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Concept explainers
Interpretation:
Using aniline as a starting material and 2-aminothiazole, the synthesis of sulfathiazole is to be shown and the conversion of sulfathiazole to succinylsulfathiazole is to be provided.
Concept Introduction:
▸ Electrophiles are electron deficient species which has positive or partially positive charge. Lewis acids are electrophiles which accept electron pair.
▸ Nucleophiles are electron rich species which has negative or partially negative charge. Lewis bases are nucleophiles which 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
▸ 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 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
▸ Electrophiles are electron deficient species which has positive or partially positive charge. Lewis acids are electrophiles which accept electron pair.
▸ Carboxamide undergoes hydrolysis more rapidly than sulfonamide.
▸ The aniline undergoes acetylation to protect the amino group and form acetanilide.
▸ Acetanilide undergoes the electrophilic
▸ Addition of
▸ The sulfathiazole reacts with the succinic anhydride which leads to the formation of final product that is succinylsulfathiazole.
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Chapter 20 Solutions
Organic Chemistry, 12e Study Guide/Student Solutions Manual
- Draw a structural formula for each amine and amine derivative. (a) N,N-Dimethylaniline (b) Triethylamine (c) tert-Butylamine (d) 1,4-Benzenediamine (e) 4-Aminobutanoic acid (f) (R)-2-Butanamine (g) Benzylamine (h) trans-2-Aminocyclohexanol (i) 1-Phenyl-2-propanamine (amphetamine) (j) Lithium diisopropylamide (LDA) (k) Benzyltrimethylammonium hydroxide (Triton B)arrow_forwardShow how to synthesize the following amines from the indicated starting materials.(a) N-cyclopentylaniline from anilinearrow_forwardArrange the members of each group in order of decreasing basicity: (a) Ammonia, aniline, methylamine (b) Acetanilide, aniline, N-methylaniline (c) 2,4-Dichloroaniline, 2,4-dimethylaniline, 2,4-dinitroaniline (d) 3,4-Dichloroaniline, 4-chloro-2-nitroaniline, 4-chloro-3-nitroaniline (e) Dimethylamine, diphenylamine, N-methylanilinearrow_forward
- Show how to synthesize the following amines from the indicated starting materials byacylation–reduction.(a) N-butylpiperidine from piperidinearrow_forwardShow how to prepare the following aromatic amines by aromatic nitration, followed by reduction. You may use benzene andtoluene as your aromatic starting materials.(a) anilinarrow_forwardGive reasons :(a) Aniline is a weaker base than cyclohexyl amine.(b) It is difficult to prepare pure amines by ammonolysis of alkyl halides.arrow_forward
- Show how you would use appropriate acyl chlorides and amines to synthesize thefollowing amides.(a) N,N-dimethylacetamide (b) acetanilide (PhNHCOCH3)(c) cyclohexanecarboxamide (d)arrow_forward(D)The best route to synthesise aromatic primary amines is by reduction of the corresponding nitro compounds. Draw the reaction scheme for the preparation of p-toluidine.arrow_forwardShow how you might utilize the reduction of an amide, oxime, or a nitrile to carry out each of the following transformations (a)Benzoic acid to N-ethyl-N-benzylamine (b)1-Bromopentane to hexylamine (c)Propanoic acid to tripropylamine (d)2-Butanone to sec-butylaminearrow_forward
- Draw the structure of each compound.(a) o-nitroanisole (b) 2,4-dimethoxyphenol (c) p-aminobenzoic acid(d) 4-nitroaniline (e) m-chlorotoluene (f) p-divinylbenzene(g) p-bromostyrene (h) 3,5-dimethoxybenzaldehyde (i) tropylium chloride(j) sodium cyclopentadienide (k) 2-phenylpropan-1-ol (l) benzyl methyl ether(m) p-toluenesulfonic acid (n) o-xylene (o) 3-benzylpyridinarrow_forwardAlthough acetanilide and phenacetin are not appreciably acidic, aceta- minophen (like aspirin) is a stronger acid than water. What problem would you encounter if the unknown component were acetaminophen rather than acetanilide or phenacetin, and you extracted the aspirin with 5% NaOH? Explain, giving equations for any relevant reactions.arrow_forwardThe two most general amine syntheses are the reductive amination of carbonyl compounds and the reduction of amides.Show how these techniques can be used to accomplish the following syntheses.(a) benzoic acid S benzylamine (b) benzaldehyde S benzylamine(c) pyrrolidine S N@ethylpyrrolidine (d) cyclohexanone S N@cyclohexylpyrrolidine(e) HOOC¬(CH2)3 ¬COOH S pentane@1,5@diamine (cadaverine)arrow_forward
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