Homework Answers
II, Malonic ester synthesis
a. Drawn below is the structure for diethyl malonate
b. The mechanism for decarboxylation of malonic acid under basic condiiton followed by acidic workup is shown below.
c. The newly formed C-C bond by malonic ester synthesis and the alkyl or aryl halides needed for the preparation of the given compounds are drawn below.
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The Malonic Acid synthesis is similar to the Acetoacetic Ester synthesis It uses diethyl malonate as...
6. Using either malonic ester synthesis or acetoacetic ester synthesis, outline a reaction scheme in each...
6. Using either malonic ester synthesis or acetoacetic ester synthesis, outline a reaction scheme in each case to show how you will synthesize compounds A and B below. [Show all steps with structure of all intermediates and necessary reagents). A. 3-butyl-2-tetradecanone B. 2-propylpentadecanoic acid
Chapter 22: Mechanisms & the Malonic Ester Name: 1. Propose an arrow.pushing mechanism for the following...
Chapter 22: Mechanisms & the Malonic Ester Name: 1. Propose an arrow.pushing mechanism for the following reaction. Bry Br CH3 CH,COOH U 2. Using the malonic ester (diethyl malonate), synthesize 2-benzylbutanoic acid. ETODE CHAPTER QUESTIONS - CHAPTER 22 3. Using the malonic ester (diethyl malonate), synthesize cyclopentanecarboxylic acid. Eto OEt 4. Draw the structure of three moieties that can undergo decarboxylation. 38 Page
3:48 PM Sun Mar 29 TOO + Chapter 22: Mechanisms & the Malonic Ester Name: Parlu...
3:48 PM Sun Mar 29 TOO + Chapter 22: Mechanisms & the Malonic Ester Name: Parlu 1. Propose an arrow.pushing mechanism for the following reaction contro la 2. Using the malonic ester (diethyl malonate), synthesize 2-benzylbutanoic acid. CHAPTER QUESTIONS - CHAPTER 22 3. Using the malonic ester (diethyl malonate), synthesize cyclopentanecarboxylic acid. 4. Draw the structure of three moieties that can undergo decarboxylation. 38 Parte
11) Show how to synthesize 2-Methylhexanoic acid using the Malonic Ester Synthesis. Start with Diethyl propanedioate...
11) Show how to synthesize 2-Methylhexanoic acid using the Malonic Ester Synthesis. Start with Diethyl propanedioate (C7H1204)
Diethyl malonate can be prepared by the following reaction sequence. Draw the structures of each of...
Diethyl malonate can be prepared by the following reaction sequence. Draw the structures of each of the missing intermediates in the boxes provided. 4. |сH,сH он. 1. Bry PBr3 OH 2. H2O не На NaCN HSO NC CH CH-OH осH сH, CH2 HQ, heat CH2 HCl OEt Et0 How would you prepare each of the following compounds using either an acetoacetic ester synthesis or a malonic ester synthesis? Show all intermediate structures and all reagents 5. COOH
Prepare any THREE of the following molecules, incorporating either an acetoacetic ester synthesis or a malonic...
Prepare any THREE of the following molecules, incorporating either an acetoacetic ester synthesis or a malonic ester synthesis in each synthesis. Show the reagents for each step and the product of each step. Do not draw any mechanisms. CO2Me H2N A B C D
Prepare any THREE of the following molecules, incorporating either an acetoacetic ester synthesis or a malonic...
Prepare any THREE of the following molecules, incorporating either an acetoacetic ester synthesis or a malonic ester synthesis in each synthesis. Show the reagents for each step and the product of each step. Do not draw any mechanisms. CO2Me H2N A B C D
Malonic ester (diethyl malonate) is treated successively with sodium ethoxide (1 eq.), ethyl bromide, potassium tert-butoxide,...
Malonic ester (diethyl malonate) is treated successively with sodium ethoxide (1 eq.), ethyl bromide, potassium tert-butoxide, isobutyl chloride, hot aqueous NaOH HCI, and heat. What is the final product? 6-Methylheptanoic acid • 2-Ethyl-3-methylpentanoic acid HE Ethylisobutylmalonic acid 4-Ethyl-2-methylpentanoic acid 2 Ethyl-4-methylpentanoic acid
Please show the entire mechanism for this problem, thank you! 46) Malonic ester (diethyl malonate) is...
Please show the entire mechanism for this problem, thank
you!
46) Malonic ester (diethyl malonate) is treated successively with sodium ethoxide (1 eq.), 1- bromopentane, potassium tert-butoxide, iodomethane, hot aqueous NaOH, HCl, and heat. What is the final product? a) 2-Methylheptanoic acid b) 3-Methylhexanoic acid c) 3-Methylpentanoic acid d) 2-Methylpentanoic acid e) Ethyl 2-methylheptanoate 47) What would be the major product of the following reaction sequence? 1. BH PCC 1. LDA (-78°C) 2. H,02, OH CH,C12 2. CH3CH,Br ఎంత a)...
A chemist wanted to synthesize the following compound using the acetoacetic acid ester synthesis. Two alkyl...
A chemist wanted to synthesize the following compound using the acetoacetic acid ester synthesis. Two alkyl bromides will be needed for the reaction. Draw the structure of the two required alkyl bromides. Don't draw anything else, just the two alkyl bromides. Насло مکم CH2 alkyl bromide 1 alkyl bromide 2
6. Using either malonic ester synthesis or acetoacetic ester synthesis, outline a reaction scheme in each case to show how you will synthesize compounds A and B below. [Show all steps with structure of all intermediates and necessary reagents). A. 3-butyl-2-tetradecanone B. 2-propylpentadecanoic acid
Chapter 22: Mechanisms & the Malonic Ester Name: 1. Propose an arrow.pushing mechanism for the following reaction. Bry Br CH3 CH,COOH U 2. Using the malonic ester (diethyl malonate), synthesize 2-benzylbutanoic acid. ETODE CHAPTER QUESTIONS - CHAPTER 22 3. Using the malonic ester (diethyl malonate), synthesize cyclopentanecarboxylic acid. Eto OEt 4. Draw the structure of three moieties that can undergo decarboxylation. 38 Page
3:48 PM Sun Mar 29 TOO + Chapter 22: Mechanisms & the Malonic Ester Name: Parlu 1. Propose an arrow.pushing mechanism for the following reaction contro la 2. Using the malonic ester (diethyl malonate), synthesize 2-benzylbutanoic acid. CHAPTER QUESTIONS - CHAPTER 22 3. Using the malonic ester (diethyl malonate), synthesize cyclopentanecarboxylic acid. 4. Draw the structure of three moieties that can undergo decarboxylation. 38 Parte
11) Show how to synthesize 2-Methylhexanoic acid using the Malonic Ester Synthesis. Start with Diethyl propanedioate (C7H1204)
Diethyl malonate can be prepared by the following reaction sequence. Draw the structures of each of the missing intermediates in the boxes provided. 4. |сH,сH он. 1. Bry PBr3 OH 2. H2O не На NaCN HSO NC CH CH-OH осH сH, CH2 HQ, heat CH2 HCl OEt Et0 How would you prepare each of the following compounds using either an acetoacetic ester synthesis or a malonic ester synthesis? Show all intermediate structures and all reagents 5. COOH
Prepare any THREE of the following molecules, incorporating either an acetoacetic ester synthesis or a malonic ester synthesis in each synthesis. Show the reagents for each step and the product of each step. Do not draw any mechanisms. CO2Me H2N A B C D
Prepare any THREE of the following molecules, incorporating either an acetoacetic ester synthesis or a malonic ester synthesis in each synthesis. Show the reagents for each step and the product of each step. Do not draw any mechanisms. CO2Me H2N A B C D
Malonic ester (diethyl malonate) is treated successively with sodium ethoxide (1 eq.), ethyl bromide, potassium tert-butoxide, isobutyl chloride, hot aqueous NaOH HCI, and heat. What is the final product? 6-Methylheptanoic acid • 2-Ethyl-3-methylpentanoic acid HE Ethylisobutylmalonic acid 4-Ethyl-2-methylpentanoic acid 2 Ethyl-4-methylpentanoic acid
Please show the entire mechanism for this problem, thank
you!
46) Malonic ester (diethyl malonate) is treated successively with sodium ethoxide (1 eq.), 1- bromopentane, potassium tert-butoxide, iodomethane, hot aqueous NaOH, HCl, and heat. What is the final product? a) 2-Methylheptanoic acid b) 3-Methylhexanoic acid c) 3-Methylpentanoic acid d) 2-Methylpentanoic acid e) Ethyl 2-methylheptanoate 47) What would be the major product of the following reaction sequence? 1. BH PCC 1. LDA (-78°C) 2. H,02, OH CH,C12 2. CH3CH,Br ఎంత a)...
A chemist wanted to synthesize the following compound using the acetoacetic acid ester synthesis. Two alkyl bromides will be needed for the reaction. Draw the structure of the two required alkyl bromides. Don't draw anything else, just the two alkyl bromides. Насло مکم CH2 alkyl bromide 1 alkyl bromide 2
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