Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 7.SE, Problem 29MP
When methyl vinyl ether reacts with a strong acid, the proton adds to C2 exclusively, instead of C1 or the oxygen atom. Draw the three protonated forms of methyl vinyl ether and explain this observation.
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- A benzene ring alters the reactivity of a neighboring group in the so-called “benzylic” position, similarly to how a double bond alters the reactivity of groups in the “allylic” position. Benzylic cations, anions, and radicals are all more stable than simple alkyl intermediates. a) Use resonance structures to show the delocalization of the positive charge, negative charge, and unpaired electron of the benzyl cation, anion, and radical.arrow_forwardAnswer only f, g and h part .arrow_forwardThe bond dissociation energy of one of the C–H bonds is considerablyless than the bond dissociation energy of the other. Which C–H bondis weaker? Offer an explanation.arrow_forward
- Explain why triphenylene resembles benzene in that it does not undergo addition reactions with Br2, but phenanthrene reacts with Br2 to yield the addition product drawn. (Hint: Draw resonance structures for both triphenylene and phenanthrene, and use them to determine how delocalized each π bond is.)arrow_forwardFor each pair of compounds, predict which one has the higher molecular dipole moment, and explain your reasoning.(a) cis-2,3-dibromobut-2-ene or trans-2,3-dibromobut-2-enearrow_forwardBelow is the structure for beta-carotene, a pigment found in plants and vegetables that give them their color. Determine how many alkenes are properly trans in the structure.arrow_forward
- comparing to this two ketone, which ketone has the most stable π system? Explain on the basis of the carbonyl group.arrow_forwardDefine the consequence of resonance stabilization ?arrow_forwardProvide the bond line structure of a compound that is able to undergo Allylic lone pair and allylic carbocation resonance. Provide all resonance structures and appropriate arrows. Indicate which resonance state is most stable and why.arrow_forward
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