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Concept explainers
Interpretation:
The given compounds are to be synthesized from benzene.
Concept introduction:
Electrophilic substitution reaction in
The mechanism of electrophilic aromatic substitution involves the attack of electrophile, followed by the removal of hydrogen ions.
Benzene and substituted benzene undergo electrophilic substitution reactions in the presence of an electrophilic reagent. The electrophilic substitution on the substituted benzene occurs on the basis of the nature of the substituent present on the benzene ring. If the group is ortho-para directing, then ortho and para isomers will be formed as the product and if the group is meta directing, a meta product is formed.
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Chapter 15 Solutions
ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
- Starting with toluene, outline a synthesis of each of the following: (a) o-nitrobenzoic acid (b) m-nitrobenzoic acid (c) 3-chlorobenzoic acid (d) p-bromobenzoic acidarrow_forwardStarting with 2-methylpropene, outline a synthesis of (a) (CH3)3COH (b) (CH3)2C(OH)CH2Brarrow_forward(a) benzene can potentially react with Lewis acid to form new carbon-carbon bond. Propose the starting material and stepwise mechanism to produce new chemical structure which consists of a formula molecule of C11H16.arrow_forward
- Write the structure of the major organic product formed in the reaction of 1-pentene with each of the following: (a) Hydrogen chloride (b) Dilute sulfuric acid (c) Diborane in diglyme, followed by basic hydrogen peroxide (d) Bromine in carbon tetrachloride (e) Bromine in water (f) Peroxyacetic acid (g) Ozone (h) Product of part (g) treated with zinc and water (i) Product of part (g) treated with dimethyl sulfide (CH3)2Sarrow_forwardPredict the mononitration products of the following aromatic compounds.(a) p-methylanisole (b) m-nitrochlorobenzene(c) p-chlorophenol (d) m-nitroanisolearrow_forward(a) How will you carry out the following conversions?(i) Acetylene to Acetic acid (ii) Toluene to m-nitrobenzoic acid(iii) Ethanol to Acetone(b) Give reasons :(i) Chloroacetic acid is stronger than acetic acid.(ii) pH of reaction should be carefully controlled while preparing ammonia derivatives of carbonyl compounds.arrow_forward
- (a) The Friedel-Crafts reaction of benzene with 2-chloro-3-methylbutane in the presence of AlCl3 occurs with a carbocation rearrangement. Give mechanistic explanation and the product formed. (b) Predict the product(s) will be formed from the following reactions: (i) Bromination of p-methylbenzoic acid (ii) Sulphonation of m-bromoanisole (iii) Friedel-craft acylation of o-bromonitrobenzenearrow_forward(a) Describe the following giving chemical equations :(i) De-carboxylation reaction (ii) Friedel-Crafts reaction(b) How will you bring about the following conversions?(i) Benzoic acid to Benzaldehyde (ii) Benzene to m-Nitroacetophenone (iii) Ethanol to 3-Hydroxybutanalarrow_forward(a) How will you convert:(i) Benzene to acetophenone (ii) Propanone to 2-Methylpropan-2-ol(b) Give reasons :(i) Electrophilic substitution in benzoic acid takes place at meta position.(ii) Carboxylic acids are higher boiling liquids than aldehydes, ketones and alcohols of comparable molecular masses.(iii) Propanal is more reactive than propanone in nucleophilic addition reactions.arrow_forward
- (a) Draw the structures of the following compounds :(i) 4-Chloropentan-2-one (ii) p-Nitropropiophenone(b) Give tests to distinguish between the following pairs of compounds :(i) Ethanal and Propanal (ii) Phenol and Benzoic acid(iii) Benzaldehyde and Acetophenonearrow_forwardShow how you would synthesize the following compounds, starting with benzene or toluene and any necessary acyclic reagents. Assume para is the major product (and separable from ortho) in ortho, para mixtures. (a) 3-nitro-4-bromobenzoic acid (b) 3-nitro-5-bromobenzoic acid (c) 4-butylphenol (d) 2-(4-methylphenyl)butan-2-olarrow_forwardUsing cyclooctyne as your starting material, show how you would synthesize the following compounds. (Once you haveshown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)(a) cis-cyclooctene (b) cyclooctane (c) trans-1,2-dibromocyclooctane(d) cyclooctanone (e) 1,1-dibromocyclooctane (f) 3-bromocyclooctene(g) cyclooctane-1,2-dionearrow_forward
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