a)
Interpretation:
The product of the two step process shown is to be given and complete electron-pushing mechanism for its formation also is to be provided.
Concept introduction:
The terminal
To propose:
The product of the two step process shown and to give a complete electron-pushing mechanism for its formation.
b)
Interpretation:
The product of the two step process shown is to be given and complete electron-pushing mechanism for its formation also is to be provided.
Concept introduction:
The terminal alkynes being acidic form sodium alkynides when treated with bases like sodium amide. The alkynides when treated with alkyl halides yield the higher alkynes as the product. The alkynide ion being nucleophilic attacks the positively polarized carbon of C-X bond in alkyl halides displaces the halogen to yield the higher alkyne as the product.
To propose:
The product of the two step process shown and to give a complete electron-pushing mechanism for its formation.
c)
Interpretation:
The product of the two step process shown is to be given and complete electron-pushing mechanism for its formation also is to be provided.
Concept introduction:
The terminal alkynes being acidic form sodium alkynide when treated with bases like sodium amide. The alkynides when treated with alkyl halides yield the higher alkynes as the product. The alkynide ion being nucleophilic attacks the positively polarized carbon of C-X bond in alkyl halides displaces the halogen to yield the higher alkyne as the product.
To propose:
The product of the two step process shown and to give a complete electron-pushing mechanism for its formation.
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Chapter 9 Solutions
Organic Chemistry
- 4) Draw the complete electron-pushing arrow mechanism for the following reductions. Explain, using resonance contributors, the regiochemistry that results in each case. ỌMe Na, MeOH ? NH3 CHO Na, MeOH ? NH3arrow_forwardPropose a multi-step synthetic route to form the polycyclic molecule on the right hand side using the following reagents on the left hand side of the arrows: i) cyclic ketone; ii) a,ẞ-unsaturated ketone; iii) either the organocuprate OR the organolithium reagent listed; and ii) any other reagents or solvents of your choosing The depicted reagents represent all necessary building blocks that are directly incorporated into the molecule on the right, however you should use additional reagents to help facilitate its construction based on Chem 110 content from Chapters 21 and 23. This is a multi-step synthesis and not all reagents will be used at the same time. When describing your solution, show the stable intermediates along your proposed synthetic route and number the individual synthetic steps. You do not have to worry about stereochemistry in this particular question. For two (2) of your proposed steps, show individual mechanistic arrows that show the flow of electrons during that…arrow_forward4. identify the structure of A and B in the following synthetic scheme: Write out complete reactions for each step, showing the structure of all reactants and products. (a) cyclohexanol +Na2Cr2O7/H2SO4, H2O -------> A (b) A + Et2NH/H2SO4 ----->Barrow_forward
- A problem often encountered in the oxidation of primary alcohols to acids is that esters are sometimes produced as by-products. For example, oxidation of ethanol yields acetic acid and ethyl acetate: Propose a mechanism to account for the formation of ethyl acetate. Take into account the reversible reaction between aldehydes and alcohols:arrow_forwardNonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardWrite a reaction equation sequence for the following synthetic conversion. Eachreaction step must be represented by a complete reaction equation in which substrate,reagents and products are shown. Mechanisms are not required.arrow_forward
- Show how to accomplish the following alkylation. (a) Step 1 (i) Specify the reagent used in this step. (ii) Draw the structure of the intermediate formed in this step, compound A. (B) draw the structure of the reagent needed for this step. (C) specify the reagent used in step b C Show how to accomplish the following alkylation. [References] Step 1 Step 2 compound A Step 3 CO₂Et (a) Step 1 (i) Specify the reagent used in this step. (ii) Draw the structure of the intermediate formed in this step, compound A. 1arrow_forward1) Draw the complete electron-pushing arrow mechanism for the following reductions. Explain, using resonance contributors (structures), the regiochemistry that results in each case. OMe Na, MeOH ? NH3 CHO Na, MeOH ? NH3arrow_forwardProvide the missing component that completes the following reactionsarrow_forward
- b) The Wolf-Kishner reduction is a reaction used in Organic Chemistry to convert carbonyl functionalities into methylene group. The reaction was used to convert an aldehyde or ketone to an alkane using hydrazine, base and thermal conditions. The mechanism begins with the attack of hydrazine of the aldehyde or ketone. Stage 1: The reaction of aldehyde/ketone with hydrazine to produce hydrazine Stage 2: Reaction with the base and heat to convert hydrozone to alkane Write the mechanism of the reaction.arrow_forwardComplete synthesis, show reagents and intermediate compounds.arrow_forwardConsider the following reaction. + PhLi (2 eq.) then water a) Propose a structure for the final product. b) Give a complete mechanism for the transformation. c) Draw an energy diagram of the transformation and briefly comment on the relative energies of the starting material, final product, and any intermediate(s), and about the rate determining step.arrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning