Chapter 9 - Wade(1)

Chapter 9 - Wade(1) - Introduction to General and Organic...

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Chapter 9 Alkynes Dr. David P. Brown Department of Chemistry Introduction to General and Organic Chemistry III
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Chapter 9 2 Introduction Alkynes contain the triple bond . General formula is C n H 2n-2 Also known as Acetylenes Two elements of unsaturation for each triple bond. Some reactions are like alkenes: 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 Examples: CH 3 CH CH 3 CH 2 C C CH CH 3 CH 3 CH 3 C C CH 2 CH 2 Br CH 3 C CH
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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 CH CH 3 C CH CH 3 C C CH 2 CH OH CH 3 H 3 C C C CH CH 3 OEt
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Chapter 9 7 Common Names Named as substituted acetylene . CH 3 C CH CH 3 CH CH 3 CH 2 C C CH CH 3 CH 3
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Chapter 9 8 Physical Properties Nonpolar , 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 Bond Lengths More s character, so shorter length . Three bonding overlaps, so shorter. Bond angle is 180 ° , so linear geometry . =>
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10 Acidity of Alkynes Terminal alkynes, R-C C-H , are more acidic than other hydrocarbons. Acetylene can be deprotonated by NH 2 - to form the acetylide ion , but not by OH - or RO - . More
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This note was uploaded on 09/04/2011 for the course CHE 1130 taught by Professor Brown during the Fall '08 term at St. Johns Duplicate.

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Chapter 9 - Wade(1) - Introduction to General and Organic...

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