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chapter 7 - Start of chapter 7 lecture notes Alkenes are...

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Start of chapter 7 lecture notes
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Alkenes are unsaturated For a given molecular formula you can determine the number of elements of unsaturation a C=C or a ring structure leads to unsaturation # of elements of unsaturation = ½(2C + 2-H) C = number of C atoms H = number of H atoms How do I account for atoms that are not C or H? Ignore O count a halogen as a H count a N as ½ a C Caffeine: C 8 H 10 N 4 O 2 Cholesterol: C 27 H 46 O # elements of unsat’n: 6 # elements of unsat’n: 5 The degree of unsaturation is the number of multiple bonds &/or rings in a structure Or subtract the # of N from the # of H
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N N HO Determine the degree of unsaturation for the following molecules 3 rings + 9 Pi bonds = 12 You can check using the molecular formula C 16 H 12 N 2 O HOOC 1 ring + 3 Pi bonds = 4 C 11 H 16 O 2
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Naming alkenes 1. Find longest continuous C chain with most possible C-C double bonds 1. Number the C chain – starting at the end closest to a C=C in a ring C1 and C2 are C’s in a C=C 1. Name all substituents Alkenes as substituents: R=CH 2 Methylene R-CH=CH 2 vinyl (ethenyl) R-CH 2 -CH=CH 2 allyl (2-propenyl) 1. Organize multiple C=C (&/or substituents) 2 C=C is diene 3 C=C is triene 4 C=C is tetraene
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Ocimene – a plant oil 1,3,6-octatriene 3,7-dimethyl IUPAC name: Or 3,7-dimethylocta-1,3,6-triene 2,3-dimethylcyclopentene Name the following molecules using the IUPAC naming system
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Pi bond characteristics Pi bonds do NOT freely rotate like single bonds do This means that the orientation of groups in relation to the Pi bond matters Net dipole = 0 Net dipole > 0
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