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C. d. e. not a.-d. 15. Assumin g a large excess of benzene, what is the major pr

ID: 549232 • Letter: C

Question

C. d. e. not a.-d. 15. Assumin g a large excess of benzene, what is the major product of the following reaction? AlCI a. b. C. e. not a.-d. 16. The Wolff-Kishner reaction is a how many electron reduction? Hint: Analyze the starting material and product. a. b. 4 d. 8 e. not a.-d. C. 17-19. Starting with benzene, complete the following reaction sequences. Assume any necessary workup. Answers may be repeated. 17. Cl/FeCls, NaNH2, NaNO2/HCl/cold, CuoH, NaoH/CO2 C 18. Ch/F Feclb, HNO:/H2S0, (continue with minor product), NaoH, H2/Pd, NaNO:/HCl/cold, CuCN, Ho D d. not a.-c. b. C. 20. Which substitution mechanism is not used in any of the syntheses of questions 17.-19.? d. radical e.S c. nucleophilic aromatic a. benzyne b. electrophilic aromatic

Explanation / Answer

15. answer is option d. This is fridel-crafts alkylation, usually benzene is used excess for complete reactivity of the reaction mixtures. the major product is d, carbon cation is more stable in d.

16. Wolf-Kishner reaction is basically redcution of ketones to alkanes. 2 electrons are reduced. a

17. option a

benzene+FeCl3/Cl2 gives chlorobenzene, then NaNH2 gives aniline (chlorine is substituted by NH2); then NaNO2/HCl/cold gives phenol then reaction with CuOH / NaOH/CO2 gives a

18. option a

benzene+FeCl3/Cl2 gives chlorobenzene, then nitration reaction with HNO3/H2SO4 gives 2-chloronitrobenzene as a minor product and 4-chloronitrobenzene as major product. So, continue with minor product then reaction with NaOH gives 2-nitrophenol. reaction with Pd/H2 reduces the nitro group in the reactant giving 2-aminophenol as product. then reaction with NaNO2/HCl/cold and CuCN gives 2-cyanophenol. Finally, hydrolysis with H3O+ gives the product a

19. option d

benzene + HNO3/H2SO4 gives nitrobenzene; then nitrobenzene on reaction with cl2/FeCl3 gives meta-chloronitrobenzene; reaction with Pd/H2 reduces the nitro group in the reactant giving meta-aminochlorobenzene as product. then reaction with NaNO2/HCl/cold and CuCN gives 2-cyanochlorobenzene. Finally, hydrolysis with H3O+ gives the product 2-chlorobenzoic acid.

20. radical mechanism

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