HYBRIDIZATION IN CARBON COMPOUNDS!
Chapter 3
“Organic Compounds”
a “single bond”; a “double bond”;
sp3 hybridization sp2 hybridization
a “triple bond”;
sp hybridization
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FUNCTIONAL GROUPS! FUNCTIONAL GROUPS!
A functional group is a part of a larger molecule,
composed of an atom or group of atoms that have a
characteristic chemical behavior.
Alkanes – CnH2n+2 Alkenes – CnH2n
all carbons are sp3 contains one sp2
hybridized hybridized carbon
Alkynes – CnHn a carbon-carbon an —OH group; an oxygen
contains one sp double bond; an alcohol bonded to two
hybridized carbon an alkene carbons;
an ether
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FUNCTIONAL GROUPS! FUNCTIONAL GROUPS!
A functional group is a part of a larger molecule,
composed of an atom or group of atoms that have a only sp3 CH bonds H3 C CH3
Alkane
characteristic chemical behavior.
Alkene C C H2 C CH2
Br
Br2
C C C C
Alkyne C C HC CH
Br C C
Arene C C
a carbon-carbon Stepwise reaction involving a
double bond; Bromonium Ion intermediate C C
an alkene Addition is trans or anti
© ChemistryOnline, 2009-2014 C X H3 C Br© ChemistryOnline, 2009-2014
H3 C CH3
C C H2 C CH2
C OH H3 C OH
C C HC CH C O C H3 C O CH3
C C C OH
C C C NH2 H3 C NH2
C C C O C
FUNCTIONAL GROUPS! FUNCTIONAL GROUPS!
C C N H3 C CN
Halide C X H3 C Br C NH2
O
Nitro C N H3 C NO2
Alcohol C C ON
C OH H3 C OH
C S C O H3H
C CO SH
CH3
Ether Thiol CC NSH 3
C O C H3 C O CH3
O
Amine Sulfide C S C H!3C! S! CH!3!
C NH2 H3 C NH2 !
O
O
H3 C C H
C C H
Nitrile C C N H3 C CN O
O
O H3 C C CH3
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C N H3 C NO2
O
O O
H3 C C OH
C C OH
C S C H3 C O CH3 O
O
H3 C C OCH3
C C O C
C SH H3 C SH
FUNCTIONAL GROUPS! O FUNCTIONAL GROUPS! O
Carbonyl Compounds C Carbonyl Compounds C
O O O O
Aldehyde C C H H3 C C H Amide C C NH2 H3 C C NH2
O O
O O
Ketone C C C H3 C C CH3
Acid Halide C C Cl H3 C C Cl
O O
Carboxylic Acid C C OH H3 C C OH
O O O O
O O Carboxylic Acid
C C O C C H3 C C O C CH3
Ester H3 C C OCH3 Anhydride
C C O C
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THE REPRESENTATION OF CARBON COMPOUNDS! THE REPRESENTATION OF CARBON COMPOUNDS!
As you draw these structures you should note that
rotation around single bonds in produces Conformational isomers,
compounds which differ in their spatial geometry... all of which have a one-
carbon chain attached to
the central carbon of a five-
carbon chain.
...these are referred to as Conformational Isomers.
Because rotation around single bonds is rapid (≈106
sec-1), conformational isomers can not typically be
separated and conformational isomers of a
compound are all regarded as identical forms.
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ISOMERISM IN CARBON COMPOUNDS! IN-CLASS PROBLEM!
Write all of the constitutional isomers having the
Compounds having the same number and types of molecular formula C3H8
atoms, but which differ in the way those atoms are
connected are referred to as Constitutional
Isomers.
C7H16 C7H16
Constitutional isomers are different chemical
compounds, and can be separated by standard
methods.
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IN-CLASS PROBLEM! IN-CLASS PROBLEM!
Write all of the constitutional isomers having the Write all of the constitutional isomers having the
molecular formula C3H6 molecular formula C4H8
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IN-CLASS PROBLEM! IN-CLASS PROBLEM!
Write all of the constitutional isomers having the Write all of the constitutional isomers having the
molecular formula C2H6O molecular formula C3H6O2
O H
O
O O
H O H OH
O O
O
O O O
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IN-CLASS PROBLEM! IN-CLASS PROBLEM!
Write all of the constitutional isomers having the Are the two compounds shown below identical,
molecular formula C3H6O2 constitutional isomers or different chemical compounds
and not isomeric?
OH O O OH
O O
O
O CH2 CH2
OH
O
O
O OH
O
H3 C CH2 CH3 and
O O
O
O O O
HO
OH
O O
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IN-CLASS PROBLEM! IN-CLASS PROBLEM!
Are the two compounds shown below identical, Are the two compounds shown below identical,
constitutional isomers or different chemical compounds constitutional isomers or different chemical compounds
and not isomeric? and not isomeric?
Cl H
CH3 CH2 CH2 CHClCH3 CH3 CH2 C and
CH and C H
Cl
Cl CH3
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IN-CLASS PROBLEM! IN-CLASS PROBLEM!
Are the two compounds shown below identical, Are the two compounds shown below identical,
constitutional isomers or different chemical compounds constitutional isomers or different chemical compounds
and not isomeric? and not isomeric?
O O
Cl
ClCH2 C C H H3 C C H
H and CH NHCH3 and N
CH3 CH3
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IN-CLASS PROBLEM! NOMENCLATURE OF ALKANES!
Are the two compounds shown below identical, The name of an alkane is simply based on the number of
constitutional isomers or different chemical compounds carbons in the longest continuous chain; this is called
and not isomeric? the parent chain. The suffix ane is then added to show it
is an alkane.
and
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NOMENCLATURE OF ALKANES! NOMENCLATURE OF ALKANES!
An alkyl group is formed by removing one hydrogen from An alkyl group is formed by removing one hydrogen from
the parent chain. the parent chain.
• Often abbreviated as “R” (for Radical) • Often abbreviated as “R” (for Radical)
• An alkyl group is named by replacing –ane with –yl • An alkyl group is named by replacing –ane with –yl
• -CH3 is “methyl” (from methane) • -CH3 is “methyl” (from methane)
• -CH2CH3 is “ethyl” (from ethane) • -CH2CH3 is “ethyl” (from ethane)
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TYPES OF ALKYL GROUPS! TYPES OF ALKYL GROUPS!
An alkyl group can also be named based on its An alkyl group can also be named based on its
connection site in the chain. connection site in the chain.
a carbon at the end of a chain (primary alkyl group)! a carbon at the end of a chain (primary alkyl group)!
a carbon in the middle of a chain (secondary alkyl a carbon in the middle of a chain (secondary alkyl
group)! group)!
a carbon with three carbons attached to it (tertiary a carbon with three carbons attached to it (tertiary
alkyl group)! alkyl group)!
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IUPAC NOMENCLATURE OF BRANCHED ALKANES! IUPAC NOMENCLATURE OF BRANCHED ALKANES!
1. The name of a branched alkane is based on the 2. Number the atoms in the chain, beginning at the
number of carbons in the longest continuous chain. end nearer the first substituent on the chain. If
there are substituents occurring at equal distances
from both ends of the chain, begin numbering at
the end providing the lowest number sequence at
the first point of difference. When two equal chains
compete for selection as base chain, choose the
one with the greatest number of substituents.
Indicate the longest continuous carbon
chains in the molecules shown above.
Indicate the longest continuous carbon
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chains in the molecules shown above. © ChemistryOnline, 2009-2014
IUPAC NOMENCLATURE OF BRANCHED ALKANES! IUPAC NOMENCLATURE OF BRANCHED ALKANES!
3. Substituents on the chain are named as alkyl 4. Complex substituents are numbered from the point
radicals and are numbered using the numbering of attachment to the main chain and are included in
system from (2). When two or more substituents parenthesis.
are identical, use the multipliers: di-, tri-, tetra-, etc.
Names are to be arranged alphabetically without
regard for these multiplier prefixes. Write the name
as a single word, using hyphens to separate
prefixes and commas to separate numbers.
Indicate and number the longest continuous
Indicate and number the longest continuous carbon chains in the molecule shown above.
carbon chains in the molecule shown above. © ChemistryOnline, 2009-2014 © ChemistryOnline, 2009-2014
IUPAC NOMENCLATURE OF BRANCHED ALKANES! IUPAC NOMENCLATURE OF BRANCHED ALKANES!
5. Complex substituents are sometimes named using 5. Complex substituents are sometimes named using
common names: common names:
CH3 CH3
CH isopropyl CH CH2 isobutyl
1
CH3 CH3 10
2,3-dimethyl
6-(2-methylpropyl)
CH3 or 6-isobutyl
CH3
CH sec-butyl CH3 C tert-butyl
2,3-dimethyl-6-(2-methylpropyl)decane
CH3 CH2 CH3 or 6-isobutyl-2,3-dimethyldecane
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IUPAC NOMENCLATURE OF BRANCHED ALKANES! IUPAC NOMENCLATURE OF BRANCHED ALKANES!
H H CH2 Cl
6. Halogens on an alkyl chain are simply treated as a Provide an acceptable IUPAC name for the following:
substituent and are named using “chloro”,
H CH3
“bromo”, “iodo” or “fluoro” as the substituent
H HCH CH Cl
name, following the usual rules. 2 23
H CH3
H3 CH CHC CH3
H 2 CH3
8 CH CHH 2 ClCH Cl
H 2
CH
H ClCH3 3
H3 C H C CH3 3CH
1 Cl! CH2 CH3
CH2 CHH23 Cl
ClCH
3
CHH
CH 33
H3 C C CH 3
CH
H3 C C H CH3
CH CH
CH 2 Cl
3
© ChemistryOnline, 2009-2014 Cl CH2 Cl © ChemistryOnline, 2009-2014
Cl H
CH3
CH3
CH H3
H
H
H
CH3
CH3
CONFORMATIONAL ISOMERS OF ETHANE! CONFORMATIONAL ISOMERS OF ETHANE!
Eclipsed Staggered Eclipsed Staggered
As the carbons in ethane undergo rotation, the
hydrogens move from an arrangement in which they are
eclipsed to one in which they are staggered, relative to
each other. These two conformations have slightly
different energies.
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CONFORMATIONAL ISOMERS OF BUTANE! CONFORMATIONAL ISOMERS OF BUTANE!
120o
60o rotation
rotation
240o
180o 300o
rotation
rotation rotation
“Newman-like” view
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CONFORMATIONAL ISOMERS OF BUTANE! IN-CLASS PROBLEM!
eclipsed
Draw structures for the following:
eclipsed eclipsed
gauche gauche
6-ethyl-4-isopropyldecane
6-ethyl-4-(1-methylethyl)decane
2-fluoro-3-methylpentane
4-(2,2-dibromoethyl)-3,5-dichloroheptane
anti gauche gauche anti
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IN-CLASS PROBLEM! IN-CLASS PROBLEM!
Draw a Newman projection of the anti and gauche Name the following hydrocarbon:
conformation of 1,2-dichloroethane. Which is most
stable?
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