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1. a) Provide a complete and detailed reaction mechanism for the following reaction. Include at least two possible termination steps. Don't forget to use fishhook arrows! H₂C-CH3 + Part A - Chapter 10- Haloalkanes Br₂ hv H₂C-CH₂Br + HBr
b) Calculate AH (heat of the reaction) for each of the propagation steps. c) Based on the values you got on part b draw and label the reaction-energy diagram for the propagation steps from part a. Label the axes. Label all of the energy maxima and energy minima on the respective curves with the structures of the appropriate reactants, transition states (show partial bonds as dotted lines), intermediates, and products. Label the AH (heat of the reaction) for each step and also for the general reaction. A
O 2. For each of the following cases draw the radical that you would expect to be formed by the hydrogen abstraction with bromine radical. X b) c) d) + Br Br - Br H W
3. a) In chapter 11 we are going to learn how alkyl halldes react, so it is important that you know how to prepare alkyl halldes. So far we have learned how to convert alkanes and alkenes Into alkyl halides. For the following reactions draw all the reagents necessary to convert starting material to product. Make sure that you understand these reactions. 8) Me Me b) b) In chapter 17 you are going to learn how alcohols react, so it is important that you know how to prepare alcohols. So far we have learned how to convert alkenes Into alcohols by 3 different ways. Me For the following reactions draw all the reagents necessary to convert starting material to product. Make sure that you understand these reactions. OH - Me Br :-8 Me
Part B-S1/S2, E1/E2 1. For the following reactions, write the major product, showing the stereochemistry. Write the names for mechanism, Le. S1/S2, E1/E2. a) b) Me CI K Br Br OH + CH₂SNa EtOH + CH,CH,O-Na* + NaN, CH₂CH₂OH EtOH 2
2. For the following compounds Indicate if they will react under S1 conditions (solvolysis with EtOH), S2 conditions (KI/acetone), both, or nelther. Write the producte and by which mechaniem they are produced. ☆ b) Me COMe Br Part C-Elimination In order to solve problems involving elimination reactions, you have to clearly understand the mechanism: so review the mechanism for E1 and E2 reactions before you start. 3) Which Isomer would you expect to react faster under E2 elimination conditions: trans-1-bromo-4-tert-butylcyclohexane or cis-1-bromo-4-tert-butylcyclohexane? Draw each molecule in its more stable chair conformation and explain your answer. 2) Predict the major product obtained in the following reactions.
For the problem r draw Newman projections in order to show how you obtained your product. You do not need to draw the mechanism for all of them but you must know the mechanism, so it is a good idea to draw the mechanism for at least one E2 and one E1 reaction. a) 6 d) Br C Br Me Me Br Br CH₂CH₂ONS CHICHSONG CHI CHIỐNG H₂O CH₂CH₂OH, A CH₂O²Na (CH3500-x+ 0x0 CH₂CH₂O'Ns E
Part D-Synthetic Transformatione In order to solve these problems you have to clearly understand the mechanisms. 1) Show how you might bring about the following conversions. For any conversion Involving more than one step, show each Intermediate compound formed. As you may realize there is no space in this page, so please solve these problems in a separate page. a) the ·0-0° ہے۔ OH ·0-X OH 4
2) Provide the synthesis of compounds I and II. The pool of carbon-containing starting materials that you can use is shown in the square brackets. You may use any other common reagents. A retrosynthetic analysis will help you to figure out these problems. If you show a valid retrosynthesis you will get partial credit even if the synthesis Is Incomplete. wogr Fama HỌ CH Compound I Compound II M