(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, Loose-leaf Version
- (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_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_forward(a) What product would you expect from cleavage of tetrahydrofuran with HI? (b) Outline a mechanism for the reaction.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_forward
- (a) Account for the following :(i) Propanal is more reactive than propanone towards nucleophilic reagents.(ii) Electrophilic substitution in benzoic acid takes place at meta position.(iii) Carboxylic acids do not give characteristic reactions of carbonyl group.(b) Give simple chemical test to distinguish between the following pairs of compounds:(i) Acetophenone and benzaldehyde(ii) Benzoic acid and ethylbenzoate.arrow_forwardGive the structure of the product formed on reaction of ethyl acetoacetate with each of the following: (a) 1-Bromopentane and sodium ethoxide (b) Saponification (basic hydrolysis) and decarboxylation of the product in part (a) (c) Methyl iodide and the product in part (a) treated with sodium ethoxide (d) Saponification and decarboxylation of the product in part (c) (e) 1-Bromo-3-chloropropane and one equivalent of sodium ethoxide (f) Product in part (e) treated with a second equivalent of sodium ethoxide (g) Saponification and decarboxylation of the product in part (f) (h) Phenyl vinyl ketone and sodium ethoxide (i) Saponification and decarboxylation of the product in part (h)arrow_forwardWhen phenyl 3,4-dimethylbenzoate undergoes electrophilic aromatic substitution, one ring reacts much more readily than the other. (a) Which one is it? Encircle the ring (b) Explain your answer. (c) Draw the resulting product/s when it undergoes bromination reaction. Product (c) (a) Explanation (b)arrow_forward
- Quinapril (trade name Accupril) is used to treat high blood pressure and congestive heart failure. One step in the synthesis of quinapril involves reaction of the racemic alkyl bromide A with a single enantiomer of the amino ester B. (a) What two products are formed in this reaction? (b) Given the structure of quinapril, which one of these two products is needed tosynthesize the drug?arrow_forward(c) The sedative, R-thalidomide, was once used to address symptoms of morning sickness in expectant mothers, however, when it was discovered that S- thalidomide causes deformities in infants, the use of R-thalidomide as a sedative was discontinued. With the help of a reaction mechanism, explain why enantiopure R-thalidomide can not be safely used as a sedative without affecting infantsarrow_forwardQuinapril (trade name Accupril) is used to treat high blood pressure and congestive heart failure. One step in the synthesis of quinapril involves reaction of the racemic alkyl bromide A with a single enantiomer of the amino ester B. (a) What two products are formed in this reaction? (b) Given the structure of quinapril, which one of these two products is needed to synthesize the drug?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning