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Chapter 11. Saturated Hydrocarbons. Organic Chemistry. Study of Carbon compounds there are around 10 million, Called “Organic” because of the idea that these compounds were produced by the vital force Sugar, oil, fat, starch, protein. Importance. Bodies: Energy: Medicines:

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chapter 11

Chapter 11

Saturated Hydrocarbons

organic chemistry
Organic Chemistry
  • Study of Carbon compounds
    • there are around 10 million,
  • Called “Organic” because of the idea that these compounds were produced by the vital force
    • Sugar, oil, fat, starch, protein
importance
Importance
  • Bodies:
  • Energy:
  • Medicines:
  • Synthetics:
  • Soaps, detergents, cosmetics
  • Artificial body parts:
valence
Valence
  • Carbon – tetravalent
  • Nitrogen – trivalent
  • Oxygen - divalent
valence 2
Valence 2
  • Hydrogen/halogens – monovalent
  • Sulfur –
  • Phosphorous -
molecular formulas
Molecular Formulas
  • Shows number of atoms present
    • C6H12O6 C2H4O2
structural
Structural
  • Shows how atoms are arranged in the molecule
    • also known as a
    • must show
bonding in alkanes
Bonding in Alkanes
  • Each C forms
  • Tetrahedral geometry
  • All four bonds are equivalent
  • sp3 hybridization
  • VSEPR predicts 109.5o bond angle
practice
Practice
  • Draw: CH2F2, CH4, C2H6, C2H4, C2H2
  • Which is correct?
structural formulas
Structural Formulas
  • Condensed
  • Expanded
  • Skeleton
  • Line
families and functional groups
Families and Functional Groups
  • Functional Group - Specific atom or group of atoms or bonding arrangement
  • Alkanes
  • Alkenes
  • Alkynes
  • Aromatics
  • Alcohols
  • Ethers
families and functional groups1
Families and Functional Groups
  • Aldehydes
  • Ketones
  • Carboxylic acids
  • Esters
  • Amines
  • Amides
what family
What family?
  • To what family do each of the following belong?
alkanes
Alkanes
  • Obtained from oil and natural gas
  • Used for
  • Converted to
  • Contain only C-C and C-H
  • General formula:
  • http://www.lloydminsterheavyoil.com/unsaturated.htm
suffixes
Suffixes
  • -ane refers to
  • -ene refers to
  • -yne refers to
  • -anol refers to
  • -anal refers to
  • -anoic acid refers to
  • -anone refers to
iupac rules for naming
IUPAC Rules for Naming
  • ID and name the longest chain
  • Base name accounts for only C in longest chain. Attached Carbons are called
    • Name(s) of alkyl groups in front of base
    • Use prefixes
    • Alphabetize
naming
Naming
  • Number the carbons in

Number from the end

  • In front of the alkyl name,
  • Use hyphens to separate numbers from words, commas to separate numbers
naming alkanes
Naming Alkanes
  • Designation of Carbons as
  • Determined by the number of bonded Carbons,
  • Functional groups
  • Alkyl Groups
constitutional isomers
Butane

mp -138oC

bp - 1oC

Isobutane

mp -159oC

bp - 12oC

Constitutional Isomers

Same Formula: Butane and isobutane (2-methyl propane) C4H10

Differ in connectivity and properties

constitutional isomers1
Constitutional Isomers
  • Basic difference is
  • Also called
  • Butane is
  • Isobutane is
  • More total C = more isomers
  • Draw isomers for C5H12 (there are 3)
cycloalkanes
Cycloalkanes
  • Rings
  • Glucose, starch, cholesterol, hormones
  • Often represented by
  • Rules for naming
    • base name is
    • names of substituents placed before base name. Numbers indicate placement and correct name has lowest numbers.
constitutional isomers2
Constitutional Isomers
  • Cycloalkanes have the general formula
  • How many isomers can you draw for C6H12
cis trans stereoisomerism
Cis-Trans Stereoisomerism
  • C-C bond in cycloalkanes have
  • Certain cycloalkanes posses
  • C5H10 - there are 6 cycloalkanes
  • Two of interest
cis trans
Cis-Trans
  • Stereoisomerism results
  • In this case -
  • Also called diastereomers
  • Properties of 1,2-dimethylcyclopropane
    • cis- bp = 37oC
    • trans- bp = 29oC
  • Stereocenter
cis trans isomers
Cis-trans isomers
  • Which of the following exist as cis and trans isomers?
physical properties of alkanes
Intermolecular forces

play major role in properties

Cyclo and Alkanes

Molecular mass

“Squashiness”

Tables 11.3, 11.5, pp 293, 208

Physical properties of alkanes
physical properties
Physical Properties
  • Shape
    • Cycloalkane>straight-chain>branched
    • Donut>Sphere>Linked sausages
  • Solubility
    • Like dissolves like
predict boiling point
Predict Boiling point
  • Which has higher b.p?
    • heptane or hexane
    • cyclobutane or cycloheptane
    • nonane or 3-methylnonane
chemical properties
Chemical Properties
  • C-C and C-H bonds are stable.
  • Combustion
    • Burning in
    • Produces about 15,000 kJ/lb of fuel
    • Complete and incomplete
halogenation
Halogenation
  • Addition of a halogen to an alkane
  • Halothane CF3CHBrCl is an anesthetic
  • 1,2,3,4,5,6-hexacholorcyclohexane is an insecticide
  • Freon - dichlorodifluoromethane
halogenation1
Halogenation
  • Write the reaction for the monochlorination of
  • Naming of alkyl halides
    • IUPAC rules apply
  • Name CH3CH2CHClCH2CH3
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