CH₂CH₂CN 3-phenylpropanenitrile Electrophilic bromination of 3- phenylpropanenitrile occurs preferentially at the ortho and para positions. Assuming substitution at the para position, draw the structure of the most important resonance contributor of the carbocation intermediate.
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- Rank the compounds in each group in order of increasing reactivity in nucleophilic acyl substitution. C6H5CO2CH3, C6H5COCl, C6H5CONH2Mustard gas, Cl¬CH2CH2¬S¬CH2CH2¬Cl, was used as a poisonous chemical agentin World War I. Mustard gas is much more toxic than a typical primary alkyl chloride. Itstoxicity stems from its ability to alkylate amino groups on important metabolic enzymes,rendering the enzymes inactive.(a) Propose a mechanism to explain why mustard gas is an exceptionally potent alkylatingagentWhich of the following compounds will react with methylamine to form the imine shown below? N.
- Propose a mechanism for the reaction of benzyl acetate with methylamine. Label theattacking nucleophile and the leaving group, and draw the transition state in which theleaving group leaves.Rank the following compounds in order of increasing reactivity in a substitution reaction with −CN as nucleophile.The Stork reaction is a condensation reaction between an enamine donor and an α,β-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of formation of an enamine from a ketone, Michael addition to an α,β-unsaturated carbonyl compound, and hydrolysis of the enamine in dilute acid to regenerate the ketone. Consider the Stork reaction between cyclohexanone and propenal Draw the structure of the product of the enamine formed between cyclohexanone and dimethylamine. - Michael addition to an α,β-unsaturated carbonyl compound, and - hydrolysis of the enamine in dilute acid to regenerate the ketone.
- Please explain the synthesis. Identify SN1, SN2, E1, E2, nucleophiles and ekectrophiles.Predict the major product of the following reaction and draw it in the space provided. 1) NAOMe Br 2) Meo Ome Br 3) NaOt-Bu 4) HCI, H₂O, heatProvide the mechanism for this reaction (include arrow pushing) ОН 2-lodobenzoic acid K2S2O8 H2SO4 ОН OSO3H ОН 양 diphenyliodonium-2-Carboxylate benzyne
- Rank the reactivity of the compounds below toward nucleophilic acyl substitution by writing the compounds' letters in the proper blanks in the box below. `NH CI Br CH3 CH3 A В C E rank compounds for acyl substitution reactivity most least reactive reactiveStep 4: In an acid-catalyzed epoxide ring opening, the epoxide is first protonated and can then be attacked by weak nucleophiles. H HO: :Nuc Nuc Weak nucleophiles such as water and alcohols can react with the protonated epoxide. One of the main differences between base-catalyzed and acid-catalyzed epoxide ring openings is the regiochemical product expected. In an acid-catalyzed reaction, if one of the epoxide carbons is tertiary and the other primary, the nucleophile will attack at the more substituted carbon. If the epoxide is monosubstituted, the nucleophile will attack preferentially at the primary carbon vs. the secondary carbon. Which reaction will not give the indicated product? N 1. CH,CH,O 2. H₂O OH CH₂CH₂OH, H* N CH₂CH₂OH, H 1 CHICH,O 2. H₂O HO HO H- HIf anhydrides react like acid chlorides with the nucleophiles, draw the products formed when each of the following nucleophiles reacts with benzoic anhydride [(C6H5CO)2O]: (a) CH3MgBr (2 equiv), then H2O; (b) LiAlH4, then H2O; (c) LiAlH[OC(CH3)3]3, then H2O.