14.-16. Starting with benzene, match each reaction sequence to a major product b

Question

14.-16. Starting with benzene, match each reaction sequence to a major product below. Assume any necessary workup between steps, which are separated by commas. Answers may be repeated. 14. Clz/AlChs, NaNHb, cold NaNo,/HCI, CuOH, HNO,/H,SO, use the minor product from previous step, Ha/Pd, NaNO/H CuCN, H3O* 15. Clh/AlCls, HSOs, HNO,/H,Soa, HO', NaoH, H2/Pd, cold NaNO,/HCL, H PO, NaOH, CO, Hy0" 16. HNO:/H2SO4, H2/Pd, cold NaNO,/HCI, CuCN, H0', 1-chloropropane/AICh, O, H' catalysis CO HO b. HO CO2H CO2H a. OH C. d. not a.-c. 17. Which reaction sequence from the above questions involves aromatic substitution with electrophilic oxygen? a. question 14 18. Which reaction sequence from the above questions involves the Kolbe synthesis? a. question 14 19. Which reaction sequence from the above questions involves a nucleophilic aromatic substitution mechanism? a. question 14 20. Which reaction sequence from the above questions involves a benzyne intermediate? a. question 14 b. question 15 c. question 16 d. not a.-c. b. question 15 c. question 16 d. not a.-c. b. question 15 c. question 16 d. not a.-c. b question 15 c. question 16 d. not a.-c.

Explanation / Answer

17) Question 16

18) Question 15

19) Not a-c

20) Question 14

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