ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY
ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY
4th Edition
ISBN: 9781119761105
Author: Klein
Publisher: WILEY
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Chapter 18.15, Problem 36PTS
Interpretation Introduction

Interpretation:

The structures of the product obtained have to be drawn when 2-ethyl-5-chlorotoluene is treated with Sodium hydroxide at high temperature followed by treatment with H3O+.

Concept Introduction:

  • Aromatic compounds undergo another type of reactions namely Aromatic nucleophilic substitution reactions designated as SNAr .
  • A nucleophile, unlike an electrophile is a species that is electron rich and always attracted towards electron deficient site. A nucleophile is mobile unlike electrophile.
  • The criteria for aromatic nucleophilic substitution reaction to occur are –
  • The aromatic ring must contain a strong electron withdrawing group
  • The aromatic ring must contain a leaving group
  • The leaving group must be posited either ortho or para position to the strong electron withdrawing group.
  • In case where there is no possibility of SNAr reactions the compounds undergo another type of reaction under different reaction conditions called elimination – addition reaction. A compound with leaving group when treated with a strong base under high or low temperature undergoes elimination – addition reaction where the leaving group is eliminated and a new group is added.
  • The term Regioselectivity is referred as preference of a particular group to occupy a specific position in a compound. In case an aromatic ring has one or more than one substituents the position in the aromatic ring occupied by the incoming electrophile depends on various factors.

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For this question, if the product is racemic, input both enantiomers in the same Marvin editor. A) Input the number that corresponds to the reagent which when added to (E)-but-2-ene will result in a racemic product. Input 1 for Cl, in the cold and dark Input 2 for Oy followed by H₂O, Zn Input 3 for D₂ with metal catalyst Input 4 for H₂ with metal catalyst B) Draw the skeletal structure of the major organic product made from the reagent in part A Marvin JS Help Edit drawing C) Draw the skeletal structure of the major organic product formed when (2)-but-2-ene is treated with peroxyacetic acid. Marvin 35 Help
Michael Reactions 19.52 Draw the products from the following Michael addition reactions. 1. H&C CH (a) i 2. H₂O* (b) OEt (c) EtO H₂NEt (d) ΕΙΟ + 1. NaOEt 2. H₂O' H H 1. NaOEt 2. H₂O*
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