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
- Give reasons for the following: (i) p-nitrophenol is more acidic than p-methylphenol. (ii) Bond length of C—O bond in phenol is shorter than that in methanol. (iii) (CH3)3C—Br on reaction with sodium methoxide (Na+ _OCH3) gives alkene as the main product and not an ether.arrow_forwardFollowing is the structural formula of the tranquilizer meparfynol (Oblivon). Propose a synthesis for this compound starting with acetylene and a ketone. (Notice the -yn- and -ol in the chemical name of this compound, indicating that it contains alkyne and hydroxyl functional groups.)arrow_forwardDraw structural formulas for these ketones. (a) Ethyl isopropyl ketone (b) 2-Chlorocyclohexanone (c) 2,4-Dimethyl-3-pentanone (d) Diisopropyl ketone (e) Acetone (f) 2,5-Dimethylcyclohexanonearrow_forward
- A postgraduate student wanted to synthesized two carbonyl compounds known as compounds M and N using oxidation of alcohol. However, these carbonyl compounds should have more than 6 carbon atoms. Draw two (2) possible structural formulae for compounds M and N. How would you distinguish between compounds M and N?arrow_forward(a) Give chemical tests to distinguish between the following pairs of compounds :(i) Ethanal and Propanal (ii) Phenol and Benzoic acid(b) How will you bring about the following conversions?(i) Benzoic acid to benzaldehyde (ii) Ethanal to but-2-enal (iii) Propanone to propeneGive complete reaction in each case.arrow_forwardPropose structures for molecules that fit the following descriptions:(a) An aldehyde with the formula C5H10O(b) An ester with the formula C6H12O2(c) A compound with the formula C3H7NOS that is both anamide and a thiolarrow_forward
- 11) Synthesize 2-methyl-3-hydroxycyclohexone from cyclohexone, methyl iodide, and inorganic precursors.arrow_forwardWrite down the reaction of acetaldehyde with the following.(b) 2,4-dinitrophenylhydrazine (c) I2 / NaOHarrow_forwardWhat reactions and reagents can be used to make phenol from benzene if electrophilic aromatic substitution reactions are excluded and benzene is the only source of carbon?arrow_forward
- Draw the structural formulas of the following compounds:(a) 2,3-Dimethylpentanal(b) 1,3-Dibromopropanone(c) 4-hydroxy-4-methylhexan-2-onearrow_forwardDraw the structure of the following compounds which parent names have been traced to a common name; (a)5-methyl-4-nitroimidazole (b)2-chloro-4-methoxythiazole.arrow_forwardGive the chemical tests to distinguish between following pair of compounds : (i) Propanol and propanone (ii) Ethyl acetate and methyl acetate (iii) Benzaldehyde and benzoic acid (iv) Benzaldehyde and acetaldehyde (v) Formic acid and acetic acid (vi) Propanal and propanol (vii) Ethanoic acid and ethylethanoatearrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning