1. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.1 Chapter 11 Introduction to Organic Chemistry: Alkanes 11.3 Alkanes with Substituents

2. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. Isomers of Butane Isomers  have the same molecular formula  have different structural arrangements  of butane (C 4 H 10 ) consist of a straight chain and a branched chain each with 4 carbon atoms Branch or substituent 2

3. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.3 Substituents Substituents are  attached to carbon chains  carbon branches that are missing one H and named as alkyl groups  halogen atoms that are named as halo substituents

4. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.4 Alkanes with Alkyl Groups 2,4-dimethylpentane methylpropane

5. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.5 Naming Alkanes with Substituents

6. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. Give the name of STEP 1 Write the name of the longest chain: butane STEP 2 Number the chain from the end nearer a branch: STEP 3 Give location and names of substituents: 2-Methylbutane 6 Example of Naming Alkanes

7. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.7 Learning Check Write the IUPAC name for:

8. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.8 Solution STEP 1 Write the name of the longest chain: pentane STEP 2 Number chain from end nearer substituents: STEP 3 Give location and name substituents alphabetically: 3-Chloro-2-methylpentane

9. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.9 Learning Check Give the IUPAC name for each of the following:

10. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.10 Solution 1 2,4-dimethylhexane 23456 more substituents on C3 7 3,5-dichloro-3-methylheptane 654321

11. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.11 Guide to Drawing Alkane Structures

12. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.12 What Is in a Name? The structural formula is drawn from the IUPAC name. 2,4-dimethylhexane 2,4 dimethyl hexane Location of Two CH 3 -groups 6-carbon main chain branches on attached with single C—C bonds main chain

13. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.13 Learning Check Draw the condensed structural formula for 3-bromo-1-chlorobutane.

14. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.14 Solution STEP 1 Draw a chain with 4 carbon atoms: C─C─C─C STEP 2 Number the chain and add substituents: STEP 3 Add hydrogen (H) to give four bonds to each C:

15. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.15 Naming Cycloalkanes with Substituents The name of a substituent is placed in front of the cycloalkane name. Methylcyclobutane When there are two substituents, number the ring 1-bromo-2-chlorocyclopentane

16. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.16 Learning Check Name each of the following:

17. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.17 Solution Name each of the following: methylcyclopropane 3-Chloro-1-ethylcyclohexane

18. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.18 Write three isomers of C 5 H 12, and name each. Learning Check

19. General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.19 A chain of 5 carbon atoms: CH 3 ─CH 2 ─CH 2 ─CH 2 ─CH 3 pentane A chain of 4 carbon atoms and 1 carbon branch: 2-methylbutane A chain of 3 carbon atoms and 2 carbon branches: 2,2-dimethylpropane Solution