1. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Chapter 10 Introduction to Organic Chemistry: Alkanes 10.3 Alkanes with Substituents 1

2. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Isomers of Butane Isomers have the same molecular formula with different atom arrangements of butane (C 4 H 10 ) are a straight chain and a branched chain The isomers of butane have the same number and type of atoms, but the atoms are bonded in a different order. 2

3. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Substituents and Alkyl Groups Substituents are atoms or groups of atoms attached to the carbon chain and include alkyl and halo groups. Alkyl groups are carbon branches attached to carbon chains named with a yl ending Halo substituents are halogens attached to the carbon chain named as fluoro, chloro, bromo, or iodo 3

4. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Substituents and Alkyl Groups 4

5. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Guide to Naming Alkanes with Substituents 5

6. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Write IUPAC Names for Alkanes with Substituents Give the IUPAC name for the following compound: Step 1 Write the alkane name of the longest chain of carbon atoms. The longest chain has five carbons, pentane. 6

7. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Write IUPAC Names for Alkanes with Substituents Step 2 Number the carbon atoms starting from the end nearer a substituent. Step 3 Give the location and name of each substituent (in alphabetical order) as a prefix to the name of the main chain. 2-chloro-3-methylpentane 7

8. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Give the IUPAC name for the following compound: 8

9. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Give the IUPAC name for the following compound: Step 1 Write the alkane name of the longest chain of carbon atoms. The longest chain has four carbons, butane. 9

10. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Step 2 Number the carbon atoms starting from the end nearer a substituent. Step 3 Give the location and name of each substituent (in alphabetical order) as a prefix to the name of the main chain. 1,2-dibromo-3-methylbutane 10

11. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Cycloalkanes with Substituents Give the IUPAC name for the following cycloalkane. Step 1 Write the alkane name of the longest chain of carbon atoms. The longest chain is a six-member ring, cyclohexane. 11

12. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Step 2 Number the carbon atoms starting from the end nearer a substituent. Step 3 Give the location and name of each substituent (in alphabetical order) as a prefix to the name of the main chain. For cycloalkanes with just one substituent, there is no need to give the location of the substituent: ethylcyclohexane 12

13. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Drawing Formulas for Alkanes 13 Draw the structure for 1-chloro-1,2-dimethylheptane heptane – 7-carbon chain methyl group on carbon 1 and 2 chlorine on carbon 1

14. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Guide to Drawing Formulas for Alkanes 14

15. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Draw the condensed structural formula for 3-bromo-1-chlorobutane. 15

16. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Draw the condensed structural formula for 3-bromo-1-chlorobutane. Step 1Draw the main chain of carbon atoms. The longest chain in butane has four carbon atoms.C  C  C  C Step 2Number chain and place the substituents on the carbons indicated by the numbers. 1 2 3 4 3-bromo:  Br goes on carbon 3. C  C  C  C Cl Br 1-chloro:  Cl goes on carbon 1. 16

17. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Draw the condensed structural formula for 3-bromo-1-chlorobutane. Step 3 Add hydrogen to complete four bonds to each carbon. CH 2  CH 2  CH  CH 3   Cl Br 3-bromo-1-chlorobutane 17

18. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Learning Check Name each of the following cycloalkanes. A. B. C. 18

19. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Solution Name each of the following cycloalkanes. A. methylcyclopropane B. ethylcyclobutane C. chlorocyclopentane 19