Organic Chemistry

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Organic Compounds

• Organic compounds are molecules that contain carbon.

• Carbon is the base of organic compounds for 3 reasons:

1. Carbon forms stronger covalent bonds than most other non-metals

2. Carbon forms more stable molecules than most other non-metals

3. Carbon can form up to 4 bonds at a time, which gives many possibilities for molecules.

Structure of Organic Compounds• Besides carbon, the most common elements in organic compounds are: H, O, N, S, & halogens.

• Organic compounds are held together with covalent bonds.

• Organic compounds must meet the octet rule (S does not break the octet rule)

Hydrocarbons

• Hydrocarbons are the most simple organic compounds

• Hydrocarbons only contain C & H• All other organic compounds are derivatives of

hydrocarbons• Petrochemicals contain hydrocarbons, including:

propane, butane, and octane• Saturated – a compound is termed “saturated” if it has

the maximum hybridization (sp3) at each carbon!

Therefore: no double or triple bonds 

HydrocarbonsC2H6

Alkanes• Single bonded carbons

• Strongest, most stable hydrocarbo

ns

• CnH2n+2

• saturated

C2H4

Alkenes• A double bonded carbon

• Weaker, less

stable hydrocarbons

• CnH2n

• unsaturated

C2H2

Alkynes• A triple

bonded carbon

• Weakest, least stable hydrocarbo

ns

• CnH2n-2

• unsaturated

C6H6

Aromatics

Ring of carbons

with alternating double

and single bonds

C6H12

cycloalkane• ring

• CnH2n

• unsaturated

Simple Organic NomenclaturePrefixes used with organic

compounds1. meth- 6. hex-2. eth- 7. hept-3. prop- 8. oct-4. but- 9. non- 5. pent- 10. dec-

Name the following organic compoundsa. CH4 ___________________

b. C3H8 ___________________

c. C3H6 ___________________

d. C4H10 ___________________

e. C5H8 ___________________

f. C3H4 ___________________

methanepropane

propene

butanepentynepropyne

Suffixes used with organic compounds

-ane = CnH2n+2

-ene = CnH2n

-yne = CnH2n-2

Nomenclature RulesProcedure for naming carbon chains containing branches or substituents (non-straight chain)1)  Find the longest continuous carbon chain in the structure-this determines the root name

2) Any carbon not on this continuous chain is a substituent (appendage)3) Number the main chain starting from the end closest to the first substituent4)  The substituents are still named according to the number of carbons(the suffix for a substituent is –yl instead of –ane)

-CH3 methyl-CH2CH3 ethyl

5) Place all substituent names before the root name in alphabetical order6) The substituent must be numbered to indicate the point of attachment to the main chain7) Group multiple substituents of the same kind together and label di-, tri-, etc.8)  When alphabetizing, the prefixes di-, tri- are ignored9)  With a ring compound the number of carbons in the ring determines the root name with a cyclo- prefix10)  Halogens are named as substituents with an -o suffix

e.g. fluoro-, chloro-, bromo- or iodo-

Isomers - Compounds with the same molecular formula but different structural arrangement therefore a different name.

A. hexaneB.  2-methylpentane

C.  3-methylpentaneD.  2, 2-dimethylbutane 

E.  2,3-dimethylbutane

C6H14

1-Butene

3-Heptyne

Draw & Name the following

C

H

H

H

HC C C

H

H HH

C

H

H

H

HC C C

H

H H

C C C

HHH

H H

C4H8

C7H12

C3H6 or CH3CH=CH2

C4H8 or H2C=CHCH2CH3

CH

H

H

CH

C

H

1-propene

H

H

H

H

H

C C

H

CH

CH

1-Butene

H

Functional Groups

• Functional groups are any atom, group of atoms, or organization of bonds that determine the properties of a molecule.

• Functional groups are the most reactive part of a molecule

• Functional groups directly determine the properties of a molecule

Functional Groupsa. Alcohols: -OH

When carbon is single bounded to an –OH Ex. Propanol

3-pentanol

Add –ol to name

H

H

H

H

C C

H

H

C

H

O••••

H

b. Aldehydes: -C=OH - always on the endExample:

c. Carboxylic Acids: COOHMost common organic acids belong to this group.Example:

pentanal

Add –al to name

Propanoic Acid

Add –oic Acid to name

d. Ketones: -C=O (also called a carbonyl group)

Example:

e. Esters are formed when a carboxylic acid reacts with an alcohol. This reaction is called esterification.

–O-C=OExample:methyl butanoate

Add –oate to name

Smells like pineapple

4 -octanone

Add –one to name

f. Halohydrocarbons: Halogen substituted for a hydrogen

Example:

F

H

Br

F

C C

Cl

F

2-bromo-2-chloro-1,1,1-trifluoroethane.

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Polymers

• Polymers are long carbon chains made of repeating units

• Both natural and synthetic (man-made)

Natural Polymer Examples

•Nucleic Acids• Examples: DNA, RNA

• Carbohydrates• Examples: starches, sugars

• Enzymes (protein catalysts that speed up chemical reactions)

• Example: lactase• Vitamins (naturally in plants & animals)• Insulin (naturally made in your body)

Synthetic Polymer Examples

• Plastics (made from petrochemicals)

• Examples: polystyrene, Styrofoam, polyvinyl chloride (PVC), nylon

• Kevlar (used in ballistic vests and combat helmets)• Pharmaceuticals

• First synthetic pharmaceutical was aspirin