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1 1.30202 Organic Chemistry 1/2024 Assignment 5/ (As Experimental #6) Question 1. Using Hell-Volhard Zelinsky Reaction. Derive the product showing the appropriate mechanism involved (5 marks). Question 2. Study the reaction of the following Beta-dicarbonyl compounds. Several steps are required to produce the product. Answer following questions below: a) Show the alkylation reaction with an appropriate halide (3 marks) b) What would happen to the product achieved in (a) under hydrolysis? (2 mark) c) What would happen if heat is applied to product obtained in (b)? (2marks) d) Show the complete reaction staring from (a) to (c). (3) 2 Question 3. Esters can be prepared using a number of methods. Carboxylic acids are amongst the most common starting materials in many of these methods. Explain how to synthesis the following ester using one method showing its mechanism. (5 marks) Question 4 a. Show how you can convert a carboxylic acid to an acid chloride using two different methods – use acetic acid (CH3COOH) as an example (2 marks). b. Why are acid chlorides the most common acid halide that is used in organic chemistry when it is perfectly okay to also use acid bromides and iodides? (2 marks) c. If you were to synthesis butanoyl chloride, how would you go about doing it? Explain what reagent you would use to prepare the target product (3 marks) Question 5. (a) Explain why acetic acid is a stronger base than ethanol (2mks) (b) Explain why acetamide is a weak base than ethylamine (2mks) (c) Tricholoroacetic acid is a strong acid that acetic acid, why? (2mks Question 6. (a) Show how you would synthesis N-methylacetamide with acetic acid (3marks) H3C O OH H3C O N H CH3 (b) Explain why 2-methyl-2-butanol is obtained as the product when ethyl propanoate is treated with excess amount of methyl magnesium bromide, instead of butanone! (3marks) 3 O O CH3 + CH3MgBr OH CH3 H3C H3C (c) Explain why ethyl amine is obtained when ethanamide is treated with lithium aluminium hydride (3 marks) H3C O NH2 + LiAlH4 H3C N H H Question 7. Show how you can prepare ethyl 2,4-diphenyl-3-oxobutanoate (a β-keto ester) via a Claisen condensation reaction with the starting material phenyl acetic acid (4marks) OH O O CH3 O Question 8. Show how Aldol reaction and Claisen reaction are closely related to one another and also where they differ? Use the following to illustrate your answer. (4 marks) O CH3 base O HO CH3 an aldol reaction H3C O O CH3 base A Claisen reaction H3C O CH3 O O CH3 Question 9. State the difference observed between an acetoacetic ester synthesis and Malonic ester synthesis.
May 11, 2024
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