Chapter5 - Organic Chemistry CHE 275 Chapter 5 Structure...

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Unformatted text preview: Organic Chemistry CHE 275 Chapter 5 Structure and Preparation of Alkenes: Elimination Reactions Alkenes are hydrocarbons that contain a carbon-carbon double bond also called "olefins" characterized by molecular formula C n H 2n said to be "unsaturated" Alkenes H 2 C CH 2 H 2 C CHCH 3 Ethene or Ethylene (both are acceptable IUPAC names) Propene (Propylene is sometimes used but is not an acceptable IUPAC name) Alkene Nomenclature 1) Find the longest continuous chain that includes the double bond. 2) This is the parent chain (butane in this case) 3) Replace the - ane ending of the unbranched alkane having the same number of carbons by - ene . 4) Number the chain in the direction that gives the lowest number to the doubly bonded carbon nearest the end of the chain. H 2 C CHCH 2 CH 3 1-Butene 1979 IUPAC Alkene Nomenclature 5) If a substituent is present, identify its position by number. The double bond takes precedence over alkyl groups and halogens when the chain is numbered. The compound shown above is 4-bromo-3-methyl-1-butene. H 2 C CHCHCH 2 Br CH 3 1979 IUPAC Alkene Nomenclature 6) If a substituent is present, identify its position by number. Hydroxyl groups take precedence over the double bond when the chain is numbered. The compound shown above is 2-methyl-3-buten-1-ol. H 2 C CHCHCH 2 OH CH 3 1979 IUPAC Alkene Nomenclature 1) Find the longest continuous chain that includes the double bond. 2) This is the root chain, butane in this case, so But- is the root name 3) Number the chain in the direction that gives the lowest number to the doubly bonded carbon nearest the end of the chain. 4) This gives the locant of the alkene, 1- 5) Functional group is an alkene, so suffix is ene H 2 C CHCH 2 CH 3 But-1-ene 2004 IUPAC Alkene Nomenclature 5) If a substituent is present, identify its position by number. The double bond takes precedence over alkyl groups and halogens when the chain is numbered. The compound shown above is 4-bromo-3-methyl-but-1-ene. H 2 C CHCHCH 2 Br CH 3 2004 IUPAC Alkene Nomenclature 6) If a substituent is present, identify its position by number. Hydroxyl groups take precedence over the double bond when the chain is numbered. The compound shown above is 2-methylbut-3-en-1-ol. H 2 C CHCHCH 2 OH CH 3 2004 IUPAC Alkene Nomenclature methylene vinyl allyl isopropenyl CH H 2 C H 2 C CHCH 2 H 2 C CCH 3 H 2 C Alkene Nomenclature 1) Replace the -ane ending of the cycloalkane having the same number of carbons by -ene. Cyclohexene Cycloalkene Nomenclature 1) Replace the - ane ending of the cycloalkane having the same number of carbons by - ene . 2) Number through the double bond in the direction that gives the lower number to the first-appearing substituent....
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Chapter5 - Organic Chemistry CHE 275 Chapter 5 Structure...

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