Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 11.9, Problem 19P
Interpretation Introduction
Interpretation:
In which isomer the E2 elimination occurs faster is interpreted. The more stable chair confirmation is drawn to explain the reaction.
Concept introduction:
If the leaving group and hydrogen are trans diaxial only the E2 elimination occurs in cyclohexane rings. The E2 elimination occurs by Zaitsevs rule.
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Chapter 11 Solutions
Organic Chemistry
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- Draw the starting alkene that would lead to this the major product (and its enantiomer) under these conditions. Drawing H2 Pd/C OD0 000 F5 F4arrow_forwardDraw the Newman projection (sighting down this bond) of the conformation that will be capable of an E2 elimination. R/S stereochemistry is graaded. CH3 H. H. CH3 Please selec Br Harrow_forward11. Trans-1-bromo-2-methylcyclohexane will yield a non-Zaitsev elimination product (3- methylcyclohexene) upon reaction with KOH. Show this reaction by drawing the chair conformations of the reactant and product. Include the curved arrows and explain why the product is not a non-Zaitsev product. (arrow_forward
- Ketones react with alcohols to yield products called acetals. Why does the all-cis isomer of 4-tert-butyl-1,3-cyclohexanediol react readily with acetone and an acid catalyst to form an acetal, but other stereoisomers do not react? In formulating your answer, draw the more stable chair conformations of all four stereoisomers and the product acetal for each one.arrow_forward(a) When cis-1-bromo-2-methylcyclohexane undergoes an E2 reaction, two products (cycloalkenes) are formed. What are these two cycloalkenes, and which would you expect to be the major product? Write conformational structures showing how each is formed. (b) When rans-1-bromo-2-methylcyclohexane reacts in an E2 reaction, only one cyclo- alkene is formed. What is this product? Write conformational structures showing why it is the only product.arrow_forwardDraw each of the above molecules in a 3D perspective. Show all six-membered rings as chairs and all acyclic torsions in staggered conformation. If multiple conformations are possible, choose the best one.arrow_forward
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