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Organic Compounds: Alkanes and Their Stereochemistry: Based On Mcmurry'S Organic Chemistry, 7 Edition

1) Alkanes are unreactive hydrocarbons containing only carbon-carbon single bonds and carbon-hydrogen bonds. This chapter introduces alkanes and uses them to discuss naming organic compounds and stereochemistry. 2) Functional groups are collections of atoms that confer characteristic reactivity to molecules. Common functional groups include alkenes, alkynes, aromatics, alcohols, carbonyls, and others. 3) Alkane isomers can differ in carbon chain structure and branching. Naming involves identifying the parent chain and substituents. Steric effects influence alkane conformations, with staggered configurations generally most stable.

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34 views

Organic Compounds: Alkanes and Their Stereochemistry: Based On Mcmurry'S Organic Chemistry, 7 Edition

1) Alkanes are unreactive hydrocarbons containing only carbon-carbon single bonds and carbon-hydrogen bonds. This chapter introduces alkanes and uses them to discuss naming organic compounds and stereochemistry. 2) Functional groups are collections of atoms that confer characteristic reactivity to molecules. Common functional groups include alkenes, alkynes, aromatics, alcohols, carbonyls, and others. 3) Alkane isomers can differ in carbon chain structure and branching. Naming involves identifying the parent chain and substituents. Steric effects influence alkane conformations, with staggered configurations generally most stable.

Uploaded by

Lois Eunice
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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3.

Organic Compounds:
Alkanes and Their
Stereochemistry

Based on McMurry’s Organic Chemistry, 7th edition


Why this Chapter
 Alkanes are unreactive, but provide useful vehicle to
introduce important ideas about organic compounds

 Alkanes will be used to discuss basic approaches to naming


organic compounds

 We will take an initial look at 3-D aspects of molecules

2
3.1 Functional Groups
 Functional group -
collection of atoms at a site
that have a characteristic
behavior in all molecules
where it occurs

 The group reacts in a typical


way, generally independent
of the rest of the molecule

 For example, the double


bonds in simple and
complex alkenes react with
bromine in the same way
3
Functional Groups with Multiple
Carbon–Carbon Bonds
 Alkenes have a C-C
double bond
 Alkynes have a C-C
triple bond
 Arenes have special
bonds that are
represented as
alternating single
and double C-C
bonds in a six-
membered ring

4
Functional Groups with Carbon Singly
Bonded to an Electronegative Atom

5
Groups with a Carbon–Oxygen Double Bond
(Carbonyl Groups)

6
Survey of Functional Groups

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Survey of Functional Groups

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3.2 Alkanes and Alkane Isomers
 Alkanes: Compounds with C-C single bonds and C-H
bonds only (no functional groups)
 Connecting carbons can lead to large or small molecules
 The formula for an alkane with no rings in it must be
CnH2n+2 where the number of C’s is n
 Alkanes are saturated with hydrogen (no more can be
added
 They are also called aliphatic compounds

9
Alkane Isomers
 CH4 = methane, C2H6 = ethane, C3H8= propane
 The molecular formula of an alkane with more than
three carbons can give more than one structure
 C4 (butane) = butane and isobutane
 C5 (pentane) = pentane, 2-methylbutane, and 2,2-
dimethylpropane
 Alkanes with C’s connected to no more than 2 other
C’s are straight-chain or normal alkanes
 Alkanes with one or more C’s connected to 3 or 4 C’s
are branched-chain alkanes

10
Constitutional Isomers
 Isomers that differ in how their atoms are arranged in chains are
called constitutional isomers
 Compounds other than alkanes can be constitutional isomers
of one another
 They must have the same molecular formula to be isomers

11
Condensed Structures of Alkanes
 We can represent an alkane in a brief form or in
many types of extended form
 A condensed structure does not show bonds but lists
atoms, such as
 CH3CH2CH2CH3 (butane)
 CH3(CH2)2CH3 (butane)

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3.3 Alkyl Groups
 Alkyl group – remove
one H from an alkane (a
part of a structure)
 General abbreviation “R”
(for Radical, an
incomplete species or the
“rest” of the molecule)
 Name: replace -ane
ending of alkane with -yl
ending
 CH3 is “methyl” (from
methane)
 CH2CH3 is “ethyl”
from ethane
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Types of Alkyl groups
 Classified by the connection site (See Figure 3.3)
 a carbon at the end of a chain (primary alkyl group)
 a carbon in the middle of a chain (secondary alkyl
group)
 a carbon with three carbons attached to it (tertiary alkyl
group)

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3.4 Naming Alkanes
 Compounds are given systematic names by a process that uses

 Follows specific rules


 Find parent hydrocarbon chain
 Carbons in that main chain are numbered in sequence
 Substituents are identified numbered
 Write compound name is single word
 Name a complex substituents as though it were a compound
itself
 See specific examples in text
 Try ThomsonNow Organic Interactive from p. 90 of
your text
18
3.5 Properties of Alkanes
 Called paraffins (low affinity compounds)
because they do not react as most chemicals
 They will burn in a flame, producing carbon
dioxide, water, and heat
 They react with Cl2 in the presence of light to
replace H’s with Cl’s (not controlled)

19
Physical Properties
 Boiling points and melting points increase as size of alkane
increases
 Dispersion forces increase as molecule size increases, resulting in
higher melting and boiling points

20
3.6 Conformations of Ethane
 Stereochemistry concerned with the 3-D
aspects of molecules
  bonds are cylindrically symmetrical
 Rotation is possible around C-C bonds in
open-chain molecules

21
Conformers
 Conformation- Different arrangement of
atoms resulting from bond rotation
 Conformations can be represented in 2 ways:

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Torsional Strain
 We do not observe perfectly free rotation
 There is a barrier to rotation, and some
conformers are more stable than others
 Staggered- most stable: all 6 C-H bonds are
as far away as possible
 Eclipsed- least stable: all 6 C-H bonds are as
close as possible to each other

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3.7 Conformations of Other
Alkanes
 The eclipsed conformer of propane has 3
interactions: two ethane-type H-H interactions, and
one H-CH3 interaction

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Conformations of Other Alkanes

• Conformational situation is more complex for larger alkanes


• Not all staggered conformations has same energy, and not all
eclipsed conformations have same energy

26
Conformations of Butane
 Anti conformation- methyl groups are 180˚ apart
 Gauche conformation- methyl groups are 60˚ apart

Which is the most energetically stable?

27
Steric Strain
 Steric strain- repulsive interaction occurring between atoms
that are forced closer together than their atomic radii allow

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