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4.5 Lecture

The document discusses different types of isomers in organic compounds including structural isomers, conformational isomers, and branched-chain alkanes. It also covers rules for systematically naming organic compounds using IUPAC nomenclature.

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KhalidA
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34 views18 pages

4.5 Lecture

The document discusses different types of isomers in organic compounds including structural isomers, conformational isomers, and branched-chain alkanes. It also covers rules for systematically naming organic compounds using IUPAC nomenclature.

Uploaded by

KhalidA
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPT, PDF, TXT or read online on Scribd
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4.

5 Isomerism in Organic Compounds, Part 1


Structural Isomers
Structural isomers are compounds with the
same molecular formula but a different
connectivity.
Butane, a four-carbon molecule, is the simplest
alkane that has two structural isomers.

2011 Pearson Education, Inc.

Chapter 4

4.5 Isomerism in Organic Compounds, Part 1,


Continued

Each compound contains four carbon atoms and


10 hydrogen atoms. Each have the molecular
formula, C4H10.
The four carbons in the compound on the right
are not connected in a continuous chain as they
are in butane.

2011 Pearson Education, Inc.

Chapter 4

4.5 Isomerism in Organic Compounds, Part 1,


Continued
The second structural isomer of butane forms a
branched alkane and is known as isobutane.
Branched-chain alkanes do not have all their
carbon atoms connected in a single continuous
chain.
Both compounds with the molecular formula of
C4H10 are structural isomers. That is, they have
different connectivity of the atoms.
2011 Pearson Education, Inc.

Chapter 4

4.5 Isomerism in Organic Compounds, Part 1,


Continued
Conformational Isomers
Conformational isomers are isomers that are
not different compounds because they have
different arrangements of the atoms of the
compound. They are also known as
conformers.
Consider butane. The structure of butane can be
represented as shown on the next slide.
2011 Pearson Education, Inc.

Chapter 4

4.5 Isomerism in Organic Compounds, Part 1,


Continued

These two representations are conformational


isomers of the same molecule.
These molecules are not rigid. Since there is
rotation about the single bonds of butane, the
molecule can form the two conformational
isomers.
2011 Pearson Education, Inc.

Chapter 4

4.5 Isomerism in Organic Compounds, Part 1,


Continued
The three-dimensional models of the two
conformational isomers of butane that demonstrate
the rotation about the carboncarbon single bond
is shown as:

2011 Pearson Education, Inc.

Chapter 4

4.5 Isomerism in Organic Compounds, Part 1,


Continued
Nomenclature of Simple Organic Compounds
Systematically naming each organic compound
is a useful method to determine whether two
compounds are structural or conformational
isomers.
Structural isomers will have different names,
whereas conformational isomers will have the
same name.
Naming of organic compounds was developed
by the International Union of Pure and Applied
Chemistry, or IUPAC.
2011 Pearson Education, Inc.

Chapter 4

4.5 Isomerism in Organic Compounds, Part 1,


Continued
Branched-Chain Alkanes

Consider the following branched-chain


isomer of butane, isobutane. Naming will be
done using the IUPAC system.

2011 Pearson Education, Inc.

Chapter 4

4.5 Isomerism in Organic Compounds, Part 1,


Continued
Branched-Chain Alkanes, Continued

The following are rules for naming branchedchain alkanes by the IUPAC system:
Step 1. Find the longest continuous chain of
carbon atoms. This is the parent chain. Name
the parent according to the alkane name for
the appropriate number of carbon atoms. In
this case, the parent chain is propane.

2011 Pearson Education, Inc.

Chapter 4

4.5 Isomerism in Organic Compounds, Part 1,


Continued
Branched-Chain Alkanes, Continued
Step 2. Identify the groups bonded to the
parent chain and not included in the main
chain. These groups are called substituents
and in this case, called alkyl groups. The
name of the alkyl group is derived from the
alkane with the same number of carbon atoms
by changing the -ane ending with -yl. For
example, a one carbon alkyl group is named
as a methyl group.

2011 Pearson Education, Inc.

Chapter 4

10

4.5 Isomerism in Organic Compounds, Part 1,


Continued
Branched-Chain Alkanes, Continued
Step 2 (continued). This table shows the
simplest alkyl substituents and their point of
attachment to the parent chain.

2011 Pearson Education, Inc.

Chapter 4

11

4.5 Isomerism in Organic Compounds, Part 1,


Continued
Branched-Chain Alkanes, Continued
Step 2 (continued). In our case, the
substituent is the methyl group.

2011 Pearson Education, Inc.

Chapter 4

12

4.5 Isomerism in Organic Compounds, Part 1,


Continued
Branched-Chain Alkanes, Continued
Step 3. Number the parent chain starting at
the end nearer to a substituent. In our
example, the substituent is on carbon 2 no
matter which end you start numbering.

2011 Pearson Education, Inc.

Chapter 4

13

4.5 Isomerism in Organic Compounds, Part 1,


Continued
Branched-Chain Alkanes, Continued
Step 4. Assign a number to each
substituent based on location, listing the
substituents in alphabetical order at the
beginning of the name. Separate numbers
and words in the name by a dash. Separate
numbers by a comma. The IUPAC name for
our example is 2-methylpropane.

2011 Pearson Education, Inc.

Chapter 4

14

4.5 Isomerism in Organic Compounds, Part 1,


Continued
Branched-Chain Alkanes, Continued
NOTE: If more than one substituent of the same
type is present, indicate this by using the prefixes
di-, tri-, and tetra-, but ignore these prefixes when
alphabetizing. For example, two methyl groups on a
parent chain would be named dimethyl.

2011 Pearson Education, Inc.

Chapter 4

15

4.5 Isomerism in Organic Compounds, Part 1,


Continued
Haloalkanes
Halogens can serve as substituents on alkane
chains and are known as haloalkanes, or
alkyl halides.
When a halogen is present, the name of the
halogen is changed by replacing the -ine
ending with an -o.
Names of halogen substituents become fluoro,
chloro, bromo, and iodo.
Rules for naming haloalkanes are the same
for naming branched-chain alkanes.
2011 Pearson Education, Inc.

Chapter 4

16

4.5 Isomerism in Organic Compounds, Part 1,


Continued
Cycloalkanes

Rules for naming cylcoalkanes are as


follows:
Step 1. The ring serves as the parent.
Step 2. As in branched-chain alkanes,
identify the substituents.
Step 3. Number the carbons giving the
carbon with the substituent as carbon 1.

2011 Pearson Education, Inc.

Chapter 4

17

4.5 Isomerism in Organic Compounds, Part 1,


Continued
Cycloalkanes, Continued
Step 4. Assign numbers to the
substituents. If only one substituent is
present, it is assumed to be in position 1
and the 1 is implied and not listed. When
more than one substituent is present, give
all substituents the lowest possible
numbers.

2011 Pearson Education, Inc.

Chapter 4

18

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