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Unformatted text preview: Organic Reactions 1 Copyright, Arizona State University Copyright, Arizona State University Organic Reactions How and Why Reactions "Go" 1 Different Kinds of Reactions We NEED some language to distinguish among various kinds of organic reactions 1. Addition Reactions (introduced in Alkenes) A + B A–B H–Br + C H 3 C H C H H 3 C C H 3 C H C H H 3 C Br H • H and Br are added to the C=C double bond of the alkene 2. Substitution Reactions (introduced in Alkyl Halides) A + X–Y A–X + Y HO + H 3 C–Br HO–CH 3 + Br • OH is substituted for Br in the alkyl halide 3. Elimination Reactions (introduced in Alkyl Halides) X + Y X–Y C H CH 3 C Br H CH 3 H +) C H 3 C H C H H 3 C (HO–H +) + Br (HO • H and Br are eliminated from the alkyl bromide • the HO – is required to "make" this particular elimination reaction "go" 4. Rearrangement Reactions (introduced later in Alkynes, Alcohols etc.) A B H 3 C C OH CH 2 H 3 C C O CH 3 (H 3 O + ) • the reactant and product are structural isomers, the bonds are rearranged, nothing is added or removed • the H 3 O + is required to "help" this particular rearrangement reaction "go", it is a catalyst 5. Protonation/Deprotonation Reactions (seen previously) H–A + B A + H–B Me Me C O H Cl + Me Me C O Cl + H • A proton is transferred from the acid (H-Cl) to the ketone • the ketone becomes protonated • the H-Cl becomes deprotonated Organic Reactions 2 Copyright, Arizona State University Copyright, Arizona State University Organic Reactions PROBLEMS Classification of Reactions In each case, indicate whether the reaction is an addition, elimination, substitution or rearrangement (we will meet all of these reactions later in the course) 1 (standard) + PPh 3 OTs PPh 3 + OTs Answer Correct Y / N 2 (standard) CO 2 Me CO 2 Me CO 2 Me CO 2 Me + Δ (= heat) Answer Correct Y / N 3 (standard) H H H H H H NO 2 H H H H H HNO 3 /H 2 SO 4 Answer Correct Y / N 4 (standard) Δ (= heat) Answer Correct Y / N 5 (standard) conc. H 2 SO 4 /heat OH + H 2 O Answer Correct Y / N 6 (standard) Pd + H 2 Answer Correct Y / N 7 (standard) Δ (= heat) Answer Correct Y / N 8 (standard) – OMe/MeOH Br + HOMe + Br – Answer Correct Y / N Answers provided on the website.... Doing problems is the only way that you will learn organic chemistry. You should do problems in the notes, from the textbook and from problem sets. It is CRITICAL that you keep track of what you know and what you don't know. Each notes problem has a "Correct Y / N" box. When you are PROPERLY CONVINCED that you can do a problem, circle "Y", if you can't do the problem circle "N". Keep coming back to those problems with the circled "N", until you can circle the "Y"....
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This note was uploaded on 01/07/2012 for the course CHM 233 taught by Professor Skibo during the Fall '08 term at ASU.
- Fall '08