EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
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Question
Chapter 23, Problem 23.21P
Interpretation Introduction
Interpretation:
The formation of trimethylammonium iodide as a product of the given reaction by the use of a sequence of reaction which represents deprotonation-alkylation is to be stated.
Concept introduction:
Deprotonation is defined as the removal of a proton from a Bronsted–Lowry acid in an acid-base reaction. The species formed when acid loses its proton is known as a conjugate base. Alkylation is defined as the addition of an alkyl group.
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Students have asked these similar questions
(b) Suggest a reasonable biosynthesis for the naturally occurring alkaloid
coniine (isolated from hemlock), starting from octanoic acid.
Coniine
Answer BOTH parts of this question.
(a) Briefly explain the origin of amine basicity. Using resonance structures explain why
aniline is a weaker base than methylamine.
(b) Draw the structure of compound X and provide a curly arrow mechanism for the
reduction in Scheme 1.
X
1. NaBH4
2. H₂O
Scheme 1
OH
(a) Isoleucine has been prepared by the following sequence of reactions. Give the structure of compounds A through D isolated as intermediates in this synthesis.(b) An analogous procedure has been used to prepare phenylalanine. What alkyl halide would you choose as the starting material for this synthesis?
Chapter 23 Solutions
EBK ORGANIC CHEMISTRY
Ch. 23 - Prob. 23.1PCh. 23 - Prob. 23.2PCh. 23 - Prob. 23.3PCh. 23 - Prob. 23.4PCh. 23 - Prob. 23.5PCh. 23 - Prob. 23.6PCh. 23 - Prob. 23.7PCh. 23 - Prob. 23.8PCh. 23 - Prob. 23.9PCh. 23 - Prob. 23.10P
Ch. 23 - Prob. 23.11PCh. 23 - Prob. 23.12PCh. 23 - Prob. 23.13PCh. 23 - Prob. 23.14PCh. 23 - Prob. 23.15PCh. 23 - Prob. 23.16PCh. 23 - Prob. 23.17PCh. 23 - Prob. 23.18PCh. 23 - Prob. 23.19PCh. 23 - Prob. 23.20PCh. 23 - Prob. 23.21PCh. 23 - Prob. 23.22PCh. 23 - Prob. 23.23PCh. 23 - Prob. 23.24PCh. 23 - Prob. 23.25PCh. 23 - Prob. 23.26PCh. 23 - Prob. 23.27PCh. 23 - Prob. 23.28PCh. 23 - Prob. 23.29PCh. 23 - Prob. 23.30PCh. 23 - Prob. 23.31PCh. 23 - Prob. 23.32PCh. 23 - Prob. 23.33PCh. 23 - Prob. 23.34PCh. 23 - Prob. 23.35PCh. 23 - Prob. 23.36PCh. 23 - Prob. 23.37PCh. 23 - Prob. 23.38PCh. 23 - Prob. 23.39PCh. 23 - Prob. 23.40PCh. 23 - Prob. 23.41PCh. 23 - Prob. 23.42PCh. 23 - Prob. 23.43PCh. 23 - Prob. 23.44APCh. 23 - Prob. 23.45APCh. 23 - Prob. 23.46APCh. 23 - Prob. 23.47APCh. 23 - Prob. 23.48APCh. 23 - Prob. 23.49APCh. 23 - Prob. 23.50APCh. 23 - Prob. 23.51APCh. 23 - Prob. 23.52APCh. 23 - Prob. 23.53APCh. 23 - Prob. 23.54APCh. 23 - Prob. 23.55APCh. 23 - Prob. 23.56APCh. 23 - Prob. 23.57APCh. 23 - Prob. 23.58APCh. 23 - Prob. 23.59APCh. 23 - Prob. 23.60APCh. 23 - Prob. 23.61APCh. 23 - Prob. 23.62APCh. 23 - Prob. 23.63APCh. 23 - Prob. 23.64APCh. 23 - Prob. 23.65APCh. 23 - Prob. 23.66APCh. 23 - Prob. 23.67APCh. 23 - Prob. 23.68APCh. 23 - Prob. 23.69APCh. 23 - Prob. 23.70APCh. 23 - Prob. 23.71APCh. 23 - Prob. 23.72APCh. 23 - Prob. 23.73APCh. 23 - Prob. 23.74APCh. 23 - Prob. 23.75APCh. 23 - Prob. 23.76APCh. 23 - Prob. 23.77APCh. 23 - Prob. 23.78APCh. 23 - Prob. 23.79APCh. 23 - Prob. 23.80APCh. 23 - Prob. 23.81AP
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Similar questions
- (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_forward3) Draw equations of the following reactions and and explain to which direction is the respective quillibrium shifted. a) cyclohexylamine + water b) aniline + sulphuric acid c) triethylamine + acetic acidarrow_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
- Outline syntheses of each of the following from aniline and any necessary organic or inorganic reagents. (a) p-Nitroaniline (b) 2,4-Dinitroaniline (c) p-Aminoacetanilidearrow_forwardthe following reaction scheme leads to the formation of compound B. give the structure of the final products and of the intermediate product A and justify, using the mechanism, the formation of thesearrow_forwardHow would you account for the following :(a) Electrophilic susbstitution in case of aromatic amines takes place more readily than benzene.(b) Ethanamide is a weaker base than ethanamine.arrow_forward
- Safrole, which is isolated from sassafras (Problem 21.33), can be converted to the illegal stimulant MDMA (3,4- methylenedioxymethamphetamine, “Ecstasy”) by a variety of methods. (a) Devise a synthesis that begins with safrole and uses a nucleophilic substitution reaction to introduce the amine. (b) Devise a synthesis that begins with safrole and uses reductive amination to introduce the amine.arrow_forwardSafrole, which is isolated from sassafras (Problem 21.33), can be converted to the illegal stimulant MDMA (3,4-methylenedioxymethamphetamine, "Ecstasy") by a variety of methods. (a) Devise a synthesis that begins with safrole and uses a nucleophilic substitution reaction to introduce the amine. (b) Devise a synthesis that begins with safrole and uses reductive amination to introduce the amine. NHCH9 MDMA safrolearrow_forwardAnswer ALL parts of this question. (a) Compound Z is a tertiary aromatic amine with the formula, C8H11N. Provide a chemical structure for compound Z. (b) Provide a reaction scheme for the preparation of nitrous acid. (c) Draw the structure of the product formed exclusively when nitrous acid reacts with Z. (d) Give a curly arrow mechanism for the preparation of the yellow azo-dye from the reaction of Z with benzenediazonium chloride.arrow_forward
- Give reasons :(i) Electrophilic substitution in aromatic amines takes place more readily than benzene.(ii) CH3CONH2 is weaker base than CH3CH2NH2.arrow_forward24.82 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_forward(a) Explain why an alkylamine is more basic than ammonia?(b) How would you convert(i) Aniline to nitrobenzene (ii) Aniline to iodobenzenearrow_forward
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