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- The reaction of 1-iodopropane with potassium thiocyanate (KSCN) in certain solvents results in the formation of two isomeric products, propylthiocyanate and propylisothiocyanate (see scheme below), via the SN2 reaction mechanism. Attempts to prepare a similar mixture of these same isomeric products (propylthiocyanate and propylisothiocyanate) starting from 1-propene is illustrated below. Despite the strong acidity of thiocyanic acid (recall pKa = 1.1), this addition reaction does not lead to either of the products indicated. Based on your knowledge of alkene addition reactions, explain this experimental result.Predict the final product(s) obtained when (2R,3R)-2-bromo-3-methylpentane is subjected to the following sequence of reactions, briefly explaining your rationale. For each step, provide the stepwise mechanism and the regiochemical and stereochemical details as relevant. 1. NaOC2H5/C2H5OH, heat 2. BH3, THF 3. H2O2, OHObtain derivatives or oxidation-reduction products from acetophenone (C6H5COCH3) in four different ways using suitable reagents and appropriate reactions. Write down the mechanism of the one you want in detail.
- Reaction of -pinene with borane followed by treatment of the resulting trialkylborane with alkaline hydrogen peroxide gives the following alcohol. Of the four possible cis,trans isomers, one is formed in over 85% yield. (a) Draw structural formulas for the four possible cis,trans isomers of the bicyclic alcohol. (b) Which is the structure of the isomer formed in 85% yield? How do you account for its formation? Create a model to help you make this prediction.3 Give mechanisms for the acid-catalyzed and base-promoted alpha-halogenation ofketones. Explain why multiple halogenations are common with basic catalysis andgive a mechanism for the haloform reactionComplete the following mechanism for the acid-catalyzed rearrangement of 1-vinyl-2-phenylcyclopropane to give both isomers (E / Z) of 5-bromo-5-phenyl-2-pentene employing the curved-arrow/arrow-pushing formalism.
- A certain hydrocarbon, C7H10, yields the two products shown below upon oxidative cleavage with KMnO4/H3O+ . Deduce the structure of the hydrocarbon.(a) Propose a mechanism for the conversion of cis-hex-3-ene to the epoxide (3,4-epoxyhexane)and the ring-opening reaction to give the glycol, hexane-3,4-diol. In your mechanism, payparticular attention to the stereochemistry of the intermediates and products.(b) Repeat part (a) for trans-hex-3-ene. Compare the products obtained from cis- andtrans-hex-3-ene. Is this reaction sequence stereospecific?On being heated with a solution of sodium ethoxide in ethanol, compound A (C7H15Br) produced a mixture of two alkenes B and C, each of which had the molecular formula C7H14. Catalytic hydrogenation of major isomer B or minor isomer C gave only 3-ethylpentane. Suggest structures and mechanisms for compounds A, B, and C consistent with these observations.
- write the mechanism and predict the product, and includ the stereochemistryGive the structure of the product and/or intermediates of the following reactions. Indicate, where appropriate, both regiochemistry and stereochemistry.(S)-2-Butanol, CH3CH2CHOHCH3, slowly racemizes on standing in dilute aqueous sulfuric acid. Explain, illustrating with a mechanism.