Download Lecture CH14 chem131pikul

Follow Up Questions from Chapter 13: Natural Polymers
Natural Latex Rubber
Natural precursor
Industrial precursor
Spider Silk
Cellulose
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CHAPTER 14: Oxygen, Halogen, & Sulfur
Learning Objectives:
! Name organic compounds with carbon-heteroatom single
bonds (oxygen, halogens, sulfur)
! Identify ?@'(<@'(:@(%&,/1/&3(%#=(%&85&(1%&+="3(
! A$"=+,4(41"(B$/=C,43(/$($"%,4%#43(D/$(D/&&/E+#*($"%,F/#3G(
! H&,/1/&(="15=$%F/#(
! H&,/1/&(/I+=%F/#(
! 9C&DC$(/I+=%F/#((
! 9C&DC$($"=C,F/#(
(
:(
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Functional
Groups
Overview
Alkyl
halides
Single Bond
to a
Heteroatom
Functional
Groups
Alcohols
Ethers
Thiols
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J(
Alcohols
& Alkyl
Halides
?@'(<@'(:@(
Alcohols
Nomenclature
#
)M(
K(
J(
<(
?(
B$"QI( R(
:(
O(
B%$"#4( R(
3CPI(
B$"QI(
S+$34(*+T"(&/,%F/#(%#=(45B"(/D(3CL3F4C"#43(
9",/#=(*+T"(&/,%F/#(/D(=/CL&"(L/#=(
B%$"#4(
M/E(2%#5(,%$L/#3(+#(&/#*"34(,1%+#U(
3CPI(
M/E(2%#5(/D(41"(DC#,F/#%&(*$/CB(%#=(
E1%4(+3(+4U(H&,/1/&(V(W/&X(
<N2"415&(JN( 1"I%#( /&(
1
2
3
4
5
6
7
8
9
10
Greek 7;:2<.=;(!=2<0(
Root #3>20/(?2@/(
meth
2"41%#"(
eth
"41%#"(
prop
B$/B%#"(
but
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pent
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hex
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non
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:(
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0M:0M<0M<0M<N(
LC45&(
O(
0M:0M<0M<0M<0M<N(
B"#45&(
K(
0M:0M<0M<0M<0M<0M<N(
1"I5&(
YZ/4"G(%["$(41"(*$""8($//4(/D(41"(B%$"#4(C3"(W%#X'(+"(1"I20(
Y(9",/#=(Z/4"G(E1"#(E"(1%T"(2/$"(41"#(?(2C&FB&"(L/#=(41"(B%$"#4(#%2"(1%3(%#(W%X(%["$(41"(*$""8($//4G(1"I2( K(
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Functional
Groups
Alcohols
Fermentation
\(
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Rxns of
Alcohols
Elimination Reaction: Dehydration
Zaitsev Rule:
The major product in
elimination is the
alkene that has more
alkyl groups bonded
to it.
Rxns of
Alcohols
Oxidations
Oxidation requires breaking C-H bonds and forming new C-O bonds. When
alcohol is the starting material the products always have a carbonyl group.
Rxns of
Alcohols
Alcohol Metabolism
S+#=(#/4"3(D$/2(%$41C$]3("IB&%+#%F/#((
Ethers
Nomenclature
#
?(
)(
B$"QI( R(
B$"QI(
J(
<(
:(
B%$"#4( R(
3CPI(
^3"(%&85&(3CL3F4C4%#4(#%2+#*($//43'(LC4(=$/B(
41"(W5&X(%#=(C3"(W/I5X(D/$(41"(3+2B&"34(%&85&(
*$/CB(L/#="=(4/(41"("41"$(/I5*"#;(
B%$"#4(
M/E(2%#5(,%$L/#3(+#(&/#*"34(,1%+#U(
3CPI(
^3"(%&8%#"("#=+#*G(%#"((
<N"41/I5( LC4( %#"(
1
2
3
4
5
6
7
8
9
10
Greek 7;:2<.=;(!=2<0(
Root #3>20/(?2@/(
meth
2"41%#"(
eth
"41%#"(
prop
B$/B%#"(
but
LC4%#"(
pent
B"#4%#"(
hex
1"I%#"(
hept
1"B4%#"(
oct
/,4%#"(
non
#/#%#"(
dec
=",%#"(
A(
#3>-3(D:48E(
!2:B405(
?2@/(
7;:8C;8:/(
?(
0M:N(
2"415&(
<(
0M:0M<N(
"415&(
:(
0M:0M<0M<N(
B$/B5&(
J(
0M:0M<0M<0M<N(
LC45&(
O(
0M:0M<0M<0M<0M<N(
B"#45&(
K(
0M:0M<0M<0M<0M<0M<N(
1"I5&(
??(
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Functional
Groups
Ethers
Diethyl Ether
The first anesthetic administered
in 1842 by Crawford Long
Heterocycles
)(
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?<(
Thiols
Nomenclature
#
9M(
<(
J(
O(
:(
B$"QI( R(
B%$"#4( R(
?(
3CPI(
B$"QI(
!+T"(&/,%F/#(%#=(45B"(/D(3CL3F4C"#43'(41"#(
*+T"(&/,%F/#(/D(41+/&(*$/CB;(
B%$"#4(
M/E(2%#5(,%$L/#3(+#(&/#*"34(,1%+#U(
3CPI(
M5=$/,%$L/#(DC#,F/#%&(*$/CB(3CPI((
R(W41+/&X(
<'JN=+2"415&(?N( 1"B4( %#"41+/&(
1
2
3
4
5
6
7
8
9
10
Greek 7;:2<.=;(!=2<0(
Root #3>20/(?2@/(
meth
2"41%#"(
eth
"41%#"(
prop
B$/B%#"(
but
LC4%#"(
pent
B"#4%#"(
hex
1"I%#"(
hept
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oct
/,4%#"(
non
#/#%#"(
dec
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A(
#3>-3(D:48E(
!2:B405(
?2@/(
7;:8C;8:/(
?(
0M:N(
2"415&(
<(
0M:0M<N(
"415&(
:(
0M:0M<0M<N(
B$/B5&(
J(
0M:0M<0M<0M<N(
LC45&(
O(
0M:0M<0M<0M<0M<N(
B"#45&(
K(
0M:0M<0M<0M<0M<0M<N(
1"I5&(
?:(
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Functional
Groups
Thiols
Insulin
6"%#NA1+&+BB"(0%$4%+&&"$'(A1;_;(`1"(."4%(0"&&(0/#3/$FC2((
92+41;(!"#"$%&()$*%#+,(-(.+/&/,+%&(01"2+34$5(<#=(>=;(
?J(
Rxns of
Thiols
Oxidation & Reduction
Alkyl Halides
Nomenclature
#
?(
<(
0&(
:(
B$"QI( R(
B$"QI(
J(
B%$"#4( R(
K(
O(
3CPI(
!+T"(&/,%F/#(%#=(45B"(/D(3CL3F4C"#43;(
a"B&%,"(W+#"X(+#(1%&+="(#%2"(E+41(W/X'(+"(
01&/$+#"(V(,1&/$/((
B%$"#4(
M/E(2%#5(,%$L/#3(+#(&/#*"34(,1%+#U(
3CPI(
b1%4(+3(41"(15=$/,%$L/#(DC#,F/#%&(
*$/CBU(cD(%&8%#"(41"#(W%#"X(3CPI(
<N,1&/$/(JN2"415&(( 1"I( %#"(
1
2
3
4
5
6
7
8
9
10
Greek 7;:2<.=;(!=2<0(
Root #3>20/(?2@/(
meth
2"41%#"(
eth
"41%#"(
prop
B$/B%#"(
but
LC4%#"(
pent
B"#4%#"(
hex
1"I%#"(
hept
1"B4%#"(
oct
/,4%#"(
non
#/#%#"(
dec
=",%#"(
A(
#3>-3(D:48E(
!2:B405(
?2@/(
7;:8C;8:/(
?(
0M:N(
2"415&(
<(
0M:0M<N(
"415&(
:(
0M:0M<0M<N(
B$/B5&(
J(
0M:0M<0M<0M<N(
LC45&(
O(
0M:0M<0M<0M<0M<N(
B"#45&(
K(
0M:0M<0M<0M<0M<0M<N(
1"I5&(
?K(
92+41;(!"#"$%&()$*%#+,(-(.+/&/,+%&(01"2+34$5(<#=(>=;(
Functional
Groups
Alkyl Halides
Rxns of Alkyl
Halides
Substitution Reactions with Alkyl Halides
Substitution Reactions at 1° Carbons
Halides (Cl, Br) are good leaving groups (L) because they form very
polar covalent bonds with carbon.
Nucleophiles (Nu-) include negatively charged molecules or amines
(RNH2). Common Nucleophiles: NaOH ( OH-), NH3, RS-, I-.
Rxns of Alkyl
Halides
Substitution Reactions
Substitution Reactions at 1° Carbons
Substitution Reactions at 3° Carbons
Rxns of Alkyl
Halides
Substitution Reactions