Consider the addition of HBr shown here. (a) Draw all four carbocation intermediates possible from protonation of the diene and identify the most stable one. + HBr (b) Draw both halogenated products formed by attack of Br on that carbocation. (c) Which of those products would you expect to be formed in the greatest amount at low temperatures? (d) Which would you expect to be formed in the greatest amount at high temperatures?

Consider the addition of HBr shown here. (a) Draw all four carbocation intermediates possible from protonation of the diene and identify the most stable one. + HBr (b) Draw both halogenated products formed by attack of Br on that carbocation. (c) Which of those products would you expect to be formed in the greatest amount at low temperatures? (d) Which would you expect to be formed in the greatest amount at high temperatures?

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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A student adds NBS to a solution of 1-methylcyclohexene and irradiates the mixture with a sunlamp until all the NBS has reacted. After a careful distillation, the product mixture contains two major products of formula C7H11Br. (a) Draw the resonance forms of the three possible allylic free radical intermediates.
Consider the addition of HBr shown here. HBr (a) Draw all four carbocation intermediates possible from protonation of the diene. (b) Identify the most stable carbocation. (b) Draw both halogenated products formed by attack of Br, on the most stable carbocation. (c) Which of those products would you expect to be formed in the greatest amount at low temperatures? (d) Which would you expect to be formed in the greatest amount at high temperatures?
Consider the addition of HBr shown here. HBr (a) There are three carbocation intermediates possible from the protonation of this triene. Draw all three of them and identify the most stable one. (b) Draw all halogenated products formed by attack of Br on the most stable carbocation. (c) Which of those products would you expect to be formed in the greatest amount at low temperatures? (d) Which would you expect to be formed in the greatest amount at high temperatures?
When treated with NaOH, the bromide below gives an alkene by the E2 mechanism, by elimination of the H atom indicated by the arrow: (a) Draw the Newman projection from which elimination takes place. (b) Draw the mechanism. (c) Draw the product with the proper stereochemistry. (d) Assign the proper stereochemical descriptor to the product. (e) Give the rate equation
According to the rules for reasonable mechanisms, the E1 reaction shown here should undergo a 1,2-hydride shift. However, the same product is produced regardless of whether the rearrangement occurs. Br H20, heat (a) Draw the mechanism that includes that carbocation rearrangement. (b) Draw the mechanism that does not include the rearrangement. (c) Experimentally, how can we use 13C isotope labeling to determine whether the rearrangement occurs? In other words, can a 1ºc atom in the substrate be replaced by a 1°C atom so that the E1 products would depend on whether the rearrangement takes place? (d) How can we use deuterium isotope labeling to determine whether the rearrangement occurs?
The alkene shown undergoes bromination. (a) Draw the product(s) of bromination of this compound, including all expected stereoisomers (if any). Use wedge‑and‑dash bonds to designate the stereochemistry at any chirality centers, and make sure to draw an explicit hydrogen if a chirality center has one. (b) Characterize the starting alkene as having the E or Z configuration. (c) characterize the product(s).
4) Draw the complete electron-pushing arrow mechanism for the following reductions. Explain, using resonance contributors, the regiochemistry that results in each case. ỌMe Na, MeOH ? NH3 CHO Na, MeOH ? NH3
(b) Consider the reaction of 1-bromobutane with a large excess of ammonia (NH3). Draw the reactants, the transition state, andthe products. Note that the initial product is the salt of an amine (RNH3+ Br - ), which is deprotonated by the excess ammonia to give the amine.
10) Consider the following alkene hydration reaction. он H2SO, H20 Given that the reaction is endergonic by 10 kcal/mol, complete the following. (a) Draw the intermediate(s) formed in the mechanistic pathway to the major product in the indicated space below. If there are multiple intermediates label them 1, 2, 3, 4, etc. (b) Sketch a reaction-energy profile for this reaction and clearly label staring material, product, intermediate(s), transition state(s), AG" and AG (of the rate determining step) on your plot. Progress of the reaction Draw and Label Intermediate(s) Below: Potential energy
(a) Name the reactant (including E/Z configuration) and draw the structure of the major product for the following reaction. + HBr (b) Explain your answer for the product in part (a), and include the structure of the carbocation intermediate in your explanation. (c) Draw the mechanism for the reaction in part (a), showing all intermediates and electron movement with arrows.
The alkene shown undergoes bromination. H (a) Draw the product(s) of bromination of this compound, including all expected stereoisomers (if any). Use wedge-and-dash bonds to designate the stereochemistry at any chirality centers, and make sure to draw an explicit hydrogen if a chirality center has one. (b) Characterize the starting alkene as having the E or Z configuration. (c) characterize the product(s). (a) H Br₂ Draw the product(s) of bromination. Br H Br
When treated with NaOH, the bromide below gives an alkene by the E2 mechanism, by eliminationof the circled atoms: (a) Draw the Newman projection from which elimination takes place. (b) Draw the mechanism. (c) Draw the product with the proper stereochemistry. (d) Assign the proper stereochemical descriptor to the product. (Z, E? Trans,CiS?) (e)What would happen to the stereochemistry of the product if the enantiomer of the starting material were used inthe reaction?