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- Treatment of 1-aminoadamantane, C10H17N, with methyl 2,4-dibromobutanoate in the presence of a nonnucleophilic base, R3N, involves two successive SN2 reactions and gives compound A. Propose a structural formula for compound A.Propose a mechanism to account for the formation of 3, 5-dimethyl- pyrazole from hydrazine and 2, 4-pentanedione. Look carefully to see what has happened to each carbonyl carbon in going from starting material to product.Show the products from the reaction of p-bromoaniline with following reagents: a)CH3Cl(excess) b) HCl c) CH3COCl d) CH3MgBr e) CH3CH2Cl, AlCl3
- Boron tribromide (BBr3) cleaves ethers to give alkyl halides and alcohols.R¬O¬R′ + BBr3 ¡ R¬O¬BBr2 + R′BrR¬O¬BBr2 + 3 H2O ¡ ROH + B(OH)3 + 2 HBrThe reaction is thought to involve attack by a bromide ion on the Lewis acid–base adductof the ether with BBr3 (a strong Lewis acid). Propose a mechanism for the reaction ofbutyl methyl ether with BBr3 to give (after hydrolysis) butan-1-ol and bromomethane.8.b)Provide mechanisms for the following reactions:Undecanal is commercially available, but 6-methyl-1-bromoheptane is not. Propose two methods for the synthesis of 6-methyl-1-bromoheptane using precursors containing fewer than five carbon atoms (Cn n < 5). A protecting group will probably be required.
- Predict the products formed when cyclohexanone reacts with the following reagents. h) sodium acetylide, then mild H3O+Predict the products of the reaction with benzaldehyde with the following reagents? NaBH4, then H3O+ Dess_Martin reagent Methylmagnesium bromide, then H3O+ (C6H5)3P=CH2a)Write the SN2 reaction mechanism between iodobutane with sodium hydroxide, NaOH. b)Predict the products and show the SN1 reaction mechanism that occurs with 2-iodo-2- methylpropane in aqueous sodium hydroxide, NaOH.
- The base-promoted rearrangement of an a-haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2-chlorocyclohexanone to cyclopentanecarboxylic acid. Jo Han Sow La NaOH, THF O Nat H3O+ OH NaOH, THF The mechanism involves the following 5 steps: -ō cyclopropanone intermediate 1. Abstraction of a proton to form enolate anion 1; 2. Formation of a cyclopropanone intermediate 2 with expulsion of chloride ion; 3. Addition of hydroxide ion to form tetrahedral intermediate 3; 4. Collapse of the tetrahedral intermediate and breakage of the three-membered ring to form carbanion intermediate 4; 5. Proton transfer to form the rearranged carboxylic acid. For the following reaction, draw the reaction out on paper, and then draw the structure of cyclopropanone intermediate 2 in the window. 1. NaOH, THF 2. H3O* OHPredict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents. (d) anisole and aluminum chloride (e) excess phenylmagnesium bromide, then dilute acid (f) LiAlH(O@t@Bu)3provide a 5-step synthesis to arrive at the final structure. Provide intermediate steps and show arrow pushing mechanism. Please use the following reagents: 1. Mg, Et2O 2. Formaldehyde 3. Cr(IV) 4. SOCl2 5. 2 eq of HN(Et)2