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Chapter 11 Introduction to Organic Chemistry: Alkanes

Chapter 11 Introduction to Organic Chemistry: Alkanes. 11.3 Alkanes with Substituents. 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.

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Chapter 11 Introduction to Organic Chemistry: Alkanes

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  1. Chapter 11 Introduction to Organic Chemistry: Alkanes 11.3 Alkanes with Substituents

  2. Isomers of Butane Isomers • have the same molecular formula • have different structural arrangements • of butane (C4H10) consist of a straight chain and a branched chain each with 4 carbon atoms Branch or substituent 2

  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. Alkanes with Alkyl Groups methylpropane 2,4-dimethylpentane

  5. Naming Alkanes with Substituents

  6. Example of Naming Alkanes 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 3Give location and names of substituents: 2-Methylbutane

  7. Learning Check Write the IUPAC name for:

  8. Solution STEP 1 Write the name of the longest chain: pentane STEP 2Number chain from end nearer substituents: STEP 3Give location and name substituents alphabetically: 3-Chloro-2-methylpentane

  9. Learning Check Give the IUPAC name for each of the following:

  10. Solution 2,4-dimethylhexane 1 2 3 4 5 6 more substituents on C3 7 6 5 4 3 2 1 3,5-dichloro-3-methylheptane

  11. Guide to Drawing Alkane Structures

  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 CH3-groups 6-carbon main chain branches on attached with single C—C bonds main chain

  13. Learning Check Draw the condensed structural formula for 3-bromo-1-chlorobutane.

  14. Solution STEP 1Draw a chain with 4 carbon atoms: C─C─C─C STEP 2Number the chain and add substituents: STEP 3Add hydrogen (H) to give four bonds to each C:

  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. Learning Check Name each of the following:

  17. Solution Name each of the following: methylcyclopropane 3-Chloro-1-ethylcyclohexane

  18. Learning Check Write three isomers of C5H12, and name each.

  19. Solution A chain of 5 carbon atoms: CH3─CH2─CH2─CH2─CH3 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

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