Chapter 5 Stereochemistry
o For a carbon to be chiral, it must have four different groups bonded to it
Must be tetrahedral, but thats necessary for the above to be true
Thus, CH3 or CH2 will neve
Makes up less than 1% of the Earths crust
Si, Al, O2 are most prevalent
Not all carbon-containing material is considered organic
o Some inorganic carbon-containing materials are pure carbon (graphite,
diamond, Bucky Balls, nanotubes), c
Types of bonds
Sigma the overlap is directly between the two nuclei
o Every bond contains one (and only one) sigma bond
Pi the overlap is above and below the sigma bond
o These are formed by the overlap of unhybridized p orbitals
o There is one
Nomenclature of alkanes
Know up to dodecane
# of C
# of C
Find the longest chain
The longest chain is 7 carbons l
Addition of halogen to an alkane
Only works on sp3-hybridized carbons
Works best with chlorine and bromine
o Iodine is too slow
o Fluorine blows up (too fast)
Goes through radical intermediate, so putting halogen on more substitut
Chapter 6 Reactions of Alkyl Halides
Nucleophiles are Lewis Bases, so they must have a lone pair.
Negatively charged nucleophiles are stronger than their neutral
Nucleophile strength decreases from left to right on periodi
Chapter 7 Intro to Alkenes
Sigma vs. pi bonds
o Sigma bonds are stronger than pi bonds
o But remember that a double bond is the sum of the two, so it is stronger
than a single bond
Elements of unsaturation
o For every pi bond or ring you lose two hydrogen
Chapter 8 Reactions of Alkenes
o Regio vs stereoselectivity
Regio where do the pieces add?
Some reactions give anti-Markovnikov products
Markovnikovs rule hydrogen will go to the side of the
double bond with most hydrogens.
Chapter 9 Alkynes
o You name these just like you did alkenes
o When you have a molecule with double bonds and triple bonds, you name
it as an enyne
o Alkynes beat halogens and alkyl groups, but not alkenes
Oxidation in Organic terms
Addition of O, X2; loss of H2
Addition of H2; loss of O or X2
Anytime you oxidize one carbon but
reduce another (ex. Adding H and OH
to adjacent carbons)
Oxidation of alcohols
o Alcohols are classified much like alkyl halides - 1, 2, and 3
o Alcohols have precedence over alkenes and alkynes
Get to the hydroxyl first!
You do have to say 1 with straight-chain alcohols
Physical Properties of Ethers
Fairly low boiling point because there is no hydrogen-bonding in pure
Ethers can accept hydrogen bonds when in solution with hydrogenbonding compounds.
o Why ethers make good solvents
Dissolve a wide rang
Chapter 15 Conjugated Systems
What makes a conjugated system?
o When you have alternating double bonds, the electrons of the pi system
can flow over a longer length.
o This is conjugation.
Stabilities of Dienes
o Conjugated alternating double bonds
Chapter 16 Aromaticity
Structure and properties of benzene
Learn to recognize that C6H5 is a phenyl ring
Very common to see it this way on the ACS
o Empirical formula CH
o Very, very stable
The reactions of alkenes will not react with benze
Chapter 17 Reactions of Aromatic Compounds
Electrophilic Aromatic Substitution
General reaction - an electrophile replaces a hydrogen
Electrons of pi system attack strong electrophile, generating
resonance-stabilized carbocation intermediate (sigma
Chapter 18 Ketones and Aldehydes
Ketones have priority over alcohols
Find the longest chain with the carbonyl in it.
Name the parent and replace the e with one
Say where the carbonyl is.
When the ketone is not the high-priorit
Chapter 19 Amines
o Classification of amines
Amines are classified as 1, 2, or 3 based on how many R groups
are attached to the nitrogen
o Common names
Say the alkyl groups attached and then
Chapter 20 Carboxylic Acids
This is our highest priority group
Find the longest chain, drop the e and add oic acid
Decane decanoic acid
Structure and physical properties
Extended hydrogen bonding leads to high boiling points.
Chapter 21 Acid Derivatives
These notes will feel incomplete because I am only including the depth which Mr. Baker
requires for this material.
Acid derivatives in order of decreasing reactivity
Chapter 22 Enols and Enolates
Acidity of the hydrogen
o The position next door to a carbonyl is called the position
o When an proton is abstracted, the resulting carbanion is resonancestabilized.
This is called an enolate ion.
The pKa of mos