H Benzaldehyde Br. bromoaldehyde 1. Mg, ether + Br. 4-Bromobutanal H OH H 5-Hydroxy-5-phenylpentanal (racemic) OH H+ Br. H + HO diol Q-MgBr+ HCl, H₂O A cyclic acetal +H.O OH H OH + HO 2. C6H5CHO A chiral magnesium alkoxide (produced as a racemic mixture) 5-Hydroxy-5-phenylpentanal (formed as a racemic mixture)
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Illustrate the mechanism or synthesis for the following reaction. Show all steps.
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- H3C OH OH CH3 1,3-pentanediol + B OMe OME OME MeO... CH3 H3C OMe benzaldehyde dimethylacetal catalytic Me 0:0 OH FO (p-TsOH) CH3CN H... MeO, OMe OMe e a & H3C CH3 H3C CH3 H3C CH3 C D A HO E HO OCH3What product(s) is(are) formed in the following reaction Br/CH-Clz Br plus enantiomer H3C Et Br Br H and H3C Br H3C Et Et Br он ...Et plus enantiomer H3C BrDraw the products formed when p-methylaniline (p-CH3C6H4NH2) is treated with each reagent.a. HClb. CH3COClc. (CH3CO)2Od. excess CH3Ie. (CH3)2C = Of. CH3COCl, AlCl3g. CH3CO2Hh. NaNO2, HCli. Part (b), then CH3COCl, AlCl3j. CH3CHO, NaBH3CN
- 26. Give the major organic product of each reaction. Indicate if a racemic mixture is expected. Br OH Br₂ Br₂ a. b. H₂O raumic racenie CH30 OH Br2 ICHS a. Br2, H₂O C. d. CH3OH b. NaH Br racemic racer Cl e. Cl₂ JOH OH f. a. Cl₂, H₂O b. NaH race1. Assign E or Z to the following alkenes. If the alkene does not have stereochemistry, write "NONE". H CI H3C SH T. H CI, ОН H3CH2C НО D D EN C(CH3)3 CH3 Me H Et N' 'N' C=C H3C Et Me what Columbus sought in the 'Indies' - Piperine CH2OH Br (H3C);C, H3C HOH, CH,CF, H3C Br HOH2C НО H the spice Columbus found (Capsaicin) HO. Muscalure Bombykol (the sex attaractant for the male silkworm) (the sex attaractant for the common housefly) OH .CO2H the "heart healthy" part of olive oil a 'less healthy' trans fatty acid from trans fatselect reagents: cyclopentanone Reagents a. C6H5CHO b. NaOH, ethanol c. Pyrrolidine, cat. Hj. d. H₂C=CHCN e. H3O+ f. LDA g. A) bg EtOC(=O)CO₂Et h. i. B) ka k. I. m. O: BrCH₂CH=CH₂ NatOEt, ethanol Br₂, H+ K+ t-BUO™ CH2(CO2Et)z heat C) jh CO₂Et D) Im
- Give the organic reaction products for the following reaction a. b. a. b. CH3CH2-C. ง ว NaOH ? + ? N(CH3)2 H₂O H*/H₂O CH3-C-OCH2CH3 ? + ?Give the organic product. dy I. II. OA I D. VV MeO₂C NaOMe CO₂Me CO₂Me P Note: Me= CH3 III. IV. OMe ço,Me15. Give the major organic product, paying attention to stereochemistry (syn/anti). Indicate if a racemic mixture is expected. a. a. BH3 b. H2O2, OH a. BH3 b. b. H2O2, OH a. BH3 a. BH3 C. d. b. H2O2, OH b. H₂O2, OH e. a. BH3 b. H₂O2, OH
- These reagents can produce ketones with alkynes A. BH3, THF, H2O2 B. KMnO4 C. O3 D. H2SO4, H2O, HgSO4Draw the organic products formed when cyclopentene is treated with each reagent. With some reagents, no reactionoccurs.a. H2 + Pd-Cb. H2 + Lindlar catalystc. Na, NH3d. CH3CO3He. [1] CH3CO3H; [2] H2O, HO–f. [1] OsO4 + NMO; [2] NaHSO3, H2Og. KMnO4, H2O, HO–h. [1] LiAlH4; [2] H2Oi. [1] O3; [2] CH3SCH3j. (CH3)3COOH, Ti[OCH(CH3)2]4, (–)-DETk. mCPBAl. Product in (k); then [1] LiAlH4; [2] H2O[Review Topics] [References] HO pyridine 1. SOCIl, + sO2 + H. Aqueous acetone H3C H20 H3C HBr 2. Br H OH optically active racemic f = SN1 Nucleophilic substitution g = SN2 Nucleophilic substitution a = Proton transfer d = E1 Elimination b = Lewis acid/base e = E2 Elimination c = Electrophilic addition The rections above involve synthesis or reactions of alcohols and ethers. Identify the mechanism by which they proceed from among the mechanisms listed. Use the letters a - g for your answers. 1. 2.