ORGANIC CHEM. - ACCESS PKG+MODELING KIT
ORGANIC CHEM. - ACCESS PKG+MODELING KIT
4th Edition
ISBN: 9781119838746
Author: Klein
Publisher: WILEY
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Chapter 18.13, Problem 31CC
Interpretation Introduction

Interpretation:

The synthesis of the following compound has to be illustrated using benzene as the starting compound.

                                                  ORGANIC CHEM. - ACCESS PKG+MODELING KIT, Chapter 18.13, Problem 31CC

Concept Introduction:

  • Electrophilic substitution reactions of aromatic compounds are known as aromatic electrophilic substitution reactions. An electrophile is a species that is deficient of electrons.
  • Benzene is an electron rich Aromatic compound. It undergoes aromatic electrophilic substitution reaction.  The delocalized nature of pi electrons in benzene attributes a special property to benzene called resonance.
  • The various types of electrophilic substitution reactions in benzene are – Chlorination, Bromination, Nitration, Sulfonation, Friedel Crafts Alkylation/Acylation etc.
  • Apart from electrophilic substitution reactions benzene and its derivatives also undergo another special type of reactions namely Aromatic nucleophilic substitution reactions.
  • 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.

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1,4-Dimethyl-1,3-cyclohexadiene can undergo 1,2- or 1,4-addition with hydrogen halides. (a) 1,2-Addition i. Draw the carbocation intermediate(s) formed during the 1,2-addition of hydrobromic acid to 1,4-dimethyl-1,3-cyclohexadiene. ii. What is the major 1,2-addition product formed during the reaction in (i)? (b) 1,4-Addition i. Draw the carbocation intermediate(s) formed during the 1,4-addition of hydrobromic acid to 1,4-dimethyl-1,3-cyclohexadiene. ii. What is the major 1,4-addition product formed from the reaction in (i)? (c) What is the kinetic product from the reaction of one mole of hydrobromic acid with 1,4-dimethyl-1,3-cyclohexadiene? Explain your reasoning. (d) What is the thermodynamic product from the reaction of one mole of hydrobro-mic acid with 1,4-dimethyl-1,3-cyclohexadiene? Explain your reasoning. (e) What major product will result when 1,4-dimethyl-1,3-cyclohexadiene is treated with one mole of hydrobromic acid at - 78 deg * C ? Explain your reasoning.
Give the product of the bimolecular elimination from each of the isomeric halogenated compounds. Reaction A Reaction B. КОВ CH₂ HotBu +B+ ко HOIBU +Br+ Templates More QQQ Select Cv Templates More Cras QQQ One of these compounds undergoes elimination 50x faster than the other. Which one and why? Reaction A because the conformation needed for elimination places the phenyl groups and to each other Reaction A because the conformation needed for elimination places the phenyl groups gauche to each other. ◇ Reaction B because the conformation needed for elimination places the phenyl groups gach to each other. Reaction B because the conformation needed for elimination places the phenyl groups anti to each other.
Five isomeric alkenes. A through each undergo catalytic hydrogenation to give 2-methylpentane The IR spectra of these five alkenes have the key absorptions (in cm Compound Compound A –912. (§), 994 (5), 1643 (%), 3077 (1) Compound B 833 (3), 1667 (W), 3050 (weak shoulder on C-Habsorption) Compound C Compound D) –714 (5), 1665 (w), 3010 (m) 885 (3), 1650 (m), 3086 (m) 967 (5), no aharption 1600 to 1700, 3040 (m) Compound K Match each compound to the data presented. Compound A Compound B Compound C Compound D Compound

Chapter 18 Solutions

ORGANIC CHEM. - ACCESS PKG+MODELING KIT

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