Organic Chemistry Oxygen and Sulfur in Organic Compounds

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Organic Chemistry Oxygen
and Sulfurin Organic Compounds
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Chapter 12Part 05Thiols
Page 102
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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
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2. Nomenclature of Thiols - determine main chain
(longest continuous chain of C atoms that
contains the SH). Keep the entire name dont
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.)
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2. Nomenclature Name the following thiol.
1-butanethiol
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2. Nomenclature Name the following thiol.
2-butanethiol
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2. Nomenclature Name the following thiol.
1,1-pentanedithiol
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2. Nomenclature Name the following thiol.
4-bromo-3-hexanethiol
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2. Nomenclature Name the following thiol.
trans-3-amino-1-cyclopentanethiol
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3. Nomenclature Name the following thiol.
cis-1,2-cyclohexanedithiol
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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)
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3. Thiols methanethiol ethanethiol - add
ed to odorless natural gas after the New London,
Texas gas explosion in 1937
http//www.youtube.com/watch?vZqCRNtZ12moplaynex
t1listPL0BAC9A84ED0009A7
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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