Chapter 11
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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

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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:

  • Synthetics:

  • Soaps, detergents, cosmetics

  • Artificial body parts:


Valence

  • Carbon – tetravalent

  • Nitrogen – trivalent

  • Oxygen - divalent


Valence 2

  • Hydrogen/halogens – monovalent

  • Sulfur –

  • Phosphorous -


Molecular Formulas

  • Shows number of atoms present

    • C6H12O6C2H4O2


Structural

  • Shows how atoms are arranged in the molecule

    • also known as a

    • must show


Bonding in Alkanes

  • Each C forms

  • Tetrahedral geometry

  • All four bonds are equivalent

  • sp3 hybridization

  • VSEPR predicts 109.5o bond angle


Practice

  • Draw: CH2F2, CH4, C2H6, C2H4, C2H2

  • Which is correct?


Structural Formulas

  • Condensed

  • Expanded

  • Skeleton

  • Line


Families and Functional Groups

  • Functional Group - Specific atom or group of atoms or bonding arrangement

  • Alkanes

  • Alkenes

  • Alkynes

  • Aromatics

  • Alcohols

  • Ethers


Families and Functional Groups

  • Aldehydes

  • Ketones

  • Carboxylic acids

  • Esters

  • Amines

  • Amides


What family?

  • To what family do each of the following belong?


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


Base Names


Suffixes

  • -ane refers to

  • -ene refers to

  • -yne refers to

  • -anol refers to

  • -anal refers to

  • -anoic acid refers to

  • -anone refers to


Putting it together!


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


Substituent names


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

  • Designation of Carbons as

  • Determined by the number of bonded Carbons,

  • Functional groups

  • Alkyl Groups


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 Isomers

  • Basic difference is

  • Also called

  • Butane is

  • Isobutane is

  • More total C = more isomers

  • Draw isomers for C5H12 (there are 3)


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 Isomers

  • Cycloalkanes have the general formula

  • How many isomers can you draw for C6H12


Cis-Trans Stereoisomerism

  • C-C bond in cycloalkanes have

  • Certain cycloalkanes posses

  • C5H10 - there are 6 cycloalkanes

  • Two of interest


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

  • Which of the following exist as cis and trans isomers?


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

  • Shape

    • Cycloalkane>straight-chain>branched

    • Donut>Sphere>Linked sausages

  • Solubility

    • Like dissolves like


Predict Boiling point

  • Which has higher b.p?

    • heptane or hexane

    • cyclobutane or cycloheptane

    • nonane or 3-methylnonane


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

  • Addition of a halogen to an alkane

  • Halothane CF3CHBrCl is an anesthetic

  • 1,2,3,4,5,6-hexacholorcyclohexane is an insecticide

  • Freon - dichlorodifluoromethane


Halogenation

  • Write the reaction for the monochlorination of

  • Naming of alkyl halides

    • IUPAC rules apply

  • Name CH3CH2CHClCH2CH3


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