Interpretation:
Aniline is to be converted into the given desired product mentioned in each part.
Concept introduction:
Electrophiles are electron deficient species that have positive or partially positive charge. Lewis acids are electrophiles that accept electron pair.
Nucleophiles are electron rich species that have negative or partially negative charge. Lewis bases are nucleophiles that donate electron pair.
Free radical is an atom, molecule, or ion that has an unpaired electron, which makes it highly chemically reactive.
Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.
Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.
Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.
Aniline is a primary
Aniline and substituted aniline reacts with nitrous acid at low temperature to form benzene diazonium salts.
The reduction of nitro group results in the formation of primary amine.
When aniline reacts with acetic anhydride, the product formed after the reaction is acetanilide.
When aniline reacts with Phthalimide
On nitration of acetanilide in the presence
When acetanilide reacts with chloro sulfuric acid, it forms p-acetamido benzene sulfonyl chloride.
Further, when p-acetamido benzene sulfonyl chloride reacts with ammonia, it gives rise to p-acetamido benzene sulfonamide, which on alkaline hydrolysis gives sulfanilamide.
When an aniline reacts with two moles of methyl iodide in the presence of a base, it forms N, N-dimethylaniline.
When an aniline reacts with nitrous acid at
When benzenediazonium halide reacts with copper(I) chloride, it forms chlorobenzene.
When benzenediazonium halide reacts with copper (I) bromide, it forms bromobenzene.
When benzenediazonium halide reacts with potassium iodide, it forms iodobenzene.
When benzenediazonium halide reacts with copper (I) cyanide, it forms benzonitrile.
Alkaline hydrolysis of benzonitrile results in the formation of benzoic acid.
When benzenediazonium halide reacts with copper oxide, it forms phenol.
When benzenediazonium halide reacts with Hypo phosphorous acid in the presence of moisture, it forms benzene.
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Chapter 20 Solutions
EBK ORGANIC CHEMISTRY
- Verapamil, a coronary artery vasodilator, is used in the treatment of angina caused by insufficient blood flow to cardiac muscle. Even though its effect on coronary vasculature tone was recognized over 30 years ago, only recently has its role as a calcium channel blocker become understood. Following is a retrosynthetic analysis leading to a convergent synthesis; it is convergent because (A) and (B) are made separately and then combined (i.e., the route converges) to give the final product. Convergent syntheses are generally much more efficient than those in which the skeleton is built up stepwise. Q. Two steps are required to convert (D) to (C). The first is treatment of (D) with ethyl chloroformate. What is the product of this first step? What reagent can be used to convert this product to (C)?arrow_forwardVerapamil, a coronary artery vasodilator, is used in the treatment of angina caused by insufficient blood flow to cardiac muscle. Even though its effect on coronary vasculature tone was recognized over 30 years ago, only recently has its role as a calcium channel blocker become understood. Following is a retrosynthetic analysis leading to a convergent synthesis; it is convergent because (A) and (B) are made separately and then combined (i.e., the route converges) to give the final product. Convergent syntheses are generally much more efficient than those in which the skeleton is built up stepwise. Q. How do you account for the regioselectivity of the nucleophilic displacement involved in converting (C) to (B)?arrow_forwardThe saccharide shown here is present in some plant-derived foods. (a) Indicate the anomeric carbon atom(s) in this structure by drawing a circle around the atom(s) or by drawing an arrow pointing to the atom(s). (b) Would this saccharide give a positive result with Benedict’s reagent? Why or why not? (c) Would this saccharide give a positive result with Barfoed’s reagent? Why or why not? (d) Would this saccharide give a positive result with Seliwanoff’s reagent? Why or why not? (e) In a separate set of experiments, the saccharide solution was treated with a reagent that breaks glycosidic bonds. After this treatment, would any of the three assays give different results? Be sure to indicate which assay results would be different and give a reason.arrow_forward
- Rank the compounds in each of the following groups in order of their reactivity to electrophilic substitution: (a) Nitrobenzene, phenol, toluene, benzene (b) Phenol, benzene, chlorobenzene, benzoic acid (c) Benzene, bromobenzene, benzaldehyde, anilinearrow_forwardNifedipine (Procardia and Adalat) belongs to a class of drugs called calcium channel blockers and is effective in the treatment of various types of angina, including that in- duced by exercise. Show how nifedipine can be synthesized from 2-nitrobenzaldehyde, methyl acetoacetate, and ammonia. (Hint: Review the chemistry of your answers to Problems 19.43 and 19.54 and then combine that chemistry to solve this problem.) NO COOME MEOOC, acid + 2 `NO2 OMe +NH3 СНО H Nifedipinearrow_forwardIn the mid-1930s a substance was isolated from a fungus that is a parasite of ryes and other grasses. This alkaloid, lysergic acid, has been of great interest to chemists because of its strange, dramatic action on the human mind. Many derivatives of lysergic acid are known, some with medicinal applications. Perhaps the best known derivative of lysergic acid is the potent hallucinogen lysergic acid diethylamide (LSD): మగవా జి N-H LSD (CH25N;O) Like other alkaloids, LSD is a weak base, with Kp = 7.6 × 107. What is the pH of a 0.94 M solution of LSD? pH =arrow_forward
- (d) When a primary amine is combined with a ketone, both an imine and an enamine can be obtained. With most ketones, the major product is the imine, as shown: H3C NH2 -N -CH3 -CH3 imine: major product enamine: minor product However, in some cases, like the one shown below, the major product is the enamine. CO₂Et CO₂Et CO₂Et H H3C NH2 -CH3 imine: minor product -CH3 enamine: major product Referring to specific features of the starting materials, intermediates, or products, explain why.arrow_forwarda) Write a mechanism for the formation of semicarbazone Y.b) Explain why formation of imine Z is not favoured.arrow_forwardHow do you account for the fact that N-phenylacetamide (acetanilide) is less reactive toward electrophilic aromatic substitution than is aniline? -NHCCH, -NH, N-Phenylacetamide (Acetanilide) Anilinearrow_forward
- B) Rank the following compounds toward increasing acidity, why? 2) 1,3-benzoqounoin 2)cyclohexanoic acid 3)cyclohexanal 4) cyclohexanolarrow_forwardEach of the following is a set of directions for carrying out a reaction or sequence of reactions. Rewrite each set ofdirections in the form of a synthesis.(a) To 2-ethylcyclohexanone, add lithium diisopropylamide, and when that reaction is complete, add bromoethane toyield 2,6-diethylcyclohexanone.(b) Add molecular bromine to 2,2-dimethylcyclohexanone in the presence of acetic acid to yield 6-bromo-2,2-dimethylcyclohexanone. To the resulting mixture, add sodium cyanide to yield 6-cyano-2,2-dimethyl-cyclohexanone.(c) Treat pent-4-ynoic acid with diazomethane to produce methyl pent-4-ynoate. Next, add sodium hydride, followed by(bromomethyl)benzene, to yield methyl 6-phenylhex-4-ynoate.arrow_forward(a)Which compound/s will produce an orange precipitate upon reaction with 2,4-DNPH? (b)Which compound/s will test positive towards Baeyer’s test? (c)Which compound/s will produce a brick-red precipitate upon reaction with Fehling’s reagent (CuSO4, tartrate, NaOH)? (d)Which compound/s will test positive towards the Iodoform test?arrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning