(a)
Interpretation:
Similarities between the mechanism of deamination of
Concept Introduction:
Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.
Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal
Step 1: Add proton (protonation of Pinacol using acid catalyst).
Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).
Step 3: 1, 2-shift (migration of substituent from
Step 4: deprotonation occurs (take a proton away).
(b)
Interpretation:
Reason for the expansion of ring in the deamination of
Concept Introduction:
Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.
Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that
Step 1: Add proton (protonation of Pinacol using acid catalyst).
Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).
Step 3: 1, 2-shift (migration of substituent from
Step 4: deprotonation occurs (take a proton away).
(b)
Interpretation:
Concept Introduction:
Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.
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Chapter 23 Solutions
Organic Chemistry
- Each of the following reactions has been carried out under conditions such that disubstitution or trisubstitution occurred. Identify the principal organic product in each case. (a) Nitration of p-chlorobenzoic acid (dinitration) (b) Bromination of aniline (tribromination) (c) Bromination of o-aminoacetophenone (dibromination) (d) Bromination of p-nitrophenol (dibromination) (e) Reaction of biphenyl with tert-butyl chloride and iron(III) chloride (dialkylation) (f) Sulfonation of phenol (disulfonation)arrow_forwardAddition of one equivalent of ammonia to 1-bromoheptane gives a mixture of heptan-1-amine,some dialkylamine, some trialkylamine, and even some tetraalkylammonium bromide.(a) Give a mechanism to show how this reaction takes place, as far as the dialkylamine.(b) How would you modify the procedure to get an acceptable yield of heptan-1-amine?arrow_forward(a) Account for the following :(i) CH3CHO is more reactive than CH3COCH3 towards reaction with HCN.(ii) Carboxylic acid is a stronger acid than phenol.(b) Write the chemical equations to illustrate the following name reactions:(i) Wolff-Kishner reduction (ii) Aldol condensation (iii) Cannizzaro reactionarrow_forward
- (a) Give a plausible explanation for each one of the following :(i) There are two – NH2 groups in semicarbazide. However, only one such group is involved in the formation of semicarbazones.(ii) Cyclohexanone forms cyanohydrin in good yield but 2, 4, 6-trimethylcyclohexanone does not.(b) An organic compound with molecular formula C9H10O forms 2, 4, – DNP derivative, reduces Tollens’ reagent and undergoes Cannizzaro’s reaction. On vigorous oxidation it gives 1, 2-benzene-di- carboxylic acid. Identify the compound.arrow_forward(a) Explain the mechanism of a nucleophilic attack on the carbonyl group of an aldehyde or a ketone.(b) An organic compound (A) (molecular formula CgH16Q2) was hydrolysed with dilute sulphuric acid to give a carboxylic acid (B) and an alcohol (C). Oxidation of (C) with chromic acid also produced (B). On dehydration (C) gives but-1-ene. Write the equations for the reactions involved.arrow_forwardWhen N-bromosuccinimide is added to hex-1-ene in CCl4 and a sunlamp is shone on themixture, three products result.(a) Give the structures of these three products.(b) Propose a mechanism that accounts for the formation of these three productsarrow_forward
- From the given structures which is(a) an acid halide? (b) a secondary amide (c) an aldehyde incapable of self-aldol consensation?arrow_forward(iii) Rank the carbonyl compounds given below in terms of their relative reactivity with sodium borohydride. RT R CH3 CI (iv) Suggest two factors which combine to make the aldehyde react with sodium borohydride at a different rate from the ketone. (v) Based on electronegativity one might assume that the ester and acid chloride possess similar reactivity towards nucleophiles. Suggest why this turns out not to be the case (your answer should mention resonance and inductive effects).arrow_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) p-aminobenzoic acid (b) 2-methyl-1-phenylbutan-2-ol (c) 5-chloro-2-methylanilinearrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning