Chapter 12 Organic Chemistry: The Infinite Variety of Carbon Compounds

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Chapter 12 Organic Chemistry The Infinite
Variety of Carbon Compounds
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Organic Chemistry

• Chemistry of carbon-containing compounds
• Most of these come from living things
• Not necessarily the case
• 30 million chemical compounds known
• 95 are compounds made of carbon

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Carbon

• Able to bond strongly to other carbon atoms
• Forms long chains
• Very few other atoms can form short chains, let
  alone long chains
• Capable of forming ring structures
• Bonds strongly to other elements
• In particular, H, O, and N

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Hydrocarbons

• Made of carbon and hydrogen
• Several classes
• Alkanes
• Contain only single bonds
• Saturated hydrocarbons
• Each C atom bonded to maximum number of H atoms

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Alkanes

• Chemical formula CnH2n2 n 1, 2, 3,
• CH4, methane, simplest one
• C2H6, ethane
• All have ane ending
• Follow a pattern

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• Condensed structural formulas
• Show how many hydrogens are attached to each
  carbon
• CH3-CH3 for ethane
• Structural formulas show how atoms are bonded
  together

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Isomerism

• Isomers compounds with same molecular formula
  but different structural formulas
• Differences in structure may give rise to
  differences in chemical and physical properties

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• Number of possible isomers increases rapidly with
  the number of carbons
• C30H62 gt4 billion possible isomers

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Properties of Alkanes

• Main property will burn

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Cyclic Hydrocarbons

• Carbon atom chains in form of rings
• Can be represented by structural formulas or
  symbolic representations

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Unsaturated Hydrocarbons

• Can have more hydrogen atoms added
• Very important in biological systems
• Alkene hydrocarbon that contains one or more
  carbon-to-carbon double bonds
• General formula of CnHn
• Simplest ethylene, C2H4

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• Alkyne hydrocarbon that contains one or more
  carbon-to-carbon triple bonds
• General formula of CnH2n2
• Simplest acetylene, C2H2

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Properties of Alkenes and Alkynes

• Similar physical properties to alkanes
• Undergo more reactions than alkanes
• Addition reaction add compounds across double
  bond
• Importantly, they can form polymers

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Aromatic Hydrocarbons

• Contain double or triple bonds, but do not show
  the same reactivity as other unsaturated
  hydrocarbons
• Benzene C6H6
• Used mainly as solvents

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Chlorinated Hydrocarbons

• Add Cl to hydrocarbons
• Increase reactivity of alkanes
• Dissolve fats, oils, and greases
• Useful for dry cleaning
• Tend to accumulate in fatty tissues
• If toxic, this will be a problem

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Chlorofluorocarbons and Fluorocarbons

• Tend to be either liquids or gases
• Completely inert
• Except in upper atmosphere
• O2 soluble in fluorinated compounds
• Temporary substitute for hemoglobin

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Functional Groups

• Group of atoms that gives a family of organic
  compounds its characteristic chemical and
  physical properties
• Alkyl group derived from alkane by removing a H
• R stands for alkyl group in general

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Alcohol Family

• OH group
• Replace -e with -ol
• CH3OH, methanol, simplest
• Produced industrially
• Mainly a chemical intermediate

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• C2H5OH, ethanol
• Made industrially and by fermentation
• Industrially produced alcohol has noxious
  substances added
• Small, simple alcohols tend to be toxic

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Multifunctional Alcohols

• Several common alcohols have more than one OH
  group
• Ethylene glycol main ingredient in antifreeze
• Glycerol used in lotions
• Ingredent in some explosives

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Phenol

• OH group on benzene ring
• Different chemical properties than other alcohols
• Behaves more like an acid
• First antiseptic
• Also causes skin irritation

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Ethers

• Two alkyl groups attached to same O
• Example CH3CH2-O-CH2CH3
• Used mainly as solvent
• Little chemical reactivity
• Insoluble in water
• Highly flammable

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Aldehydes and Ketones

• Both contain carbonyl group (CO)
• Aldehyde R-CHO
• Ketone R-CO-R

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Common Aldehydes

• Change -e ending to -al
• Produced by oxidation of alcohols
• Formaldehyde used as a preservative
• Larger ones used as fragrances
• Benzaldehyde flavor in maraschino cherries

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Common Ketones

• Change -e ending to -one
• Acetone most common ketone
• Used primarily as a solvent
• Produced by oxidation of alcohols

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Carboxylic Acid

• Contains CO and OH group on same carbon
• Change -e to -oic acid
• Acetic acid acid in vinegar

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Esters

• Derived from carboxylic acids and alcohols
• Tend to be fragrant
• Methyl butyrate apple
• Ethyl butyrate pineapple
• Ethyl formate rum
• Methyl salicylate wintergreen

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Amines

• Contain N
• May have 1, 2, or 3 alkyl or aromatic groups
• Most biological amines are amino acids
• Building blocks of proteins

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Amides

• N bonded directly to carbonyl group
• Linkage that holds proteins together

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Heterocyclic Compounds

• Ring compounds that have something other than C
  in the ring
• Occur in plants
• Alkaloids basic in solution
• Examples caffeine, morphine, cocaine
• Form basic structure of DNA