Chapter2_08a

Chapter2_08a - Chapter 2: Organic Compounds: A First Look...

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Chapter 2: Organic Compounds: A First Look Common Bonding Situations Hydrogen 1 bond O H H Carbon 4 bonds (neutral and 8 electrons) C C H H H H H H 4 single bonds C C H H H H double bond C C H H triple bond Reactive Carbon Species C H H H + carbocation C H H H radical C H H H _ carbanion
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Nitrogen 3 bonds and one unshared pair of electrons C N H H H H H C N H H H C N H Other relatively stable species N H H H H + 4 bonds + charge N H H 2 bonds 2 pairs - charge _
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Oxygen 2 bonds and 2 unshared electron pairs C O H H H H C O H H Other relatively stable species O H H H + 3 bonds 1 pair +charge H O _ 1 bond 3 pairs - charge hydronium ion
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Halogens 1 bond and 3 unshared electron pairs C Br H H H also 4 unshared pairs and negative charge Cl _
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Phosphorus three bonds and an unshared pair of electrons (like N) also can have more than 8 electrons in its valence shell Sulfur two bonds and two unshared electron pairs (like O) also can have more than 8 electrons in its valence shell
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Bond Strengths and Bond Lengths Bond Dissociation Energy: energy that must be added to break a bond in a homolytic fashion (one electron with each atom)
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1. Stronger bonds are shorter. 2. C-H, N-H, O-H: 90-110 kcal/mol; 1 (10 -10 m, 100 pm) A o 3. C-C, C-N, C-O: 65-80 kcal/mol; 1.5 A o 4. Bonds become weaker and longer down a column 5. C=C is stronger and shorter than C-C (but not two times) C=O is very strong and very common
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Constitutional Isomers C 2 H 6 O C C O H
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Chapter2_08a - Chapter 2: Organic Compounds: A First Look...

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