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- 1. Methylene cyclohexane, on treatment with strong acid, isomerises to yield methyl cyclohexene. Propose a mechanism by which the reaction might occur.Predict the product(s) for each of the following elimination reactions. In each case show the mechanism. What do the mechanisms have in common? Why? OH H2SO4 (a) (b) Cl CH3 -OH CH3 H (c) CS Scanned with CamScanner CH3CO2Na CH3CO2H H2SO4 3Provide the reagent and mechanism for the transformation below. Explain in detail how the reaction conditions provide the given regioselectivity observed in the product.
- Predict the product(s) for each elimination reaction below. In each case show the mechanism. What do the mechanisms have in common? Why? (b) (c) CI CH3 CH3ONa CH3OH Br (CH3)3COK THE x OTos CH3ONa CH³OHGive the mechanism of the following reactions. Briefly explain why any selectivities occur. 1 eq HBrIn the presence of an appropriate base, esters undergo self-condensation to afford the corresponding B-ketoesters as shown below. Explain in detail using reaction schemes (not mechanisms) why route C and not routes A and B would lead to the expected product. 2 x Ethyl acetate A: NaOH(aq) B: OMe- C: OEt- EtO CH3
- Predict the product(s) and provide the mechanism for each reaction below.A step in a synthesis of PGE1 (prostaglandin E1, alprostadil) is the reaction of a trisubstituted cyclohexene with bromine to form a bromolactone. Propose a mechanism for formation of this bromolactone and account for the observed stereochemistry of each substituent on the cyclohexane ring. Alprostadil is used as a temporary therapy for infants born with congenital heart defects that restrict pulmonary blood flow. It brings about dilation of the ductus arteriosus, which in turn increases blood flow in the lungs and blood oxygenation.When cis-2-decalone is dissolved in ether containing a trace of HCl, an equilibrium is established with trans-2-decalone. The latter ketone predominates in the equilibrium mixture. Propose a mechanism for this isomerization and account for the fact that the trans isomer predominates at equilibrium.
- Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.Acid-catalyzed hydrolysis of the following epoxide gives a trans diol. Of the two possible trans diols, only one is formed. How do you account for this stereoselectivity?Draw a structural formula for the major organic product of each reaction and specify the most likely mechanism by which each is formed. (g) CH3CH2ONa++CH2=CHCH2Clethanol