Updated April 2007Created by C. Ippolito April 2007 Organic Chemistry Objectives 1.State general...

Updated April 2007 Created by C. IppolitoApril 2007

Organic ChemistryOrganic Chemistry

Objectives1. State general properties and reactions

of organic compounds2. Compare general formulas and name

hydrocarbons3. Compare saturated and unsaturated

compounds4. State names, formulas, and uses for

hydrocarbon derivatives

Objectives1. State general properties and reactions

of organic compounds2. Compare general formulas and name

hydrocarbons3. Compare saturated and unsaturated

compounds4. State names, formulas, and uses for

hydrocarbon derivatives


Hydrocarbons

• simplest compounds– only carbon and hydrogen

• aliphatic hydrocarbons– open chains of carbon and hydrogen

• cyclic hydrocarbons– closed “ring” chains of carbon and hydrogen


Saturated Hydrocarbons

• contain only carbon to carbon single bonds

• contain “maximum” hydrogen


Unsaturated Hydrocarbons

• contain at least one carbon to carbon double or triple bonds

• contain less than “maximum” hydrogen


Hydrocarbon Series

• Alkanes– only single bonds, saturated, CnH2n+2

• Alkenes– double bond, unsaturated, CnH2n

• Alkynes– triple bond, unsaturated CnH2n-2

• Alkadienes– two separate double bonded carbons


Homologous Series

• constant increment of change in molecular structure

• 1 = meth-• 3 = prop-• 5 = pent-• 7 = hept-• 9 = non-

• 2 = eth-• 4 = but-• 6 = hex- • 8 = oct-• 10 = dec-


Formulas

• Molecular Formula – C4H10

• Structural Formula – • Condensed Structural Formulas

CH3-CH2-CH2-CH3

CH3CH2CH2CH3

CH3(CH2)2CH3

• Carbon Skeleton – C-C-C-C• Line Angle Formula -


Branched Chains• Parent ChainParent Chain

– longest continuous carbon chain• SubstituentsSubstituents

– atoms or atom groups replacing a hydrogen atom• alkyl groups

– hydrocarbon substituents» CH3― methyl group» CH3CH2― ethyl group» CH3CH2CH2― propyl group


IUPAC Naming Rules1. Find longest chain (parent)2. Number carbons3. Add numbers to substituent

groups4. Use prefixes for multiple

appearances of same group5. List substituents in alpha order6. Use punctuation but no spaces


IUPAC Naming


Properties of Alkanes• 1-4 C – gas• 5-16 C - liquid• >16 C – solid• nonpolar molecules

Created By C. IppolitoDec 2006


Structural Isomers• compounds with the same molecular

formula but different structures– different physical and chemical

properties


Stereoisomers• atoms joined in same order but

positions in space are different– Geometric IsomersGeometric Isomers

• orientation around rigid double bond– cis configuration

» groups on same side of double bond– trans configuration

» groups on different sides of double bond

– Optical IsomersOptical Isomers• four different groups attached to an

asymmetric carbon


Geometric Isomers


Optical Isomers


Cyclic Hydrocarbons

• hydrocarbon chain forms a ring– cyclopropane– cyclobutane– cyclopentane– cyclohexane


Aromatic Hydrocarbons

• contains a benzene ring– electrons shared evenly– “resonance”

• phenyl group– benzene sub


Substituted Benzene

• dimethyl benzene – 3 isomers– ortho-

• 1,2 dimethyl benzene– o-xylene

– meta-• 1,3 dimethyl benzene

– m-xylene

– para-• 1,4 dimethyl benzene

– p-xylene


Hydrocarbons in Crust• Natural Gas

– low molar mass• 80% methane, 10%

ethane, 4% propane, 2% butane

• Petroleum– fractional distillation

• separation by boiling points

– cracking• heat to form smaller

chains from larger ones


Functional Groups

• specific atomic arrangements that give specific physical and chemical propertieshydroxylcarbonylcarboxylaminoamido

alcoholaldehyde ketoneorganic acidamineamide


Alcohols• < 4 water soluble – polar• Primary – 1C on C-OH• Secondary – 2C on C-OH• Tertiary – 3C on C-OH• Dihydroxy & Trihydroxy (glycerol)


Common Alcohols and Uses

• methanol [1C]• ethanol [2C]• isopropanol [3C]• 1,2 ethandiol• glycerol

• solvent• antiseptic• antiseptic• antifreeze• fat

component


Carboxylic Acids

• Carboxyl group – carbonyl and hydroxyl group on same carbon– Latin & Greek names for sources

• methanoic acid [1C] (formic) – ant• ethanoic [2C] (acetic) – vinegar• propanoic [3C] – • butanoic [4C] –

– rest are not miscible in water “fatty acids” used to form “fats” with glycerol


Esters

• derivative of carboxylic acid and alcoholR1-COO-R2

– pleasant fruity odors

– used in fragrances


Ethers

• Compound in which oxygen is bonded to two carbon groupsGeneral Formula: R-O-R– ethylmethyl ether

• CH3CH2-O-CH3

– diethyl ether• CH3CH2-O-CH2CH3


Aldehyde / Ketone

• -C=O– aldehyde – has at least 1 H on –C=O

• methanal (formaldehyde) – preservative• ethanal (acetaldehyde) – “hangover”• benzaldehyde – almond odor

– ketone – all C on –C=O• propanone (acetone) – nail polish

remover


Organic Reactions• Substitution

– atom/group replaced with another• usually H replaced by halogens

CH4 + Cl2 HCl + CH3Cl (chloromethane)

• Addition– atoms added across double/triple

bond• hydrogenation – used to solidify

liquid vegetable oils• hydration – add water across double

bond forming an alcohol


Organic Reactions (con’t)

• Esterification– dehydration or condensation reaction

between an acid and alcohol


Organic Reactions (con’t)

• Saponification– hydrolysis of a fat with base (NaOH)

to form glycerol and soap (salt of fat)


Polymerization

• Polymer– large molecule made of repeating units

(monomers)• Natural Polymers

– proteins (amino acids)– polysaccharides (glucose)– nucleic acids (nucleotides)

• Synthetic Polymers– plastics (polystyrene, polyvinyl chloride – PVC)– nylons– polyester– teflon (polytetrafluoroethene – PTFE)

Updated April 2007Created by C. Ippolito April 2007 Organic Chemistry Objectives 1.State general...

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