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Organic Chemistry Oxygen and Sulfur in Organic Compounds

Organic Chemistry Oxygen and Sulfur in Organic Compounds. Chapter 12 Part 05 Thiols. Page 102. H. R. S. S. H. H. 1. Thiols - contain the sulfhydryl or mercapto functional group, -SH - general formula RSH

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Organic Chemistry Oxygen and Sulfur in Organic Compounds

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  1. Organic Chemistry Oxygen and Sulfurin Organic Compounds

  2. Chapter 12Part 05Thiols Page 102

  3. H R S S H H 1. Thiols -contain the sulfhydryl or mercapto functional group, -SH - general formula RSH - derivatives of hydrogen sulfide gas where one H is replaced by an R group

  4. 2. Nomenclature of Thiols -determine main chain (longest continuous chain of C atoms that contains the –SH). Keep the entire name; don’t remove any letters - add the suffix –thiol - If two thiol groups – dithiol - If three thiol groups – trithiol - number the chain to give the C bearing the –SH the lowest possible number - place this number in front of the name of the thiol, separated by a hyphen - if branched chain, always number giving the - SH group priority and name the substituents like you would for any other organic compound (lowest numbers, alphabetical, etc.)

  5. H H H H C C H C SH C H H H H 2. Nomenclature Name the following thiol. 1-butanethiol

  6. H H H H C C H C H C H H H SH 2. Nomenclature Name the following thiol. 2-butanethiol

  7. H SH H H H C C H C H C C H H SH H H 2. Nomenclature Name the following thiol. 1,1-pentanedithiol

  8. H H H Br SH H C C C H C H C C H H H H H H 2. Nomenclature Name the following thiol. 4-bromo-3-hexanethiol

  9. SH H2N 2. Nomenclature Name the following thiol. trans-3-amino-1-cyclopentanethiol

  10. SH SH 3. Nomenclature Name the following thiol. cis-1,2-cyclohexanedithiol

  11. 3. Thiols -hydrogen sulfide gas smells like rotten eggs - thiols have offensive odors - Examples 1-propanethiol (found in onions & garlic – makes eyes tear (lachrimator)) 3-methyl-1-butanethiol & trans-2-butene-1-thiol (found in skunk urine) 2-chloroethylsulfide (mustard gas)

  12. 3. Thiols methanethiol & ethanethiol - added to odorless natural gas after the New London, Texas gas explosion in 1937 http://www.youtube.com/watch?v=ZqCRNtZ12mo&playnext=1&list=PL0BAC9A84ED0009A7

  13. 3. Thiols -important in biochemistry - two –SH groups can be oxidized (hydrogens removed between them) to form disulfide linkages (hold protein chains together) - helps to determine the shapes of protein molecules

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