Wade06a - Chapter 6 Alkyl Halides Nucleophilic Substitution...

Info iconThis preview shows pages 1–11. Sign up to view the full content.

View Full Document Right Arrow Icon

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Chapter 6 Alkyl Halides: Nucleophilic Substitution and Elimination Organic Chemistry , 5 th Edition L. G. Wade, Jr. Chapter 6 2 Classes of Halides • Alkyl: Halogen, X, is directly bonded to sp 3 carbon. • Vinyl: X is bonded to sp 2 carbon of alkene. • Aryl: X is bonded to sp 2 carbon on benzene ring. Examples: C H H H C H H Br alkyl halide C C H H H Cl vinyl halide I aryl halide => Chapter 6 3 Polarity and Reactivity • Halogens are more electronegative than C. • Carbon-halogen bond is polar, so carbon has partial positive charge. • Carbon can be attacked by a nucleophile. • Halogen can leave with the electron pair. => C H H H Br δ + δ- Chapter 6 4 Classes of Alkyl Halides • Methyl halides: only one C, CH 3 X • Primary: C to which X is bonded has only one C-C bond. • Secondary: C to which X is bonded has two C-C bonds. • Tertiary: C to which X is bonded has three C-C bonds. => Chapter 6 5 Classify These: CH 3 CH CH 3 Cl CH 3 CH 2 F (CH 3 ) 3 CBr CH 3 I => Chapter 6 6 Dihalides • Geminal dihalide: two halogen atoms are bonded to the same carbon • Vicinal dihalide: two halogen atoms are bonded to adjacent carbons. C H H H C H Br Br geminal dihalide C H H Br C H H Br vicinal dihalide => Chapter 6 7 IUPAC Nomenclature • Name as haloalkane. • Choose the longest carbon chain, even if the halogen is not bonded to any of those C’s. • Use lowest possible numbers for position. CH 3 CH CH 2 CH 3 Cl CH 3 (CH 2 ) 2 CH(CH 2 ) 2 CH 3 CH 2 CH 2 Br 2-chlorobutane 4-(2-bromoethyl)heptane => Chapter 6 8 Systematic Common Names • Name as alkyl halide. • Useful only for small alkyl groups. • Name these: CH 3 CH CH 2 CH 3 Cl (CH 3 ) 3 CBr CH 3 CH CH 3 CH 2 F => Sec-butyl chloride T-butyl Bromide iso-butyl fluoride Chapter 6 9 “Trivial” Names • CH 2 X 2 called methylene halide. • CHX 3 is a haloform. • CX 4 is carbon tetrahalide. • Examples: CH 2 Cl 2 is methylene chloride CHCl 3 is chloroform CCl 4 is carbon tetrachloride. => Chapter 6 10 Uses of Alkyl Halides • Solvents - degreasers and dry cleaning fluid • Reagents for synthesis of other compounds • Anesthetic: Halothane (trade name) is CF 3 CHClBr CHCl 3 used originally (toxic and carcinogenic) • Freons, chlorofluorocarbons or CFC’s Freon 12, CF 2 Cl 2 , now replaced with Freon 22, CHClF 2 , not as harmful to ozone layer. • Pesticides - DDT banned in U.S....
View Full Document

{[ snackBarMessage ]}

Page1 / 55

Wade06a - Chapter 6 Alkyl Halides Nucleophilic Substitution...

This preview shows document pages 1 - 11. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online