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Chapter 19: Organic chemistry

Chapter 19: Organic chemistry. Chemistry 1020: Interpretive chemistry Andy Aspaas, Instructor. Organic compounds. Organic compounds: carbon containing compounds Specifically, with carbon-carbon covalent bonds Carbonates, CO 2 , CO are not organic VSEPR theory: carbon has 4 electron pairs

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Chapter 19: Organic chemistry

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  1. Chapter 19: Organic chemistry Chemistry 1020: Interpretive chemistry Andy Aspaas, Instructor

  2. Organic compounds • Organic compounds: carbon containing compounds • Specifically, with carbon-carbon covalent bonds • Carbonates, CO2, CO are not organic • VSEPR theory: carbon has 4 electron pairs • A tetrahedral electron pair arrangement • 4 covalent bonds, no lone pairs • Tetrahedral molecular shape as well

  3. Hydrocarbons and alkanes • Hydrocarbons contain only carbon and hydrogen • Alkanes are hydrocarbons with only single bonds (no double or triple bonds) • Saturated: only single bonds • Simplest alkane: methane, CH4 • Ethane, molecular formula C2H6 • Structural formula (indicates connectivity) is CH3CH3

  4. Straight-chain alkanes (1 C through 4 C) • Straight-chain (or “normal”) alkanes have carbons all attached in a row • n- at beginning indicates straight-chain (normal)

  5. Straight-chain alkanes (5 C through 10 C) • For straight-chain alkanes 5 C through 10 C, use Greek prefix followed by -ane

  6. Isomerism in alkanes • n-Butane has an isomer (same number and kind atoms, different bonds) • Same molecular formula, different structural formula • Isobutane: branched, all carbons not in a row • CH3(CH3)CHCH3

  7. Isomerism in alkanes • Iso- prefix means branched once • Neo- prefix means branched twice • n-Pentane, isopentane, neopentane • More complex branched alkanes require different naming rules • Any of the straight-chain alkanes can be made into “substitutents” - or branches off a main chain • Methane becomes methyl as a branch (—CH3) • Ethane becomes ethyl as a branch (—CH2CH3), etc

  8. Naming complex branched alkanes • Start by identifying the longest carbon chain • Identify branches off the longest chain as their substituent name (methyl, ethyl, propyl, etc) • Number longest chain starting at end closest to the first branch • Name the compound, starting with branches and indicating the number on the main chain to which the branch is attached

  9. Naming branched alkanes • First identify longest chain (9 carbons) • Number chain starting at end closest to a branch • Identify branches by first numbering them (from main chain number) • 2-methyl, 4-ethyl, 6-methyl • Combine identical branches by saying 2,6-dimethyl • Then give chain name • 4-ethyl, 2,6-dimethyl nonane

  10. Alkenes and alkynes • Alkenes: hydrocarbons with carbon-carbon double bonds • Alkynes: hydrocarbons with carbon-carbon triple bonds • Name by first finding longest carbon chain • Chain name is same as alkane, but end is -ene for double bond, -yne for triple bond • Start numbering on end closest to double/triple bond • Location of multiple bond is given by the smaller numbered carbon involved in the bond

  11. Functional groups • Most organic molecules are simply hydrocarbons with different groups of atoms attached • Functional groups: common groups of atoms found in organic molecules

  12. Common functional groups • Alkyl halide: –X (where X is F, Cl, Br, or I) • Alcohol: –OH • Ether: –O– • Aldehyde: • Ketone: • Carboxylic acid: • Ester: • Amine: –NH2

  13. Alcohols • Alcohols: R–OH • Methanol: CH3OH • Starting material in synthesis of chemical products • Racecar fuel • Highly toxic, causes blindness • Ethanol: CH3CH2OH • Formed by fermentation of glucose • Important gasoline additive

  14. Carboxylic acids • Carboxylic acid: R–COOH • Name by dropping –e from parent hydrocarbon name, and adding –oic acid • CH3COOH: ethanoic acid (acetic acid is common name) • CH3CH2CH2CH2COOH: pentanoic acid

  15. Esters • Esters: RCOOR’ • Formed by reaction of carboxylic acid and alcohol • RCOOH + R’OH  RCOOR’ + H2O • Name by first using alcohol fragment as a fragment name • Then add root of carboxylic acid followed by –ate • Ex. Acetic acid + ethyl alcohol  ethyl acetate

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