updated april 2007created by c. ippolito april 2007 organic chemistry objectives 1.state general...
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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
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Updated April 2007 Created by C. IppolitoApril 2007
Hydrocarbons
• simplest compounds– only carbon and hydrogen
• aliphatic hydrocarbons– open chains of carbon and hydrogen
• cyclic hydrocarbons– closed “ring” chains of carbon and hydrogen
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Saturated Hydrocarbons
• contain only carbon to carbon single bonds
• contain “maximum” hydrogen
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Unsaturated Hydrocarbons
• contain at least one carbon to carbon double or triple bonds
• contain less than “maximum” hydrogen
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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
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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-
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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 -
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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
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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
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IUPAC Naming
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Properties of Alkanes• 1-4 C – gas• 5-16 C - liquid• >16 C – solid• nonpolar molecules
Created By C. IppolitoDec 2006
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Structural Isomers• compounds with the same molecular
formula but different structures– different physical and chemical
properties
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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
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Geometric Isomers
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Optical Isomers
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Cyclic Hydrocarbons
• hydrocarbon chain forms a ring– cyclopropane– cyclobutane– cyclopentane– cyclohexane
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Aromatic Hydrocarbons
• contains a benzene ring– electrons shared evenly– “resonance”
• phenyl group– benzene sub
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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
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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
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Functional Groups
• specific atomic arrangements that give specific physical and chemical propertieshydroxylcarbonylcarboxylaminoamido
alcoholaldehyde ketoneorganic acidamineamide
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Alcohols• < 4 water soluble – polar• Primary – 1C on C-OH• Secondary – 2C on C-OH• Tertiary – 3C on C-OH• Dihydroxy & Trihydroxy (glycerol)
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Common Alcohols and Uses
• methanol [1C]• ethanol [2C]• isopropanol [3C]• 1,2 ethandiol• glycerol
• solvent• antiseptic• antiseptic• antifreeze• fat
component
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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
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Esters
• derivative of carboxylic acid and alcoholR1-COO-R2
– pleasant fruity odors
– used in fragrances
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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
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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
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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
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Organic Reactions (con’t)
• Esterification– dehydration or condensation reaction
between an acid and alcohol
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Organic Reactions (con’t)
• Saponification– hydrolysis of a fat with base (NaOH)
to form glycerol and soap (salt of fat)
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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)