Brief! Organic Chemistry for AP

Alkanes Hydrocarbon chains where all the bonds between carbons are SINGLE bondsHydrocarbon chains where all the bonds between carbons are SINGLE bonds Name uses the ending –aneName uses the ending –ane Examples: Methane, Propane, Butane, Octane, 2-methylpentaneExamples: Methane, Propane, Butane, Octane, 2-methylpentane

Prefixes for # of Carbons 1Meth6Hex 2Eth7Hept 3Prop8Oct 4But9Non 5Pent10Dec

Endings Alkanes (all C-C single bonded parent chain) end in –aneAlkanes (all C-C single bonded parent chain) end in –ane –Methane CH 4 –Ethane C 2 H 6 –Propane C 3 H 8 Attached carbon groups (substituents) end in –ylAttached carbon groups (substituents) end in –yl –Methyl CH 3 - –Ethyl CH 3 CH 2 - –Propyl CH 3 CH 2 CH 2 – –Propyl CH 3 CH 2 CH 2 – 3-ethylpentane

Names of attached groups Carbon (alkyl) groupsCarbon (alkyl) groups –Methyl CH 3 - –Ethyl CH 3 CH 2 - –Propyl CH 3 CH 2 CH 2 – HalogensHalogens –Fluoro (F-) –Chloro (Cl-) –Bromo (Br-) –Iodo (I-)

Designate the Location Designate the location (number of the carbon on the parent chain) for each attached group methyl

Some Simple Alkanes 2-methylpentane2-methylpentane 3-ethylhexane3-ethylhexane 2,2-dimethylbutane2,2-dimethylbutane 2,3-dimethylbutane2,3-dimethylbutane

Structural Formulas “Lazy” way to write the Hydrogens Instead of drawing the bonds, just state how many hydrogens are attached NOTE: The bonds are between CARBONS in a parent chain, and not hydrogens! Structural Formula Lewis Structure

Drawing and Naming Cycloalkanes Cycloalkanes are represented by polygons. A triangle represents cyclopropane, a square represents cyclobutane, a pentagon represents cyclopentane, and so on.

Isomers Straight chain alkanes: An alkane that has all its carbons connected in a row. Straight chain alkanes: An alkane that has all its carbons connected in a row. Branched chain alkanes: An alkane that has a branching connection of carbons. Branched chain alkanes: An alkane that has a branching connection of carbons. Isomers: Compounds with same molecular formula but different structures. Isomers: Compounds with same molecular formula but different structures.

However, carbons in butane (C 4 H 10 ) can be arranged in two ways; four carbons in a row (linear alkane) or a branching (branched alkane). These two structures are two isomers for butane.

Different isomers are completely different compounds. They have different structures, different physical properties such as melting point and boiling point, and may have different physiological properties.Different isomers are completely different compounds. They have different structures, different physical properties such as melting point and boiling point, and may have different physiological properties.

Learning Check Draw all possible structural isomers of C 5 H 12

Alkenes and Alkynes Unsaturated –contain carbon-carbon double and triple bond to which more hydrogen atoms can be added. Alkenes: carbon-carbon double bonds Alkynes: carbon-carbon triple bonds.

Naming Alkenes and Alkynes When the carbon chain has 4 or more C atoms, number the chain to give the lowest number to the double or triple bond CH 2 =CHCH 2 CH 3 1-butene CH 3 CH=CHCH 3 2-butene CH 3 C  CCH 3 2-butyne

Aromatic Compounds and Benzene Aromatic compounds contain benzene. Benzene, C 6 H 6, is represented as a six carbon ring with 3 double bonds. Two possible resonance structures can be drawn to show benzene in this form.

Functional Groups

The Common Functional Groups ClassGeneral Formula HalohydrocarbonsR  X AlcoholsR  OH EthersR  O  R Aldehydes

The Common Functional Groups ClassGeneral Formula Ketones Carboxylic Acids Esters AminesR  NH 2

Polymers...are large, usually chainlike molecules that are built from small molecules called monomers. MonomerPolymer EthylenePolyethylene Vinyl chloridePolyvinyl chloride TetrafluoroethyleneTeflon

Types of Polymerization Addition Polymerization: monomers “add together” to form the polymer, with no other products. (Teflon) Condensation Polymerization: A small molecule, such as water, is formed for each extension of the polymer chain. (Nylon)

Alkanes from Carbon and Hydrogen Alkanes are carbon compounds that contain only single bonds. The simplest alkanes are hydrocarbons – compounds that contain only carbon and hydrogen. Hydrocarbons are used mainly as fuels, solvents and lubricants:

Hydrocarbons

IUPAC System of Naming Organic Compounds

Structural Isomers How many structural isomers – compounds with the same chemical formula but different connectivity – are there with the formula C 7 H 16 ?

Cycloalkanes

Naming Cycloalkanes The above compounds are not structural isomers. Their connectivity is identical. They are stereoisomers – compounds that differ in how substituents are arranged in space Unlike "floppy" chains, rings have an additional consideration for multiple substitutions:

Naming Cycloalkanes

2 Carbon molecules AlcoholsEthers EstersAcids ethanol dimethyl ether ethanoic acidmethyl methanoate Aldehydes ethanal No ketones are possible (3 C minimum) Ketones AminesAmides dimethylamine ethylamine ethanamide

3 Carbon molecules Aldehydes Amines Ketones propanal2-propanone propylamine ethylmethylamine trimethylamine Amides propanamide CHCH 3 NH 2 CH 3 isopropylamine

3 Carbon molecules 1-propanol 2-propanol Alcohols Ethers Ethyl methyl ether Propanoic acid Esters Methyl ethanoateEthyl methanoate Acids

4C alcohols 1-butanol 2-butanol 1-isobutanol, 2-methyl-1-propanol 2-isobutanol, 2-methyl-2-propanol

4C ethers methyl propyl ether diethyl ether isopropyl methyl ether

4C carboxylic acids butanoic acid isobutanoic acid, 2-methylpropanoic acid

4C esters methyl propanoate ethyl ethanoate propyl methanoateisopropyl methanoate

4C aldehydes butanal isobutanal, 2-methylpropanal

4C ketones 2-butanone, (butanone)

4C amines diethylamine isopropylmethylamine isobutylamine butylamine methylpropylamine ethyldimethylamine

4C amides butanamide isobutanamide, 2-methyl-propanamide For more lessons, visit

Which of the following is an aldehyde?

Which of the following is an ester?

Which of the following is an amide?

An organic compound is water soluble only if it contains one polar functional group capable of hydrogen bonding with the solvent for every five C atoms it contains. For example, compare the solubility of butane and acetone in H 2 O and CCl 4.

Since butane and acetone are both organic compounds having a C—C and C—H backbone, they are soluble in the organic solvent CCl 4. Butane, which is nonpolar, is insoluble in H 2 O. Acetone is soluble in H 2 O because it contains only three C atoms and its O atom can hydrogen bond with an H atom of H 2 O.

The size of an organic molecule with a polar functional group determines its water solubility. A low molecular weight alcohol like ethanol is water soluble since it has a small carbon skeleton of  five C atoms, compared to the size of its polar OH group. Cholesterol has 27 carbon atoms and only one OH group. Its carbon skeleton is too large for the OH group to solubilize by hydrogen bonding, so cholesterol is insoluble in water.

The nonpolar part of a molecule that is not attracted to H 2 O is said to be hydrophobic. The polar part of a molecule that can hydrogen bond to H 2 O is said to be hydrophilic. In cholesterol, for example, the hydroxy group is hydrophilic, whereas the carbon skeleton is hydrophobic.