Predict in order of reactivity (1 being the slowest, 3 being the fastest) of primary, secondary, and tertiary alkyl halides toward nucleophilic displacement by an SN2 reaction mechanism
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- Rank the nucleophiles in following group in order of increasing nucleophilicity. H2O, −OH, CH3CO2-Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.Pleas explain how this process occurs. Identify SN1, SN2, E2, E1, nucleophiles and electrophiles.
- Rank the following compounds in order of increasing reactivity in a substitution reaction with −CN as nucleophile.Draw reaction mechanisms with all reactants, arrows, intermediates, and products. Your mechanism must account for all the products if more than one product is formed. 4-methycyclohexanol with phosphoric acid H3PO4 to for 1-methycyclohexene, 3- methylcyclohexene and 4-methycyclohexeneBr Brz CH3 CH3 H3C CH2CI2 H3C Br Electrophilic addition of bromine, Br2; to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl). In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br: :Br: .CH3 H3C H3C CH3 Br:
- Complete each reaction scheme below with the starting material required to give the product shown as the only major product following the indicated sequence of reactions. Each individual reaction in the sequence must serve a purpose and must result in a product that is different from the corresponding starting material. 1) i) LIAIH, ii) H30* 2) TSCI, pyridine OTsProvide the reagents and mechanism for each step of the synthesis.Select the reagent that you would use to convert an alkene to an epoxide. mCPBA 03, then DMS BH3-THF, then H2O2, H2O, NaOH Hg(OAc)2, H2O, then NaBH4
- OH of H H H3C- Dess-Martin periodinane provides a means to oxidize a primary alcohol to an aldehyde, while avoiding the use of toxic Cr(VI) compounds. The mechanism involves a reaction similar to the E2 elimination, whereby a C=O double bond is formed with a reduced iodine compound as the leaving group. The reaction occurs in a nonaqueous solvent, CH₂Cl₂, so that the aldehyde product can be recovered. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions AOC XT OAc AcO -OAc & A H3C H H AcO CH3 H -OACH OAC ACO CH3 -OAc H Асӧн етаb) Listed below are several hypothetical nucleophilic substitution reactions. None is synthetically useful because the product indicated is not formed at an appreciable rate. In each case provide an explanation for the failure of the reaction to take place as indicated. OMe HO + OMe + OH HO + CH; OH1) Provide the reagent(s) and the reaction mechanism of the following reaction. H₂N