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- The following bicyclic ketone has two -carbons and three -hydrogens. When this molecule is treated with D2O in the presence of an acid catalyst, only two of the three -hydrogens exchange with deuterium. The -hydrogen at the bridgehead does not exchange. How do you account for the fact that two -hydrogens do exchange but the third does not? You will find it helpful to build models of the enols by which exchange of -hydrogens occurs.The trimethylsilyl (TMS) protecting group is one of several silicon protecting groups for alcohols. For each reaction, draw the mechanism for the protection of (R)-3-bromo-1-butanol with the following silyl chlorides, using triethylamine as the base: (a) terf-butyldimethylsilyl chloride (TBS-C1] (b) triisopropylsilyl chloride (TEPS-C1) (c) triethylsilyl chloride (TES-C1)Identify the mechanistic pathways, respectively, for the products in the following reaction. a) E1, SN1 b) E1, SN2 c) E2, SN1 d) E2, SN2
- Please describe the difference in the outcome of treating a terminal alkyne with HgSO4, H2SO4, H2O and with 9-BBN, followed by H2O2 and NaOH.Draw the organic products formed when cyclopentene is treated with each reagent. With some reagents, no reactionoccurs.a. H2 + Pd-Cb. H2 + Lindlar catalystc. Na, NH3d. CH3CO3He. [1] CH3CO3H; [2] H2O, HO–f. [1] OsO4 + NMO; [2] NaHSO3, H2Og. KMnO4, H2O, HO–h. [1] LiAlH4; [2] H2Oi. [1] O3; [2] CH3SCH3j. (CH3)3COOH, Ti[OCH(CH3)2]4, (–)-DETk. mCPBAl. Product in (k); then [1] LiAlH4; [2] H2OAccount for the rapid rate of methanolysis of ClCH2OCH2CH3 even though the substrate is a primary halide. Hint: The reaction of the substrate with ethanol proceeds by SN1 mechanism. Draw the Lewisstructures.
- The Baylis–Hillman reaction is a DABCO (1,4-diazabicyclo[2.2.2]octane) catalyzed reaction of an a,b-unsaturated carbonyl compound with an aldehyde toform an allylic alcohol. Propose a mechanism for the reaction. (Hint: DABCO serves as both a nucleophile and as a base in the reaction.)True or false SN1 substitution reactions involve a carbanion intermediate.Q4 Which statement below about Sn1 reactions is incorrect? (A) SN1 reactions are stepwise and have intermediates. (B) The slow step in a SN1 reaction is formation of the carbocation intermediate. (C) SN1 reactions have first order kinetics which means only the alkyl halide is involved in the rate limiting step. (D) The products of a SN1 reaction will be a pair of enantiomers. (E) An aprotic solvent is best for Sn1 reactions as they tend to help stabilize carbocation intermediates.
- Which of the following is a substrate product when benzene is first treated with HNO3 and H2SO4, and THEN treated (in a second step) with Br2 and FeCl3 (or FeBr3)? 1-bromo-3-nitrobenzene 1-chloro-1-nitrobenzene 1-bromo-1-nitrobenzene aniline cis-1-bromo-2-nitrocyclohexaneWhat is the best set of reagents to achieve deoxygenation of 2-pentanone to pentane? A. NaClO2/NaH2PO4 B. LiAlH4, Et2O C. DIBAL-H, THF D. NH2NH2/t-BuOK, DMSOThe Baylis–Hillman reaction is a DABCO (1,4-diazabicyclo[2.2.2]octane) catalyzed reaction of an a,b-unsaturated carbonyl compound with an aldehyde to form an allylic alcohol. Propose a mechanism for the reaction. (Hint: DABCO serves as both a nucleophile and as a base in the reaction.)