Question

The synthesis of tyramine from benzene can be accomplished via the following synthetic route: Steps: 5, 6, 7

The synthesis of tyramine from benzene can be accomplished via the following synthetic route: Enter your answer as a series of letters without punctuation (i.e. 'bgh'). Select reagents from the table to show how you would perform steps 5, 6, and 7. Reagents a. CH_3 CI, AICI_3 b. CH_3 COCl, AICl_3 C. HNO_3, H_2SO_4 d. HNO_2, H_2 SO_4 e. Cu_2O, H_2O, Cu (NO_3) _2 f. NBS g. NaCN h. H_2, Pt i. LiAIH_4 then H_2O j. (CH_3CO)_2O k. H_3O I. NH_3 then NaBH_3CN

Answer 1

1) a) CH3Cl, AlCl3

2) c) HNO3, H2SO4

3) h) H2, Pt

4) d) HNO2, H2SO4

5) k) H3O+

6) f) NBS

7) g) NaCN

8) i) LiAlH4, H2O

Explanation: Reaction of benzene with CH3Cl, AlCl3 produces alkyl benzene as product. -CH3 group on benzene ring is an electron donating group which directs the incoming electrophile to ortho or para position. reduction of -NO2 group with H2, Pt produces -NH2 group. diazotisation of aniline with HNO2, H2SO4 produces diazonium cation as an intermediate. Hydrolysis of diazonium cation produces phenol as product. NBS is a brominating agent which gives bromination at benzylic position. substitution reaction of alkyl halide with NaCN produces cyanide as product. reduction of -CN group with LiAlH4 produces amine as product.