AP Chem Organic Review

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Carbon

Hydrogen
Fluorine
Oxygen
Nitrogen
Alkanes (Paraffin Series): CnH2n+2

 Single bond between carbon atoms

 First member is methane

 Saturated

 Carbons have tetrahedral shape (109.5°)

Ethane

Alkenes (Ethylene Series): CnH2n

 Double bond between carbon atoms

 First member is ethene

 Unsaturated

 Not very reactive due to bond strength except for combustion reactions

 When naming, the DOUBLE BOND is closest to 1 (not any other functional groups)

Ethene

Alkynes (Acetylene Series): CnH2n-2


 First member is ethyne

 A triple bond between carbons

 Unsaturated

Ethyne

Cycloalkanes: CnH2n

 Carbons are as close and compact as possible, but are less stable than the normal alkanes

 Decrease in size of ring = increase in reactivity

Cyclopropane

Aromatics (Benzene series): CnH2n-6

 The three sets of double bonds makes it very stable due to delocalized pi bonds with resonance

structures

Benzene

Methylbenzene =Toluene
1,2-dimethyl benzene Ortho-dimethyl benzene  O-dimethyl benzene

1,3-dimethyl benzene Meta-dimethyl benzene  M-dimethyl benzene

1,4-dimethyl benzene  Para-dimethyl benzene  P-dimethyl benzene

Reactions

1) Substitution

 Saturated hydrocarbons ONLY go through substitution (other things can as well but most likely
won’t)

 “Rip off” a hydrogen and put in another atom

C2H6 + F2  C2H5F + HF

+  +
2) Addition

 Unsaturated hydrocarbons (not alkanes)

 A double or triple bond is broken so another functional group can be added

C2H4 + F2  C2H4F2

+ 

3) Halogenation

 Substitution or addition of a halogen for a hydrogen in a hydrocarbon

C2H6 + F2  C2H5F + HF (see above)

4) Hydrogenation

 Addition reaction that involves adding a hydrogen when a double or triple bond is broken

5) Hydration

 Hydration is the addition of water and will make a hydrogen and a hydroxide group

+ 
Functional Groups:

1) Alcohol (hydroxyl group): R-OH

 Non-electrolytes

 High boiling points due to H-bonding

 Primary alcohol has an OH (hydroxyl) at the end of a chain


 Secondary alcohol has an OH somewhere in the middle of a chain

 A tertiary or ternary alcohol has an OH in a separate branch

- You must write where the OH compound is on the hydrocarbon

 If there are 2 OH’s (dihydroxy) then add diol at the end of the word (1,2-Ethanediol is also called
ethylene glycol)

 If there are 3 OH’s (trihydroxy) then add triol at the end of the word (1,2,3-Propanetriol is also
called glycerol)
2) Aldehyde: RCHO

 Mild oxidation of a primary alcohol

 Simplest is methanal (AKA formaldehyde - preserving animals YUM)

3) Carboxylic Acid (Organic Acid) (“oic acid”): RCOOH

 Further oxidation of an aldehyde

Ethanoic Acid (AKA Acetic acid AKA Vinegar)

4) Ketones: (RCOR)

 Oxidation of a secondary alcohol

 Must write where the oxygen atom is

 Has a minimum of three carbons

 Carbon with a double bond oxygen is the carbonyl group

2-Propanone (don’t really need the 2 in this case but just to show how to name it)
5) Ether (…”oxy”…): (ROR’)

 Dehydration of 2 primary alcohols

6) Ester: (RCOOR’)

 Alcohol + Organic acid Ester + H2O

 Name alcohol derivative and change acid to oate

Methyl Ethanoate

+  +

Nitrogen Groups:

1) Amine

 NH2 off hydrocarbon

 Organic base

 Must write where the NH2 (NH? NH2 could only be on the end so it doesn’t matter unless you
have other things in there) is
2) Amide

 CO and NH2

3) Nitrile

 CN

4) Nitro
 NO2

 Amino acids are amphoteric (What does this have to do with nitro groups? But amino acids have

a carboxyl group AND amine group which makes them amphoteric NEAT!)

Glycine – an amino acid

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