Show by writing a suitable series of synthetic steps and intermediates how you could prepare two (2)of the following compounds starting from acetylene ( HC=CH), and any other nectssary organic orinorganic reagents. You must choose one from group "A" and one from group "B."28.AОНii)i)iv)iii)2oulng cont edr lo eoindruaup siou Isupa soobowg bluow (-1) theuopo r to ono doidw siriaf rd bowollot onoso nn zaw ti trofw woled botallo sao doioboug bluow (-) chopdriw batanHO.elaubort(bormoOH20er

Synthesis of product (iii) from group A:

Answered: Show by writing a suitable series of…

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter21: Nas: Nucleophilic Aromatic Substitution

Section: Chapter Questions

Problem 7E

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8.30 Outline an efficient synthesis of each of the following compounds from the indicated starting material and any necessary organic or inorganic reagents: (d) NCCH2CH2CN from ethyl alcohol (e) Isobutyl iodide from isobutyl chloride (f) Isobutyl iodine from tert-butyl chloride
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.
Compelling evidence for the existence of a tetrahedral intermediate innucleophilic acyl substitution was obtained in a series of elegantexperiments carried out by Myron Bender in 1951. The key experimentwas the reaction of aqueous −OH with ethyl benzoate (C6H5COOCH2CH3)labeled at the carbonyl oxygen with 18O. Bender did not allow thehydrolysis to go to completion, and then examined the presence of alabel in the recovered starting material. He found that some of therecovered ethyl benzoate no longer contained a label at the carbonyloxygen. With reference to the accepted mechanism of nucleophilic acyl substitution, explain how this provides evidence for a tetrahedralintermediate.
a) Write out the first 3 steps only(to the tetrahedral intermediate shown) in the 6-step arrow pushing mechanism showing how ethyl propanoate is hydrolyzed in acid to form propanoic acidand ethanol. b) NaOH/H2O also serveto hydrolyze an ester; briefly explain why NaOH/H2Ois generally preferable.
3. a. Write the complete reaction equation and give the name off all product (s) from the following reaction:i. bromination of phenolii. benzoic acid and ethylchloride in the presence of AlCl3b. Design the synthesis of two following compounds.i. m- chloropropiophenone from benzeneii. p-bromonitrobenzoic acid from toluene
Propose a brief and efficient synthesis of 4-propylheptan-4-ol, starting from 1-bromopropane and CO2 as your only source of carbon atoms. You may use any other reagents as necessary.
A student in Ochem proposed the following synthesis. Explain the problem with this approach and provide the necessary reagents to convert halohydrin A to alkene B (more than one step is required) in addition provide the product after each step. Provide the mechanism and expected actual final product from the reaction of halohydrin A with LDA
1. Write equations, using displayed formulae, to show the conversion of but-1-eneinto:a) polybut-1-eneb) 1,2-dibromobutane 2. a) Explain why alkenes tend to react with electrophiles.b) Show the mechanisms for the following reactions:i) ethene with bromineii) but-2-ene with hydrogen bromidec) Explain how bromine can behave as an electrophile. 3. Reaction of but-1-ene with HBr gives two products in unequal amounts. In eachcase, identify the two products, state which is the major product, explain why it isthe major product and give the mechanism for its formation.
1.Describe the ozonolysis of alkenes 2.one mole of a hydrocarbon(A) reacts with one mole of beomine giving a dibromo compound C5H10Br2.Substance A on treatment with cold dilute kMnO4 solution forms a compound C5C12O2(C5H12O2) on ozonolysis A,gives equimolar quantities of propanone and ethanol.Deduce the structure of substance A.
Suggest the most appropriate method for each of the following laboratory syntheses. Ineach case, suggest both a chromium reagent and a chromium-free reagent. butan@2@ol ¡ butan@2@one, CH3COCH2CH3
Doxaprost, an orally active bronchodilator patterned after the natural prostaglandins , is synthesized in the following series of reactions starting with ethyl 2-oxocyclopentanecarboxylate. Except for the Nef reaction in Step 8, we have seen examples of all other types of reactions involved in this synthesis. Q. Propose a set of experimental conditions to bring about the alkylation in Step 1. Account for the regioselectivity of the alkylation (i.e., that it takes place on the carbon between the two carbonyl groups rather than on the other side of the ketone carbonyl).

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