7. Starting with an alkyl bromide, outline an efficient Wittig synthesis for the target alkene (1) shown below. 1 a) Show the structure of your alkyl bromide, and how it reacts with (Ph);P to form the Wittig salt. b) Show the Wittig salt and how it reacts with a strong base to form the ylide. For strong base you can use sodium ethoxide (EtONa). c) Show the two resonance structures of the ylide formed above. d) Show how the ylide reacts with an aldehyde or ketone of your choice to form the target alkene (1).

7. Starting with an alkyl bromide, outline an efficient Wittig synthesis for the target alkene (1) shown below. 1 a) Show the structure of your alkyl bromide, and how it reacts with (Ph);P to form the Wittig salt. b) Show the Wittig salt and how it reacts with a strong base to form the ylide. For strong base you can use sodium ethoxide (EtONa). c) Show the two resonance structures of the ylide formed above. d) Show how the ylide reacts with an aldehyde or ketone of your choice to form the target alkene (1).

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

See similar textbooks

Similar questions

Draw the major organic product you would expect to isolate from the reaction of p-bromoethoxybenzene with a misture of HNO3HNO3 and H2SO4H2SO4.
Arrange the structure on the image with regard to the reactivity towards hydrolysis. 1 being the least and 3 being the most
1. i)Give the structure of the product from the reaction of propanal with 1M ethanol in dry acid . ( II)What happens when further 1M of ethanol is added to the above
Arrange the structure on the image with regard to the reactivity towards nucleophilic acyl substitution 1 being the least and 3 being the most
Propose a short synthesis f or ONE of the following molecules. You can start with acetylene, and alkyl halides from 1-4 carbons in length. You can also use an reagents you wish. a) Hexan-3-one (CH3CH2COCH2CH2CH3)
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).
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.
A key step in the synthesis of naproxen, an NSAID more commonly known by its brand name, Aleve (Section 3.9), is a coupling reaction of 2-bromo-6-methoxynaphthalene to form 2-methoxy-6-vinylnaphthalene. Show three different coupling reactions, and the required reagents, that could be used tocarry out this step.
I need specific description of the compounds involved in the synthesis (functional groups, specific features). and also describe the steps involved in the synthesis and the role of each step. And most important！！devote one to each step of the synthesis. Each step should clearly indicate the reagent used, the stereochemistry involved in the reaction and its importance or relevance to the multistep synthesis
(a) What reagents would be used for the conversion of alkene A into the target? (b) What reaction is involved in the conversion of alcohol B into alkene A? Suggest a reagent that might affect this transformation. (c) Give a retrosynthetic analysis showing the disconnection of B, the synthons produced that lead to the synthetic equivalents given (draw their structures).
Draw the detailed reaction mechanism of the vilsmeier hack reaction: preparation of indole-3-carboxaldehyde, using indole, POCl3, DMF, NaOH, and H2O. Include arrows in the mechanism.
1. Outline the synthesis of 2-pentyne from ethyne and alkyl halides of appropriate structures