Section C: Propose a two reaction sequence to convert each of the following substrates into the indicated products. Identify the substrate, reagent(s) and catalyst if any used for each reaction (Hint: Each problem will include Aldol or Claisen, Diels Alder, Friedel- Craft's, Grignard or Wittig reaction) (1) (2 OH HO A OH

Section C: Propose a two reaction sequence to convert each of the following substrates into the indicated products. Identify the substrate, reagent(s) and catalyst if any used for each reaction (Hint: Each problem will include Aldol or Claisen, Diels Alder, Friedel- Craft's, Grignard or Wittig reaction) (1) (2 OH HO A OH

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter10: Organohalides

Section10.SE: Something Extra

Problem 19MP: The formation of Br2 from NBS first involves the reaction of NBS with HBr to form an iminol...

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1. Discuss the role of the Aldol condensation reaction in the synthesis below. What specific reaction was used in the synthesis? What is the importance of the aldol reaction in the entire synthetic approach? 2. Show the detailed reaction mechanism involved in their corresponding specific parts in this syntheses.
(a) State and illustrate the following :(i) Wolff-Kishner reduction (ii) Aldol condensation(b) An organic compound (A) which has characteristic odour, on treatment with NaOH forms two compounds (B) and (C). Compound (B) has the molecular formula C7H8O which on oxidation with CrO3 gives back compound (A). Compound (C) is the sodium salt of the acid. Compound (C) when heated with soda lime yields an aromatic hydrocarbon (D). Deduce the structures of (A), (B), (C) and (D). Write chemical equations for all reactions taking place.
(a) Give reasons :(i) CH3—CHO is more reactive than CH3COCH3 towards HCN.(ii) 4-nitrobenzoic acid is more acidic than benzoic acid.(b) Describe the following :(i) Acetylation (ii) Cannizzaro reaction (iii) Cross aldol condensation
Compelling evidence for the existence of a tetrahedral intermediate in nucleophilic acyl substitution was obtained in a series of elegant experiments carried out by Myron Bender in 1951. The key experiment was the reaction of aqueous −OH with ethyl benzoate (C6H5COOCH2CH3) labeled at the carbonyl oxygen with 18O. Bender did not allow the hydrolysis to go to completion, and then examined the presence of a label in the recovered starting material. He found that some of the recovered ethyl benzoate no longer contained a label at the carbonyl oxygen. With reference to the accepted mechanism of nucleophilic acyl substitution, explain how this provides evidence for a tetrahedral intermediate.
Compelling evidence for the existence of a tetrahedral intermediate in nucleophilic acyl substitution was obtained in a series of elegant experiments carried out by Myron Bender in 1951. The key experiment was the reaction of aqueous−OH with ethyl benzoate (C6H5COOCH2CH3) labeled at the carbonyl oxygen with 18O. Bender did not allow the hydrolysis to go to completion, and then examined the presence of a label in the recovered starting material. He found that some of the recovered ethyl benzoate no longer contained a label at the carbonyl oxygen. With reference to the accepted mechanism of nucleophllic acyl substitution, explain how this provides evidence for a tetrahedral intermediate.
The (+) - aureol is a natural product that has shown selective activity against certain colon and lung cancer cell lines. It is postulated that a key step in the biosynthesis of this substance is the conversion of carbocation A into B. Propose a possible mechanism for this transformation (MUST show the corresponding arrows).
(a) Account for the following :(i) CH3CHO is more reactive than CH3COCH3 towards reaction with HCN.(ii) Carboxylic acid is a stronger acid than phenol.(b) Write the chemical equations to illustrate the following name reactions:(i) Wolff-Kishner reduction (ii) Aldol condensation (iii) Cannizzaro reaction
4. Give the structure of compounds A to E in the following reaction sequence.
A) Provide a reasonable multistep synthesis of the following molecule from the indicated starting material, using any reagents necessary. Please include both a retrosynthesis and a forward synthesis (that includes the product and reagents of each individual step in your synthesis). B) If you started with 1 mole of starting material and each step of your synthesis gave 100% yield, how many moles of the product drawn would you end with?
Choose the set of letters corresponding to the BEST answer. -gives two moles of QRS upon hydrolysis -the most reactive towards nucleophilic acyl substitution -can be formed from the alcoholysis of TUV -has the most acidic proton
Over the past several decades, chemists have developed a number of synthetic methodologies for the synthesis of steroid hormones. One of these, developed by Lutz Tietze at the Institut für Organische Chemie der Georg-August-Universität, Göttingen, Germany, used a double Heck reaction to create ring B of the steroid nucleus. As shown in the following retrosynthetic analysis, a key intermediate in his synthesis is compound (1). Two Heck reaction disconnects of this intermediate give compounds (2) and (3). Compound (2) contains the aromatic ring that becomes ring A of estrone. Compound (3) contains the fused five- and six-membered rings that become rings C and D of estrone. Q.Propose structural formulas for compounds (2) and (3).
Over the past several decades, chemists have developed a number of synthetic methodologies for the synthesis of steroid hormones. One of these, developed by Lutz Tietze at the Institut für Organische Chemie der Georg-August-Universität, Göttingen, Germany, used a double Heck reaction to create ring B of the steroid nucleus. As shown in the following retrosynthetic analysis, a key intermediate in his synthesis is compound (1). Two Heck reaction disconnects of this intermediate give compounds (2) and (3). Compound (2) contains the aromatic ring that becomes ring A of estrone. Compound (3) contains the fused five- and six-membered rings that become rings C and D of estrone. Q.Name the types of functional groups in estrone