Concept explainers
a)
Interpretation:
Starting from benzene as the only source of
Concept introduction:
In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the keto group is a meta directing group. Hence to prepare p-chloroacetophenone, benzene has to be halogenated and the halobenzene obtained should be subjected to Friedal-Crafts acylation.
To state:
Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how p-chloroacetophenone can be synthesized.
b)
Interpretation:
Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m-bromonitrobenzene can be synthesized is to be stated.
Concept introduction:
In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the nitro group is a meta directing group. Hence to prepare m-bromonitrobenzene, benzene has to be first nitrated and the nitrobenzene obtained should be halogenated.
To state:
Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m–bromonitrobenzene can be synthesized.
c)
Interpretation:
Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how o-bromobenzenesulfonic acid can be synthesized is to be stated.
Concept introduction:
In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the sulfonic acid group is a meta directing group. Hence to prepare o-bromobenzenesulfonic acid, benzene has to be halogenated and the halobenzene obtained should be subjected to sulfonation.
To state:
Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how o-bromobenzenesulfonic acid can be synthesized.
d)
Interpretation:
Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m-chlorobenzenesulfonic acid can be synthesized is to be stated.
Concept introduction:
In aromatic electrophilic substitution reactions halogens are ortho and para directing groups while the sulfonic acid group is a meta directing group. Hence to prepare m-chlorobenzenesulfonic acid, benzene has to be sulfonated and the benzenesulfonicacid obtained should be halogenated.
To state:
Starting from benzene as the only source of aromatic compounds and assuming that the ortho and para isomers can be separated, if necessary, how m-chlorobenzenesulfonic acid can be synthesized.
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Chapter 16 Solutions
ORGANIC CHEMISTRY W/OWL
- B 1 of 2 Additional problems in preparation to Midterm #1: 1.) How can the following compounds be prepared using Diels-Alder reaction: CH3 O CN (a) (b) CN CH3 2.) What is the missing reagent in the shown reaction? H3C + ? H3C H3C CN H3C ''CN (၁) H 3.) Write the products 1,2-addition and 1,4-addition of DBr to 1,3-cyclohexadiene. Remember, D is deuterium, a heavy isotope of hydrogen. It reacts exactly like hydrogen. 4.) In the shown reaction, which will be the kinetic product and which will be the thermodynamic product? H3C CI H3C HCI H3C + 5.) Which of the following molecules is aromatic? (a) (b) (c) H 6.) Which of the following molecules is aromatic? (a) (b) (c) 7.) Write the mechanism for the shown reaction. + Ха AICI 3 CI 8.) Suggest reagents that would convert benzene into the shown compounds. CI NO2 -8-6-6-8-a (a) (b) (c) (d) (e) (a) SO3H Brarrow_forwardThe 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_forward
- Which 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_forwardWhich 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_forward
- Predict 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_forwardWhich 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_forward
- Q5: 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_forwardConsidering only rotation around the 1-2 bond, how many differentstaggered conformations are there of 1,2-dibromo-1,2-dichloropropane?A: 2; B. 3; C. 4; D. 6; E. more than 6.arrow_forwardcan you help me solve thisarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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