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- Consider the following equilibrium: O || R-C-H + HCN HO OH R-C-H | CN (A) When R = CH3CH2-, Keq = 1. (i) Predict whether Keq should be greater or less than 1 when R = CICH2, and (ii) when R is CH2=CH. Explain. (B) In the case where R is CH2=CH, the cyanohydrin is formed faster but given enough time, another constitutional isomeric C4H5NO product predominates. Explain and write a base-catalyzed mechanism for the formation of the other isomer. Recall that: HO HON NN-Nitrosamines by themselves are not significant carcinogens. However, they are activated in the liver by a class of iron-containing enzymes (members of the cytochrome P-450 family). Activation involves the oxidation of a C-H bond next to the amine nitrogen to a C-OH group. OH ОН N=0 N=O Og 'N- H+ H N,+ cyt P-450 N-Nitroso- 2-Нydroxy-N- nitrosopiperidine An alkyl diazonium ion piperidine (a carcinogen) Show how this hydroxylation product can be transformed into an alkyl diazonium ion, an active alkylating agent and therefore a carcinogen, in the presence of an acid catalyst.c-e only
- CH hyperconjugation A) Present B) AbsentWhich of the following bases are strong enough to deprotonate CH3CH2CH2C≡CH (pKa = 25) so that equilibrium favors the products: NaC ≡ N NaH CF3COONa CH3Li CH3ONa NaNH2For the reaction in the box, what is the structure of the missing reactant? H3C OH OH ? H;CO H,SO4 ÓCH3 A) LOCOCH3 COOCH 3 B) C) D) CH2OCH3 COCH3 O A
- 5-31 Draw the enantiomer, if any, for each structure. (a) COOH (b) CH, (c) СНО (d) HO CH, Br -H H- OH H- OH COOH H- -O- H- OH CH,OHProtonated intermediates are common in more complex organic reactions. Which molecule when protonated is more acidic? (+) +) acetone diethyl ether acetone O diethyl etherDraw a structural formula for the intermediate in the following reaction: CH2CI2 CH;CH=CHCH2CH(CH3)2 Cl2 You do not have to consider stereochemistry. You do not have to exnlicitly dray H atomr
- The structure shown below is an intermediate in the synthesis of which biogenic amine? Use arrows to show how the next intermediate in this reaction is formed, and draw the structure of that intermediate. -CH,-C-coo HN N || CH HO CH,0 H,CWhich of the following exhibit C-H hypeconjugation only? NH2 А В D A and D A and C A DCH;COCH3 is more reactive than CH;CHO towards HCN. (A) True B) False