(a) Which carbonyl compounds would CH3 CH3CH,CH2CH,CCH,OH (b) HyÇ OH (e) you reduce to produce the following CHC- CHCH CHCH,Ch alcohols? List all possibilities.
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- What steps are needed to prepare phenylacetylene, C6H5C = CH, from each compound: (a) C6H5CH2CHBr2; (b) C6H5CHBrCH3; (c) C6H5CH2CH2OH?Determine whether each of the following syntheses requires a reaction that alters the carbon skeleton. (a) (b) OH (c) (d) OCH,CH3 CH3 (e) OH (f) H,CO он H;CO. (g) H3CO, (h) H3CO. NO2 NO2Provide the structure of the product(s) with stereochemisty if appropriate. If multiple products indicate major product or if products are formed in equal amounts. If there is no reaction expected explain why. (a) OH HIO4 (the protecting group is remained) CHO H HOH2C OH (b) CHO -ОН NaCN # HO -H H -OH CH₂OH (c) CHO HO- -H HO -H NH₂OH 張一 H -OH H -OH CH₂OH i) Ba(OH)2 ii) MeOH, H₂SO4 NaOAc Ac₂0 NaOMe MeOH
- A molecule of propanone reacts with an cyclohexylethanone in presence of aq. NaOH to combine together, and the resulting product is boiled to produce another product, (i) CH3 -NH2 НО H;COThe key step in a reported laboratory synthesis of sativene, a hydrocarbon isolated from the mold Helminthosporium sativum, involves the following base treatment of a keto tosylate. What kind of reaction is occurring? How would you complete the synthesis?(a) (b) HO N N-H Catalytic H+ (-H₂O) ? (c) NH2 HO N (d)
- 4 Which of the following alcohols could not be made selectively by hydroboration-oxidation of an alkene? Explain. about the (b) (a) (c) OH | CH3CH₂CH₂CHCH3 In H OH (CH3)2CHC(CH3)2 (d) CH3 vino zbiory 1 OH o no atou OH vollot edt evig H noituloa siblos V H но но CHO SHO=3₂HƆ m² CH3s 10 out of ST bewollot giaylonoso no WBTⱭ 12-8 His to edustrie 5 wode, $2-8 OnMX dilw osviel vitabPredict the products formed when CH3CH2¬C‚C≠- Na+ reacts with the following compounds.(a) ethyl bromidePredict the products formed when CH3CH2¬C‚C≠- Na+ reacts with the following compounds.(a) ethyl bromide (b) tert-butyl bromide(c) formaldehyde
- Explain why each of the following carboxylic acids cannot be prepared by a malonic ester synthesis: (a) (CH3CCH;COOH; (b) C,H;CH2COOH; (c) (CHa)CCOOH.Predict the products formed when CH3CH2¬C‚C≠- Na+ reacts with the following compounds.(a) ethyl bromide (b) tert-butyl bromide(c) formaldehyde (d) cyclohexanone(e) CH3CH2CH2CHO1. How would you prepare the following alkyl halides from the appropriate alcohols? (a) ÇI (b) Br CH3 CH3CH3 CH;CHCH,CHCH3 ČH3 2. Predict the products of the following reaction: (a) он CH3 (b) H2C CH;CH,CHCH,CHCH, Per, socl2. PBr3 ? H3C