Chapter 9 handouts

Chapter 9 handouts - Chapter 9 Alkynes Introduction Alkynes...

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Chapter 9 Alkynes
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Chapter 9 2 Introduction • Alkynes contain a _________ bond. • General formula is _________ • Two elements of unsaturation for each triple bond. • Some reactions are like ________: addition and oxidation. • Some reactions are specific to alkynes.
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Chapter 9 3 Nomenclature: IUPAC • Find the longest chain containing the triple bond. • Change -ane ending to -yne . • Number the chain, starting at the end closest to the triple bond. • Give branches or other substituents a number to locate their position.
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Chapter 9 4 Name these: CH 3 3 2 CCC H 3 3 3 H 2 2 Br 3 CC H
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Chapter 9 5 Additional Functional Groups • All other functional groups, except ethers and halides have a higher priority than alkynes. • For a complete list of naming priorities, look inside the back cover of your text.
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Chapter 9 6 Examples CH 2 CH CH 2 3 CC H 3 CCC H 2 OH 3
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Chapter 9 7 Common Names Named as substituted acetylene. CH 3 CC H 3 3 2 CCC H 3 3
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Chapter 9 8 Physical Properties • Non-polar, insoluble in water. • Soluble in most organic solvents. • Boiling points similar to alkane of same size. • Less dense than water. • Up to 4 carbons, gas at room temperature.
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Chapter 9 9 Acetylene (Ethyne) • Acetylene is used in welding torches. • In pure oxygen, temperature of flame reaches 2800 ° C. • Under high pressure, it would violently decompose to its elements, but the cylinder on the torch contains crushed firebrick wet with acetone to moderate it.
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Chapter 9 10 Synthesis of Acetylene • Heat coke with lime in an electric furnace to form calcium carbide. • Then drip water on the calcium carbide.
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Chapter 9 11 Electronic Structure • The sigma bond is sp-sp overlap. • The two pi bonds are unhybridized p overlaps at 90 ° , which blend into a cylindrical shape of electron density. =>
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Chapter 9 12 Bond Lengths • More s character, so shorter length.
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This note was uploaded on 04/08/2008 for the course CHEM 223 taught by Professor Pearson during the Fall '07 term at Case Western.

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Chapter 9 handouts - Chapter 9 Alkynes Introduction Alkynes...

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