Organic Chemistry

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organic chemistry

studies millions of compounds which are always made up of carbon and hydrogen and sometimes include oxygen, nitrogen and sulfur

characteristics of organic compounds

1. covalent bonds 2. nonpolar 3. insoluble in water 4 low melting point, low boiling point, low density 5. some have isomers

isomer

compound with the same molecular formula but different structural formula

how many bonds does carbon have

always has 4 bonds

how many bonds does hydrogen have

always has 1 bond

how many bonds does oxygen have

always has 2 bonds

how many bonds does nitrogen have

always has 3 bonds

how many bonds does sulfur have

always has 2 bonds

types of hydrocarbons (C & H)

alkane, alkene, alkyne, aromatic

compounds with C, H and O

ketones, carboxylic acid, esters, alcohols, aldehydes, ether

compounds with C, H, N, maybe O

amines, nitriles, amides

hydrocarbons prefixes

C1 - meth; C2 - eth; C3 - prop; C4 - but; C5 - pent; C6 - hex; C7 - hept; C8 - oct; C9 - non; C10 - deca; Cn - alk

hydrocarbon suffixes

CnH2n+2 = alkANE; CnH2n = alkENE; CnH2n-2 = alkYNE; CnH2n-6 = aromatic

alkanes also known as?

parafines or saturated hydrocarbons

alkane characteristics (5)

1. saturated (have ONLY single bonds- no double or triple) and do not add anything to their formula; 2. good fuels; 3. nonpolar 4. insoluble in water; 5. exhibit only LDF

gaseous alkenes

C1-C4; have no color no smell

liquid alkenes

C5-C14 (gasoline, diesel, jet fuel, kerosene...)

solid alkenes

C15-... (vaseline, tar, asphalt)

alkyl (R-) group of alkanes

those compounds of the alkane group with one H removed from the end or middle (CnH2n+2-1)

alkane formulas and names

C1H4 - methane; C2H6 - ethane; C3H8 - propane; C4H10 - butane; C5H12 - pentane; C6H14 - hexane; C7H16 - heptane; C8H18 - octane; C9H20 - nonane; C10H22 - decane

alkene formulas and names

C1H2 (DOES NOT EXIST - C must have 4 bonds); C2H4 - ethene; C3H6 - propene; C4H8 - butene; C5H10 - pentene; C6H12 - hexene; C7H14 - heptene; C8H16- octene; C9H18 - nonene; C10H20 - decene

alkyne formulas and names

C1H0 doe not exist; C2H2 - ethyne; C3H4 - propyne; C4H6 - butyne; C5H8 - pentyne; C6H10 - hexyne; C7H12 - heptyne; C8H14 - octyne; C9H16 - nonyne; C10H18 - decyne

alkyl names and formulas

CH3 - methyl; C2H5 - ethyl; C3H7 - propyl; C4H9 - butyl; C5H11 - pentyl; C6H13 - hexyl; C7H15 - heptyl; C8H17 - octyl; C9H19 - nonyl; C10H21 - decyl

alkanes that do not have isomers

CH4, C2H6, C3H8

alkene characteristics

1. are unsaturated (have at least 1 double bond), and can have addition reactions, polymerization reactions and oxidation reactions; 2. can have constitutional and geometric isomers

geometric isomers of alkenes

cis (boat shape), trans (chair shape)

addition reactions of alkenes

pi bond is broken and two atoms can be added to the molecule

types of additional reactions of alkenes

1. addition of H2 (hydrogenation); 2. addition of a halogen (halogenation); 3. addition of HCl, HBr or HI; 4. addition of H20 (hydration)

Markovnikov's Rule

in addition of HX to pi bond of alkene, H goes to C with more H and X goes to C with less H

alkyne characteristics

unsaturated and can undergo addition reactions

types of alkyne addition reactions

1. H2 (hydrogenation); 2. halogen (halogenation); 3. HX; 4. water (hydration)

hydration reaction in alkyne forms?

ketone or aldehyde

what must aromatic compounds contain?

a benzene ring

benzene characteristics

1. liquid with a nice odor; 2. good solvent; 3. is a carcinogen and can cause cancer

important aromatic hydrocarbons

1. toluene (methylbenzene); 2. xylene (Orthoxylene, Metaxylene, Paraxylene); 3. nepthalene; 4. phenol; 5. aniline; 6. benzaldehyde; 7. benzoic acid

toluene (methylbenzene) formula

C7H8

orthoxylene formula

C8H10; X on 1, 2

metaxylene formula

C8H10; X on 1, 3

paraxylene formula

C8H10; X on 1, 4

nepthalene formula

C10H8 (two benzenes connected and sharing one side)

phenol formula

C6H5OH

aniline formula

C6H5NH2

benzaldehyde formula

C6H5CHO

benzoic acid formula

C6H5COOH

primary carbon

linked to carbon on only 1 side

secondary carbon

linked to carbon on 2 sides

tertiary carbon

linked to carbon on 3 sides

quarternary carbon

linked to carbon on 4 sides

hydrocarbon characteristics (3)

nonpolar, insoluble in H2O, exhibit LDF

alcohol characteristics (3)

highly polar, highly soluble in water up to C4, h-bond

carboxylic acid characteristics (3)

highly polar, highly soluble in water up to C4, h-bond

primary and secondary amine characteristics (3)

highly polar, highly soluble in water up to C4, h-bond

ether characteristics (3)

polar, more or less soluble up to C4, exhibits DDF

aldehyde characteristics (3)

polar, more or less soluble up to C4, exhibits DDF

ketone characteristics (3)

polar, more or less soluble up to C4, exhibits DDF

carboxylic acid characteristics (3)

polar, more or less soluble up to C4, exhibits DDF

tertiary amine characteristics (3)

polar, more or less soluble up to C4, exhibits DDF

oxidation

removing a hydrogen or adding an oxygen to a compound

reduction

adding a hydrogen or removing an oxygen to a compound

hydrating an alkene

adding H2O to a pi bond; creates alcohol

polymerization

joining MANY molecules of a small alkene (C2H4 or C3H6)and forming a very large molecule called a polymer; requires a double bond (alkene)

estrification

acid + alcohol = water + ester

boiling point, melting point, solubility

acid > alcohol > amine > aldehyde, ketone, amide > hydrocarbons

chirol carbon

carbon which is linked to 4 DIFFERENT atoms or groups of atoms

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