
a)
Interpretation:
Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2-bromo-4-nitrotoluene can be synthesized is to be stated.
Concept introduction:
In
Electrophilic substitution of di and trisubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.
To state:
Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2-bromo-4-nitrotoluene can be synthesized.
b)
Interpretation:
Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 1,3,5-trinitrobenzene can be synthesized is to be stated.
Concept introduction:
In aromatic electrophilic substitution reactions the nitro group is a meta directing group. Nitration of benzene gives nitrobenzene. Further nitration of nitrobenzene will introduce nitro groups into the two meta positions to yield the trinitro compound.
To state:
Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 1,3,5-trinitrobenzene can be synthesized.
c)
Interpretation:
Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2,4,6-tribromoaniline can be synthesized is to be stated.
Concept introduction:
In aromatic electrophilic substitution reactions, the amino group is an ortho and para directing group. Nitration of benzene gives nitrobenzene. Nitrobenzene can be reduced to aminobenzene (aniline). Aniline upon bromoination will yield 2,4,6-tribromoaniline.
To state:
Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how 2,4,6-tribromoaniline can be synthesized.
d)
Interpretation:
Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how m-fluorobenzoic acid can be synthesized is to be stated.
Concept introduction:
In aromatic electrophilic substitution reactions the
To state:
Starting from benzene or toluene and assuming that the ortho and para isomers can be separated, how m-fluorobenzoic acid can be synthesized.

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Chapter 16 Solutions
Organic Chemistry - With Access (Custom)
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- A mixture of C7H12O2, C9H9OCl, biphenyl and acetone was put together in a gas chromatography tube. Please decide from the GC resutls which correspond to the peak for C7,C9 and biphenyl and explain the reasoning based on GC results. Eliminate unnecessary peaks from Gas Chromatography results.arrow_forwardIs the molecule chiral, meso, or achiral? CI .CH3 H₂C CIarrow_forwardPLEASE HELP ! URGENT!arrow_forward
- Identify priority of the substituents: CH3arrow_forwardHow many chiral carbons are in the molecule? OH F CI Brarrow_forwardA mixture of three compounds Phen-A, Acet-B and Rin-C was analyzed using TLC with 1:9 ethanol: hexane as the mobile phase. The TLC plate showed three spots of R, 0.1 and 0.2 and 0.3. Which of the three compounds (Phen-A; Acet-B or Rin-C) would have the highest (Blank 1), middle (Blank 2) and lowest (Blank 3) spot respectively? 0 CH: 0 CH, 0 H.C OH H.CN OH Acet-B Rin-C phen-A A A <arrow_forward
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