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(a)
Interpretation:
A curved-arrow mechanism corresponding to the hydroxide-catalyzed hydration of acetaldehyde is to be stated.
Concept introduction:
The
(b)
Interpretation:
A curved-arrow mechanism corresponding to the decomposition of acetone cyanohydrin in aqueous hydroxide is to be stated. The reason as to why the
Concept introduction:
A chemical reaction in which a reactant breaks down to generate at least two products is known as decomposition reaction. The involvement of an energy source like heat also takes place in decomposition reaction.
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Chapter 19 Solutions
EBK ORGANIC CHEMISTRY
- Write chemical equations expressing each of the following: (a) Preparation of o-nitrophenyl acetate by sulfuric acid catalysis of the reaction between a phenol and an acid anhydride. (b) Esterification of 2-naphthol with acetic anhydride in aqueous sodium hydroxide (c) Reaction of phenol with benzoyl chloridearrow_forward(a) Explain why an alkylamine is more basic than ammonia?(b) How would you convert(i) Aniline to nitrobenzene (ii) Aniline to iodobenzenearrow_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 tosynthesize the drug?arrow_forward
- 24.82 When the compound shown here is heated, ethene gas is evolved and a product with the formula C14H3O2 is formed. The 'H NMR and 13C NMR spectra of C14H8O2 are shown below. (There are two signals >150 ppm in the 13C NMR spectrum. Recall that the 13C NMR signal at 77 ppm is from the CDCI3 solvent.) (a) Draw the structure of C,14H3O2. (b) Draw the mechanism that accounts for its formation. (c) What is the main driving force that favors the products of this reaction? ? C14H3O2 C14H8O2 9. 8 7 6 4 3 2 1 250 200 150 100 50 Chemical shift (ppm) Chemical shift (ppm)arrow_forward18.18 Provide a structural formula for the product from each of the following reactions. (a) (c) (e (1) LDA (2) CH,CH,I NaH CI (b) (d) O. (f Br, CH,CO,H Br, (excess), NaOHarrow_forwardGive reasons: (i) Bond length of C = O in carboxylic acids is slightly larger than C = O bond length in carbonyl compounds. (ii) There are two –NH2 groups in semicarbazide. However, only one –NH2 group is involved in the formation of semicarbazones. (iii) Benzoic acid is less soluble in water than acetic acid. (iv) Formic acid is a stronger acid than acetic acid.arrow_forward
- (a) Why are alkyl halides insoluble in water? (b) Why is Butan-l-ol optically inactive but Butan-2-ol is optically active? (c) Although chlorine is an electron withdrawing group, yet it is ortho-, Para- directing in electrophilic aromatic substitution reaction. Why?arrow_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_forwardEach 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_forward
- (a) p-Nitrobenzaldehyde is reactive toward nucleophilic additions than p- more methoxybenzaldehyde. Draw both of the molecular structures and explain the observation. (b) Cyclohexanone forms a cyanohydrin in good yield but 2,2,6-trimethylcyclohexanone does not. Draw both of the molecular structures and explain the observation.arrow_forwardThe hydrocarbon fluorene was treated with potassium t-butoxide in an acid-base reaction, giving the fluorenide anion and t-butyl alcohol. (a) Which way does the equilibrium lie, and by how much? b) What is the proportion of the fluorenide anion to fluorene? (c) Why is fluorene so highly acidic, considering the pKa of an average alkane is above 50?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_forward
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