Lecture25-notes

Lecture25-notes - 1 Chapter 9 Reading 9.1-9.9 Practice...

Info iconThis preview shows pages 1–6. 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 DocumentRight Arrow Icon

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

View Full DocumentRight Arrow Icon

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

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

Unformatted text preview: 10/26/09 1 Chapter 9 Reading: 9.1-9.9 Practice problems: those in assigned text and 29-35, 37-40 Substitution and Elimination Reactions of Alkyl Halides SUBSTITUTION REACTIONS Y + R X R Y + X Y takes the place of X (Substitution) Y “displaces” X One group takes the place of another. 10/26/09 2 N u :- + R X R N u + :X- nucleophile substrate product leaving group NUCLEOPHILIC DISPLACEMENT The nucleophile “displaces” the leaving group. This is a “substitution” reaction: Nu substitutes for X (takes its place). NUCLEOPHILIC SUBSTITUTION Example 1 iodide displaces bromide at carbon NaI is soluble in acetone, NaCl and NaBr are not * 10/26/09 3 Example 2 solvolysis of isopropyl chloride in water The extra proton is taken by a second water molecule. * water displaces chloride at carbon NUCLEOPHILIC SUBSTITUTION REACTIONS (substitution at carbon) ACID – BASE REACTIONS (substitution at hydrogen) can be compared to … DISPLACEMENT REACTIONS 10/26/09 4 COMPARE THESE REACTIONS N u :- + R X R N u + :X- nucleophile substrate product leaving group DISPLACEMENT AT CARBON base acid conjugate acid conjugate base :X- + B H H X + B :- DISPLACEMENT AT HYDROGEN 10/26/09 5 R O R' R ' C C R R ' C O O R NUCLEOPHILES A WIDE SELECTION OF NUCLEOPHILES MAKES POSSIBLE THE SYNTHESIS OF MANY TYPES OF ORGANIC COMPOUNDS: Nucleophile Product R X alkyl halides R O H alcohols ethers C N R nitriles esters alkynes R S H thiols Class R-Y + Nu R-Nu + Y R ' O- R ' N H R O R' R THE NUCLEOPHILE DOES NOT NEED TO BE CHARGED HOWEVER, REACTIVE ATOMS BEAR A LONE PAIR Nucleophile Product alcohols Class O H H O R H ethers O R H R N H 2 amines R ' N H 2 N H 3 amines O H H + R B r O H H R + + B r O H R O H H + H 3 O + + B r - - Under some circumstances water will react....
View Full Document

This note was uploaded on 07/02/2011 for the course CHEM R340 taught by Professor Tolbert during the Summer '11 term at Indiana.

Page1 / 23

Lecture25-notes - 1 Chapter 9 Reading 9.1-9.9 Practice...

This preview shows document pages 1 - 6. Sign up to view the full document.

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