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B. Substituted Alkanes

B. Substituted Alkanes. In many hydrocarbons, some of the “H”s are replaced with other groups. These groups can be single atoms or groups of atoms. 1. Halogenated Alkanes. These are normal alkanes with group 17 (halogens) on them. H Br | | H - C - C - H

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B. Substituted Alkanes

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  1. B. Substituted Alkanes In many hydrocarbons, some of the “H”s are replaced with other groups These groups can be single atoms or groups of atoms 1. Halogenated Alkanes These are normal alkanes with group 17 (halogens) on them H Br | | H - C - C - H | | H H This is a normal alkane with a bromine atom on it Rules for naming substituted alkanes a. The longest chain of carbon atoms is the base name Last part of the name

  2. Cl H | | H - C - C - H H H H | | | | | H H-C - C - C - C - H | | | | H HH H This has six carbons in the longest chain, so it is some form of Hexane 1 2 b. The carbons are numbered to indicate each carbon atom 3 5 4 6 1- Chloro Hexane c. Write the halogen group name before the base name Cl Br F I Chloro Bromo Fluoro Iodo d. Name the location of the extra group Since the chlorine is on the first carbon, it is 1-chloro Where the group is attached 3-bromo octane Name of longest chain Name of group attached to chain

  3. Important point Name these compounds H H | | H - C - C - Br | | H H H H | | Br- C - C - H | | H H H H | | H - C - C - Br | | H H H H | | H - C - C - Br | | H H H H | | H - C - C - Br | | H H H H | | H - C - C - Br | | H H H H | | H - C - C - Br | | H H H H | | Br- C - C - H | | H H 2-bromo ethane 1-bromo ethane They are actually the same, one is just flipped over. To avoid this The hydrocarbon chain is numbered so that the extra groups have the lowest number possible H H | | H - C - C - H H H H | | | | | H H-C - C - C - C - H | | | | H H Cl H This is 2-chloro hexane, not 5-chloro hexane 5 6 1 2 4 3 Start numbering the chain on the side closest to the extra group

  4. Examples - Name the following I H | | H - C - C - H | | H H H H | | H - C - C - H H H | | | | H H-C - C - C - H | | | Br HH H Cl H H | | | | H-C - C - C - C - H | | | | H HHH a. b. c. 1- iodo ethane 2- chloro butane 3- bromo pentane

  5. d. If a group appears more than once, we number both places and add di tri tetra to the halogen prefix 2 3 4 H H | | H - C - C - H Cl H H | | | | | H H-C - C - C - C - H | | | | H H Cl H This hexane has a chlorine on carbons #2 and #3 Called 2,3 - dichloro hexane Examples - Name the following Cl Cl H H | | | | H-C - C - C - C - H | | | | H HHH a. b. I H | | H - C - C - H | | H I c. H H | | H - C - C- H Br H | | | | H H-C - C - C - H | | | BrBr H 1,2- dichloro butane 1,2- diiodo ethane 2,2,3- tribromo pentane

  6. e. When different halogens are added, alphabetize the prefix names Cl Br | | H - C - C - H H H H | | | | | H H-C - C - C - C - H | | | | H HHH This has a Chlorine on #1 and a Bromine on #2, so bromine comes first 2-bromo, 1-chloro hexane Examples - Name the following Cl F H H | | | | H-C - C - C - C - H | | | | H HHH a. b. I H | | H - C - C - H | | ClI c. H H | | I - C - C- H Br H | | | | Cl H-C - C - C - H | | | BrBr H 1 chloro 2-fluoro butane 1-chloro 1,2-diiodo ethane 3,4,4-tribromo 1-chloro 1-iodo pentane

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