The primary amine isoamylamine (3-methylbutylamine) occurs naturally in a number of fruits and is used as a food flavouring: (CH,),CHCH,CH,NH, 3-methylbutylamine Suggest two ways in which it can be synthesised from suitable organic precursors. Note that only one of the two methods you propose may involve the reduction of another nitrogen containing compound. In each case, you should indicate what starting material and other reagents are needed, though details of precise experimental conditions or reaction mechanisms are not required.

The primary amine isoamylamine (3-methylbutylamine) occurs naturally in a number of fruits and is used as a food flavouring: (CH,),CHCH,CH,NH, 3-methylbutylamine Suggest two ways in which it can be synthesised from suitable organic precursors. Note that only one of the two methods you propose may involve the reduction of another nitrogen containing compound. In each case, you should indicate what starting material and other reagents are needed, though details of precise experimental conditions or reaction mechanisms are not required.

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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(a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) (1) Ph Ph 836 Ph THF A 1 B H₂SO4 100 °C 3 OH Which of the two methods (A or B) is more likely give high yield of methylenecyclohexane 2? Briefly explain.
(a) Give chemical tests to distinguish between :(i) Propanol and propanone (ii) Benzaldehyde and acetophenone(b) Arrange the following compounds in an increasing order of their property as indicated :(i) Acetaldehyde, Acetone, Methyl tert-butyl ketone (reactivity towards HCN)(ii) Benzoic acid, 3,4-Dinitrobenzoic acid, 4-Methoxybenzoic acid (acid strength)(iii) CH3CH2CH (Br) COOH, CH3CH (Br) CH2COOH, (CH3)2CHCOOH (acid strength)
(b) Answer BOTH parts (i) and (ii). (i) Using your knowledge of silicon chemistry, explain why the synthesis of a compound containing a formal Si=0 double bond is challenging. (ii)Bearing in mind your answer to part (i), suggest a synthetic route to a silanone, R2Si=O, starting from silicon tetrachloride SiCl4 and using any other reagents you choose. Identify all reagents and side-products in your synthetic route and specify your chosen R group, giving reasons for your choice.
Predict the coupling products of organometallic substitutions, and use them in syntheses.
1. (a) Compound A,B and C are isomers with molecular formula of C4H8O. When compound A,B and C reacts with 2,4-dinirophenylhydrazine, a yellow precipitate is formed. Compound B and C show a positive result with silver nitrate in aqueous ammonia. (i) Deduce the structures of A,B and C. (ii) Give the observation when A and B reacts with silver nitrate in aqueous ammonia.
Predict the products and propose mechanisms for the reactions of ketones and aldehydes with oxidizing and reducing agents, amines, alcohols, and phosphorus ylides.
1. (a) Compound A,B and C are isomers with molecular formula of C4H8O. When compound A,B and C reacts with 2,4-dinirophenylhydrazine, a yellow precipitate is formed. Compound B and C show a positive result with silver nitrate in aqueous ammonia. (i) Deduce the structures of A,B and C. (ii) Give the observation when A and B reacts with silver nitrate in aqueous ammonia.
(i) The enolisation of ketone A can generate an equilibrium mixture of A and either enol B or enolate C. Give the structure of both B and C, and the mechanism for their formation from A under the given conditions. (ii) A HCI (cat.) NaOH (cat.) B с Draw the structure of the product obtained when A is dissolved in D3O*. Give a detailed mechanism to account for the structure you propose.
Provide one alkyl halide of your choice and discuss its structure, nomenclature (systematic and common), physical properties, method/s of preparation, and applications.
Aspirin, or 2-acetoxybenzoic acid, (C9H8O4) is often synthesised from salicylic acid.(i) Sketch and discuss any changes in the number of possible structural conformations ofaspirin relative to those of salicylic acid. (ii) Re-draw the structure predicted to be the lowest energy conformation of aspirin,indicating any expected stabilising and destabilising interactions. Justify your choice.
(b) Answer ALL parts (i)-(iv) of this question. The scheme below outlines a synthesis of a vitamin A analogue. (i) Suggest reagents for the conversion of 1 into 2 and write a mechanism for this reaction; (ii) Suggest a reagent for the conversion of 3 into 4; (iii) Propose a mechanism for the conversion of 4 into 5; (iv) Suggest reagents for the conversion of 5 into 6 and provide a mechanism for this transformation. reagents? 2 reagents? PPH3; HBr ÓH 3 4 PPH3 Br reagents?
(b) (i) The reaction between aromatic compound W, C,H$OC1 with an amine X, CH>N was carried out. The compound Y was extracted and purified from this reaction. It was then reduced by LİAIH4 followed by hydrolysis to obtain compound Z, which is a tertiary amine. Draw the structures for compounds W, X, Y and Z.