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 W/OWL
- The number of 2sp^2 hybridized atoms in is: A. 8; B. 6; C.4; D.2; E.0;arrow_forwardThe highest boiling compound from among the following isA. 2-methylheptane; B. 3-methylheptane; C. 2,2-dimethylhexane;D. octane; E. 2,2,3-trimethylpentanearrow_forwardWhich of the following features are found in the most stable structure ofCH5NO that does not have a CO bond?w. a π bond, x. two NH bonds, y. one OH bond, z. 3 lone pairsA. w, x; B. x, y; C. y, z; D. x, y, z; E. all of them.arrow_forward
- Which one of the following functional groups is not present in thecompound shownA. amine; B. aldehyde, C. ether; D. amide. E. ketonearrow_forwardWhich of the following formulas correspond to at least one compound inwhich resonance is important?w. C2H5N x. C3H5Br; y. C3H4; z. C4H6.A. w, x, y; B. x, y, z; C. w, x, z; D. w, y, z; E. all of themarrow_forwardPredict the product(s) that are formed after each step for reactions 1-4. In each case, consider formation of any chiral center(s) and draw all expected stereoisomers. 1) OH 1) HBr (SN2) 2) NaOH, heat 3) BH3, THF 4) H2O2, NaOH 2) OH 1) SOCI 2, py 2) NaOEt 3) Br2, H₂O 3) OH 1) H2SO4 conc. 2) HBr, ROOR 3) KOtBu 4) OH 1) TsCl, py 2) NaOEt 3) 03 4) DMSarrow_forward
- Which of the following rings has the least strain in its most stableconformation?A. Cyclobutane; B. Cyclopentane; C. Cyclohexane; D. Cycloheptane;E. Cyclooctanearrow_forwardThe number of different carbon skeletons that have a main chain of 9carbons and an ethyl branch isA 3; B. 4; C. 5; D. 6; E. 7arrow_forwardQ5: Classify the following pair of molecules as constitutional isomers, enantiomers, diastereomers, the same molecule, or completely different molecules. Br O CI Br OH OH 111 Br .!!!/Br F OH and ...m Br Br OH CI Br OH ་་་་་" ། ་arrow_forward
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