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2.5 Isomerism in alkenes

2.5 Isomerism in alkenes. C 2 H 4. open-chain (linear and branched) and cyclic Generic formula: Start with C n H 2n+2 and minus two for each C=C one C=C  C n H 2n e.g., C 2 H 4. 3 kinds of isomerism. Constitutional (structural) isomerism Structural – C=C or ring

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2.5 Isomerism in alkenes

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  1. 2.5 Isomerism in alkenes

  2. C2H4 • open-chain (linear and branched) and cyclic • Generic formula: Start with CnH2n+2 and minus two for each C=C • one C=C  CnH2n e.g., C2H4

  3. 3 kinds of isomerism • Constitutional (structural) isomerism • Structural – C=C or ring • Skeletal – C atoms connected in a different order • Positional - The location of C=C varies but the C skeleton remains unchanged • Stereoisomerism (geometric isomerism)Because of the rigidity of C=C there can be cis-trans isomerism in alkenes.

  4. Constitutional isomerism (cont.) Structural isomers  C=C or ring • One C=C  CnH2n e.g., C3H6 or • One ring

  5. CnH2n-2 Alkenes & cyclic alkanes are constitutional isomers

  6. Constitutional isomerism (cont.) • Positional - The location of C=C varies but the C skeleton remains unchanged

  7. Constitutional isomerism (cont.) • Skeletal – C atoms connected in a different order

  8. cis AND trans ISOMERS

  9. C C C H C C C C C H H H The atoms attached to the C=C are locked in place Because there is no rotation about a carbon-carbon bond THIS GIVES STEREO or SKELETAL ISOMERS

  10. C C C H C C C C C H H H CIS/TRANS ISOMERS substituents on the same side of main chain substituents on opposite sides of main chain cis trans

  11. COMPARE cis / trans ISOMERS IN RING COMPOUNDS cis trans In alkenes and rings cis / trans isomersare called stereoisomers or geometric isomers.

  12. H C C H C H C H H H H 3 3 2 3 H C H C H H C H H C H C H 2 3 3 2 3 TWO IDENTICAL SUBSTITUENTS RULE: A C=C at the end of a chain cannot be cis/trans

  13. H C H C H 3 3 H H C 3 C H C H C H 3 2 3 H C C H H C C H C H C H H H H 3 3 3 3 2 3 H C H C H H C H H C H C H 2 3 3 2 3 RULE: If there are two identical substituents on one of the double-bond-carbons, cis / trans is not possible.

  14. NAMING cis / trans ISOMERS OF ALKENES main chain crosses to other side of double bond = trans main chain stays on same side of double bond = cis ZIG-ZAG cis-3-hexene trans-3-hexene notice that these prefixes are in italics

  15. This compound is cis Although the two methyl groups are trans to each otherthey don’t determine the name of the compound. Be Careful !!! The longest chain determines cis / trans in the IUPAC name NOT THE LOCATION OF THE METHYL GROUPS cis-3-methyl-2-pentene trans-3-methyl-2-pentene This compound is trans Although the two methyl groups are cis to each otherthey don’t determine the name of the compound.

  16. MORE THAN ONE DOUBLE BOND DIENES , etc.

  17. DIENES AND POLYENES Hexadiene trans, trans trans, cis trans,trans-2,4-hexadiene trans,cis-2,4-hexadiene cis,cis-2,4-hexadiene cis,trans-2,4-hexadiene identical cis, cis cis, trans

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