Assignment_5_Reactions_of_aromatic_compounds_Answers

Assignment_5_Reactions_of_aromatic_compounds_Answers - CHM...

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CHM 2120 – Assignment 5 – Reactions of aromatic compounds ANSWERS In this assignment: - Electrophilic aromatic substitution - Manipulation of products of aromatic substitution - Acidity/basicity is affected by aromaticity and substituents on aromatic rings - Synthesis of benzene derivatives 1. Show how you would synthesize each of the following monosubsituted benzenes: a. Nitrobenzene HNO 3 H 2 SO 4 NO 2 b. Chlorobenzene Cl 2 FeCl 3 Cl c. Methylbenzene (toluene) MeCl AlCl 3 CH 3 d. Isopropylbenzene (2 ways) n -PrCl OR i -PrCl AlCl 3 e. Acetylbenzene (acetophenone) AlCl 3 O Cl O
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ANSWERS - Assignment 5 – Reactions of aromatic compounds 2 2. Give the product expected or reagents required for each of the following reactions. Clearly justify the formation of the major product. Note: you could be asked on the test to support your answer with a mechanism and any relevant resonance structures as shown in class. O Br 2 FeBr 3 a) b) c) d) e) f) NO 2 Br 2 FeBr 3 Br HNO 3 H 2 SO 4 Cl O AlCl 3 CH 2 Cl 2 (inert solvent) H 2 Pd/C Br O O Br Br OMe is an o,p -director NO 2 Br NO 2 is a m -director Br Br O 2 N O i-Pr is an o,p -director but sterics hinder the formation of the o -substituted product NBS ROOR heat just like an allylic bromination, but this is a benzylic bromination instead Br is an o,p -director (eventhoughi t 'sa deactivating group)
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ANSWERS - Assignment 5 – Reactions of aromatic compounds 3 3. Give the major product(s) that would be obtained when each of the following compounds is subjected to Br 2 and FeBr 3 : a. Ethylbenzene b. Anisole c. Fluorobenzene d. Benzoic acid e. Nitrobenzene Br Br O Br O Br F Br F Br CO 2 H Br NO 2 Br
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ANSWERS - Assignment 5 – Reactions of aromatic compounds 4 4. When benzene is reacted with 1-chloropropane and aluminum trichloride, a mixture of n-propylbenzene and isopropylbenzene is obtained. Explain by drawing the mechanism for the reaction. Cl AlCl 3 major Cl AlCl 3 H 3 C Cl AlCl 3 H H H H :B B=C l - H minor H 3 C C H 2 H H +C l-A lC l 3 C H CH 3 CH 3 H H fast rearrangement B: C H CH 3 CH 3 H major slower intermolecular reaction 5. Draw a mechanism for the following transformation: OH CH 3 SO 3 H H + O H H H H B: B= -
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Assignment_5_Reactions_of_aromatic_compounds_Answers - CHM...

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