6.24 With methyl, ethyl or cyclopentyl halides as your organic starting material

Question

6.24 With methyl, ethyl or cyclopentyl halides as your organic starting material and using any needed solvents or inorganic reagents, outline syntheses of each of the following. More than one step may be necessary.

(ONLY need problem F, G, and J)

286 CHAPTER 6 IONIC REACTIONS: Nucleophilic substitution and Elimination Reactions of Alkyl Halides 6.24 With methyl, ethyl, or cyclopentyl lides as your organic starting materials and using any needed solvents or inorganic reagents, outline syntheses of each of the following. More than one step may be necessary and you need not repeat steps carried out in earlier parts of this problem. (a) CH3I (e) CH3SH (i) CH3OCH3 (b) SH OMe (c) CH3OH (g) CH3CN (d) OH (h) CN 6.25 Listed below are several hypothetical nucleophilic substitution reactions. None is synthetically useful because the product indicated is not formed at an appreciable rate. In each case provide an explanation for the failure of the reaction to take place as indicated. OH CH (a) HO OH (b) OH

Explanation / Answer

(F) Bromoehtane reacts with HSH/OH- to form ethanethioalcohol

CH3CH2Br + HSH ---OH-------> CH3CH2SH + Br-

(G) When bromo methane is treated with aqueous potassium cyanide, it under goes substitution reaction to form ehtane nitrile.

CH3Br + KCN (aq.) ----------------> CH3CN + KBr

(H) When bromo ethane is treated with aqueous potassium cyanide, it under goes substitution reaction to form Propane nitrile.

CH3CH2Br + KCN (aq.) ----------------> CH3CH2CN + KBr

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