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Question 8
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- The following is a retrosynthetic scheme for the preparation of trans-2- allylcyclohexanol. Show reagents to bring about the synthesis of this compound from cyclohexane. OH Br "CH,CH=CH, (racemic)19. (a) Show the structure of all reactants and products for the bromination of 1,2 dimethylcyclopentene. Show the proper stereochemistry of the products. 1,2-dimethylcyclopentene + Br2/CCl4-----> Products (b) Show the mechanism of the reaction in (a) above.Treatment of cis-4-bromocyclohexanol with HO− affords compound Aand cyclohex-3-en-1-ol. Treatment of trans-4-bromocyclohexanol under the same conditions forms compound B and cyclohex-3-en-1-ol. A and Bcontain different functional groups and are not isomers of each other.Propose structures for A and B and offer an explanation for theirformation.
- From the table of available reagents select the one(s) you would use to convert cyclohexanone to the following compound: CH,CH,CO,H Use the minimum number of steps; from one to five are required. List reagents by letter in the order that they are used; example: fa. Reagents Available a. BH3, THF; followed by H₂O₂, OH b. Br₂, CH3CO₂H c. HCN, KCN d. H3O*, heat e. LDA (lithium diisopropylamide) f. NaBH4 g. Na* -CH(CO₂C₂H5) (from CH₂(CO₂C₂H5)2 + Na* -OC₂H5) h. PBr3 i. PhCH₂Br j. Ph3P+--CH₂ k. pyridine, heat I. PhBrOn reaction with HC1, one of the trimethylcyclohexanols shown below furnishes a single product; the other furnishes a mixture of two stereoisomers. Fully explain this observation and show which starting material (A or B) produces which product(s). ОН ОН A ВThe following sequence of steps converts (R)-2-octanol to (S)-2-octanol. Propose structural formulas for intermediates A and B, specify the configuration of each, and account for the inversion of configuration in this sequence.
- 4. How would you carry out the following conversions using suitable reagents? a) b) OH НО.Provide the structure of the missing products or reactants. Show the relevant stereochemistry if necessary. H3C Br H₂O _SH [4© 1 product 2 products (2 isomers) ✓ OH + ?<From the table of available reagents select the one(s) you would use to convert cyclohexanone to the following compound: CH₂ Use the minimum number of steps; from one to five are required. List reagents by letter in the order that they are used; example: fa. Reagents Available a. BH3, THF; followed by H₂O2, OH g. Na* -CH(CO₂C₂H5) (from CH₂(CO₂C2H5)2 + Na* -OC₂H5) h. PBr3 i. PhCH₂Br b. Br₂, CH3CO₂H c. HCN, KCN d. H3O*, heat e. LDA (lithium diisopropylamide) f. NaBH4 j. Ph3P+-CH₂ k. pyridine, heat I. PhBr
- 2. Show all the possible products and provide a reaction mechanism for the following transformations. (a) (b) H₂O -OH ? 3. The following diastereomeric tosylates react with sodium t-butoxide in t-butanol to give different products. Show the major product for each reaction and provide a mechanism that would account for their formation. OTS OTSThe Williamson ether synthesis involves treatment of a haloalkane with a metal alkoxide. Following are two reactions intended to give benzyl tert-butyl ether. One reaction gives the ether in good yield, and the other reaction does not. Which reaction gives the ether? What is the product of the other reaction, and how do you account for its formation? CH3 CH3 (a) CH,CO K* + 1. ČH3 -CH,CI CH,COCH,- + KCI DMSO ČH3 CH3 CH3 (b) -CH,O K* + CH,CI CH,COCH,- + KCI DMSO ČH3 CH3Treatment of propadiene (an allene) with hydrogen bromide produces 2-bromopropene as the major product. This suggests that the more stable carbocation intermediate is produced by the addition of a proton to Br HBr. H2C=C=CH, H3C CH2 a terminal carbon rather than to the central carbon. Propadiene 2-Bromopropene (a) Draw both carbocation intermediates that can be produced by the addition of a proton to the allene. (b) Explain the relative stabilities of those intermediates. Hint: Draw the orbital picture of the intermediates and consider whether the CH, groups in propadiene are in the same plane.