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- 8.30 For each of the following alkenes, draw the structure of two different alkyl halides that yield the given alkene as the only product of dehydrohalogenation. a. b. EX C.7.45 Draw the products of each nucleophilic substitution reaction. а. + CI NACN b. С. + H20 d. HO. CI Br е. NaOCH3 CI f.Problem 8.16 Draw both the SN1 and E1 products of each reaction. of Br + H20 b. HO, a. CI
- Problem 8.20 Which mechanism, E1 or E2, will occur in each reaction? to b. + OCH₂ - + H₂O - 1 . d. + CH₂OH Br -OC(CH3)3What product is formed when each compound undergoes thermal electrocyclic ring opening or ring closure? Label each process as conrotatory or disrotatory and clearly indicate the stereochemistry around tetrahedral stereogenic centers and double bonds. а. b.Problem 8.2 Classify each alkene in the following vitamins by the number of carbon substituents bonded to the double bond. OH b. vitamin A vitamin D, HO
- What product is formed by the [3,3] sigmatropic rearrangement of each compound? a. b.9.44 Draw the products of each reaction and indicate stereochemistry around stereogenic centers. a. b. C. d. e. f. OH HD OH OH OH OH OH HBr HCI ZnCl₂ SOCI₂ pyridine TSCI pyridine HBr HCI KI7.61 Draw a stepwise mechanism for the following reaction that illustrates how two substitution products are formed. Explain why 1-bromohex-2- ene reacts rapidly with a weak nucleophile (CH3OH) under SN1 reaction conditions, even though it is a 1 ° alkyl halide. OCH3 CH;OH Br OCH3 + HBr 1-bromohex-2-ene
- 8.45 Which of the following compounds undergoes E2 elimination with strong base? For compounds that undergo elimination, draw the product. For compounds that do not undergo elimination, explain why they are unreactive. а. Br b. Br с. Br H.Problem 8.21: Draw all the stereoisomers of 3-bromo-4-methylhexane. a. How many stereoisomers can you draw? Classify the stereoisomers as enantiomers and diastereomers. b. Consider E2 elimination across C3-C4 bond for all stereoisomers. How many alkene products can you draw and how are they related to each other? Problem 8.22: Rank the following alkyl halides in decreasing order of reactivity towards E2 reaction (most reactive -3 and least reactive -1). a. b. Br Br CH3 CH(CH3)2 Br CH3CH2OH Br CH3 CH(CH3)2 CH(CH3)2 Problem 8.23: The following reaction is an E1 reaction. Draw and energy diagram to represent the reactants, products and intermediate. Xor CH3 + Br Br8.64 Reduction of butan-2-one with NaBH4 yields butan-2-ol. Explain why the product is chiral but not optically active. CH3CCH2CH3 Butan-2-one