An a,ß-unsaturated carbonyl compound can be prepared by a reaction known as a selenenylation-oxidation reaction. A selenoxide is formed as an intermediate. Propose a mechanism for the reaction. 1. LDA/THF 2. CgH5SeBr 3. H,02 ŠECH5 a selenoxide
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- The Baylis–Hillman reaction is a DABCO (1,4-diazabicyclo[2.2.2]octane) catalyzed reaction of an a,b-unsaturated carbonyl compound with an aldehyde toform an allylic alcohol. Propose a mechanism for the reaction. (Hint: DABCO serves as both a nucleophile and as a base in the reaction.)The Baylis–Hillman reaction is a DABCO (1,4-diazabicyclo[2.2.2]octane) catalyzed reaction of an a,b-unsaturated carbonyl compound with an aldehyde to form an allylic alcohol. Propose a mechanism for the reaction. (Hint: DABCO serves as both a nucleophile and as a base in the reaction.)The poison gelsemoxonine can be isolated from the leaves of a plant native to southeastern Asia (Gelsemium elegans). A key step in a synthesis of this natural product involves a thermally initiated (70°C) sigmatropic rearrangement of the compound shown below (R=protecting group) (J. Am. Chem. Soc. 2011, 133, 17634–17637). Draw the curved arrows for the mechanism of the formation of gelsemoxonine. Include lone pairs in your answer.
- Chemistry Draw the product formed when phenylacetaldehyde (C6H5CH2CHO) is treated with reach reagent: f. (CH3)2CHNH2, mild acid g. (CH3CH2)2NH, mild acid h. CH3CH2OH (excess), H+ i. piperidine, mild acid j. HOCH2CH2OH, H+Which of the following statements about terminal alkynes is FALSE?I I. A geminal dihalide is produced by the hydrohalogenation reaction.II. The proton in the terminal carbon is acidic but just slightly.III.They create an aldehyde when they react with H2O, H2SO4, and HgSO4.IV. A silver acetylide is formed after treatment with alcoholic AgNO3.These reagents can produce ketones with alkynes A. BH3, THF, H2O2 B. KMnO4 C. O3 D. H2SO4, H2O, HgSO4 choices:A,DB,CA,B,CA,B,C,D
- 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 alkylatingagent.(b) Bleach (sodium hypochlorite, NaOCl, a strong oxidizing agent) neutralizes and inactivates mustard gas. Bleach is also effective on organic stains because it oxidizes coloredcompounds to colorless compounds. Propose products that might be formed by thereaction of mustard gas with bleach.This is Wittig Rxn: Whatever mechanism you choose to draw is fine since you can leave the base as B: Draw the arrow pushing mechanism using the compounds below – Constant: 4-nitrobenzyl benzaldehydebase 1: triethylaminebase 2: NaOHbase 3: K2CO3ylide: Acetonyltriphenylphosphonium chloridePropose 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.
- 8. Propose a mechanism for this transformationWhat is the major product of the reaction of 1 mol of propyne with each of the following reagents? a. HBr (1 mol) e. aqueous H2SO4, HgSO4 h. H2/Lindlar catalyst b. HBr (2 mol) f. R2BH in THF followed by i. sodium amide c. Br2 (1 mol)/CH2Cl2 H2O2/HO-/H2O j. the product of part i followed by d. Br2 (2 mol)/CH2Cl2 g. excess H2, Pd/C 1-chloropropaneBoron 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.
