solid fats are unsaturated, oil is saturated c. Both solid fats and oil are saturated d. Both solid fats and oil are unsaturated 2. Which is a chemical test that can distinguish between vegetable oils and butter? a. Vegetable oils will turn limewater chalky b. Vegetable oils will delocolorize aqueous bromine solution c. Butter will turn red litmus paper blue d. Butter will form hydrogen bubbles with HCl 3. When a hydrocarbon undergoes complete combustion, what are the products formed? a. Carbon and hydrogen b. Carbon, hydrogen and oxygen c. Carbon dioxide, carbon monoxide and water d. Carbon dioxide and water 4. Which substance reacts with propane? a. Acidified potassium dichromate b. Ethanol c. Chlorine d. Water 5. Which physical property of alkenes increases with their relative molecular masses? a. Boiling point b. Electrical conductivity c. pH d. Reactivity 6. Which of the following compounds is most likely to be oxidized to a carboxylic acid? a. C2H6 b. C3H8O c. HCOOH d. C3H6

© Han, 2011. All rights reserved.

7. How do isomers differ? a. They have different empirical formulas b. They have different chemical properties c. They have different structural formulas d. They have different pHs 8. Which of the following liberates a gas that forms a white ppt when bubbled through Ca(OH)2? a. CH3COOC2H5 b. CH3COOH c. C2H5OH d. C2H4 9. Propanol can be manufactured by oxidizing a. Propane b. Propene c. Propanoic acid d. Propyl propanoate 10. How is ethanoic acid different from hydrochloric acid? a. It reacts with alcohols to form esters b. It reacts with copper to form a salt and hydrogen gas c. It neutralizes alkalis d. It reacts with metal carbonates to liberate carbon dioxide 11. Draw 3 possible isomers of butene.

© Han, 2011. All rights reserved.

12. Using two reactants, butyl propanoate is formed. a. Write out the chemical equation, showing the full structural formulae of all reactants and products.

b. What are the physical conditions and/or catalysts required in this process? ________________________________________________________________________

c. What is the name of this process? ________________________________________________________________________ d. Suggest a commercial use for the product formed. ________________________________________________________________________

© Han, 2011. All rights reserved.

13. Nylon and Terylene are examples of polymers. a. State one similarity and one difference in the way they are formed. ________________________________________________________________________ ________________________________________________________________________ b. Illustrate the linkages in Nylon and Terylene. Nylon:

Terylene:

© Han, 2011. All rights reserved.

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