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Chapter 11

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

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  1. Chapter 11 Saturated Hydrocarbons

  2. 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

  3. Importance • Bodies: • Energy: • Medicines: • Synthetics: • Soaps, detergents, cosmetics • Artificial body parts:

  4. Valence • Carbon – tetravalent • Nitrogen – trivalent • Oxygen - divalent

  5. Valence 2 • Hydrogen/halogens – monovalent • Sulfur – • Phosphorous -

  6. Molecular Formulas • Shows number of atoms present • C6H12O6 C2H4O2

  7. Structural • Shows how atoms are arranged in the molecule • also known as a • must show

  8. Bonding in Alkanes • Each C forms • Tetrahedral geometry • All four bonds are equivalent • sp3 hybridization • VSEPR predicts 109.5o bond angle

  9. Practice • Draw: CH2F2, CH4, C2H6, C2H4, C2H2 • Which is correct?

  10. Structural Formulas • Condensed • Expanded • Skeleton • Line

  11. Families and Functional Groups • Functional Group - Specific atom or group of atoms or bonding arrangement • Alkanes • Alkenes • Alkynes • Aromatics • Alcohols • Ethers

  12. Families and Functional Groups • Aldehydes • Ketones • Carboxylic acids • Esters • Amines • Amides

  13. What family? • To what family do each of the following belong?

  14. 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

  15. Base Names

  16. Suffixes • -ane refers to • -ene refers to • -yne refers to • -anol refers to • -anal refers to • -anoic acid refers to • -anone refers to

  17. Putting it together!

  18. 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

  19. Substituent names

  20. 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

  21. Naming Alkanes • Designation of Carbons as • Determined by the number of bonded Carbons, • Functional groups • Alkyl Groups

  22. 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

  23. Constitutional Isomers • Basic difference is • Also called • Butane is • Isobutane is • More total C = more isomers • Draw isomers for C5H12 (there are 3)

  24. 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.

  25. Constitutional Isomers • Cycloalkanes have the general formula • How many isomers can you draw for C6H12

  26. Cis-Trans Stereoisomerism • C-C bond in cycloalkanes have • Certain cycloalkanes posses • C5H10 - there are 6 cycloalkanes • Two of interest

  27. Cis-Trans • Stereoisomerism results • In this case - • Also called diastereomers • Properties of 1,2-dimethylcyclopropane • cis- bp = 37oC • trans- bp = 29oC • Stereocenter

  28. Cis-trans isomers • Which of the following exist as cis and trans isomers?

  29. 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

  30. Physical Properties • Shape • Cycloalkane>straight-chain>branched • Donut>Sphere>Linked sausages • Solubility • Like dissolves like

  31. Predict Boiling point • Which has higher b.p? • heptane or hexane • cyclobutane or cycloheptane • nonane or 3-methylnonane

  32. Chemical Properties • C-C and C-H bonds are stable. • Combustion • Burning in • Produces about 15,000 kJ/lb of fuel • Complete and incomplete

  33. 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

  34. Halogenation • Write the reaction for the monochlorination of • Naming of alkyl halides • IUPAC rules apply • Name CH3CH2CHClCH2CH3

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