The tosylate of (25,35)-3-phenylbutan-2-ol undergoes an E2 elimination on treatment with sodium ethoxide. Draw the structure of the alkene that is produced. Use the wedge hash bond tools to indicate stereochemistry where it exists. You do not have to explicitly draw H atoms. If a group is achiral, do not use wedged or hashed bonds oa it.
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- Draw the structures of the product from each of the following reactions and then answer the questions about the isomeric relationships between compounds A, B, and C. You must indicate the stereochemistry in the products (wedge/dashed bonds). SOCI, NaOCH3 pyridine NaOCH; OH B TSCI NaOCH3 pyridine TSCI = p-toluene sulfonyl chloride C a. What is the relationship between products A and B? (identical, enantiomers, structural isomers) b. What is the relationship between products A and C? (identical, enantiomers, structural isomers)Write the structure of the key intermediate and the product (with correct stereochemistry) for the reaction of N-Bromosuccinimide (NBS) with cyclopentene in aqueous DMSO NBS DMSO O°H Intermediate ProductDraw the structure of the product obtained when this amine is treated with excess iodomethane and then heated with Ag₂O (Hoffman elimination). ball & stick v + labels • Consider E/Z stereochemistry of alkenes. • Draw only the elimination product, do not the leaving group. • In cases where there is more than one answer, just draw one.
- The reaction of 2-ethyl-1-pentene with Br2, with H2 + Pd/C, or with R2BH/THF followed by aqueous HO- + H2O2 leads to a racemic mixture. Explain why a racemic mixture is obtained in each case.Draw the structural formula of the major product of the reaction of (S)-2,2,3-trimethyloxirane with Me,NH. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Include H atoms at chiral centers only. • If a group is achiral, do not use wedged or hashed bonds on it.Complete the synthesis of ethyl (E)-2,2,4-trimethyl-3-oxo-5-phenylpent-4-enoate from the starting material given (ethyl propionate). You must list out all reagents/solvents next to the reaction arrows and draw the intermediate structures in the boxes. I am giving you one restriction. You are not allowed to introduce any enolates as reagents next to the reaction arrows.
- Complete the synthesis of ethyl (E)-2,2,4-trimethyl-3-oxo-5-phenylpent-4-enoate from the starting material given (ethyl propionate). You must list out all reagents/solvents next to the reaction arrows and draw the intermediate structures in the boxes. I am giving you one restriction. You are not allowed to introduce any enolates as reagents next to the reaction arrows. orff ionThe following nucleophilic substitution occurs with rearrangement. Suggest a mecha- nism for formation of the observed product. If the starting material has the S configura- tion, what is the configuration of the stereocenter in the product? NaOH OH H,0Draw the structure of the product obtained when this amine is treated with excess iodomethane and then heated with Ag20 (Hoffman elimination). ball & stick + labels • Consider E/Z stereochemistry of alkenes. • Draw only the elimination product, do not the leaving group. In cases where there is more than one answer, just draw one.
- Qa 18. Bromination of 5a-cholestan-3-one occurs at C-2 or C-4 to give 2 regioisomers. Two unsaturated ketones with lambdamax = 230 nm and lambdamax = 241 nm are yielded during dehydrobromination. Use Woodward-Fieser rules to distinguish between the two.22. Explain why the following compound cannot be converted to a Grignard reagent. How would you resolve this problem? O & Br O A dimer would form; treat C=0 with diol in acid Mg would react with C=0; treat C=0 with diol in acid A dimer would form; treat Br with diol in acid O Mg would react with C=0; treat Br with diol in acid MgBrWhen pure (S)-lactic acid is esterified by racemic butan-2-ol, the product is 2-butyl lactate, with the following structure:H+CH3 CH COOH CH3 CH CH3 CH CHOH OHCH2CH3 CH2CH3lactic acidC OOH CH O 3butan-2-ol 2-butyl lactate+(a) Draw three-dimensional structures of the two stereoisomers formed, specifying the configuration at each asymmetriccarbon atom. (Using your models may be helpful.)(b) Determine the relationship between the two stereoisomers you have drawn