Reaction 2:(p)Consider the following reaction that proceeds via a concerted mechanism. Add arrowsto indicate the movement of electrons.OCH3OCH3(e)The electrophile in the reaction in part (d) is ethylene (H2CCH2). Circle the orbital of theelectrophile that must overlap with the nucleophile orbital in this reaction.(f)nonbonding lone pairnonbonding pσC-COC-0σC-HπC-Cσ*C-Cσ*C-0σ*C-Hπ*C-CIn going from reactants to products in the reaction in part (d), does entropy increase,decrease, or stay about the same?

d) Mechanism:The reaction you've presented is a classic example of a pericyclic reaction,…

Answered: Reaction 2: (p) Consider the following…

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter25: Enolate & Enol Nucleophiles

Section: Chapter Questions

Problem 7E

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Reaction 2: (d) Consider the following reaction that proceeds via a concerted mechanism. Add arrows to indicate the movement of electrons. OCH3 OCH3 (e) The electrophile in the reaction in part (d) is ethylene (H2CCH2). Circle the orbital of the electrophile that must overlap with the nucleophile orbital in this reaction. (f) nonbonding lone pair OC-C OC-0 OC-H TC-C nonbonding p σ*C-C σ*C-0 σ*C-H π*C-C In going from reactants to products in the reaction in part (d), does entropy increase, decrease, or stay about the same?
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 ? NH3
For an SN1 reaction, which of the following is the correct order from the given statements below: (1) The nucleophile attacks both from the front and from the back of the planar carbocation. (II) The nucleophile attacks from a backside position. (II) The halide ion as the leaving group leaves initially. (IV) The halide ion as the leaving group leaves subsequently. (V) The halide ion as the leaving group leaves simultaneously as the nucleophile approaches. (VI) The product is formed. (VII) A stable carbocation is formed. (VIII) A product with inversed chirality is formed. Nu R-C-X + R-C-Nu wh
Kindly answer question a & b
For each of the following pairs of species, which has the strongest nucleophile in acetone?
4. The given mechanism tracks the transformation of a primary hydroxyl FG into an aldehyde carbonyl using the Swern oxidation ([0]) conditions. Examine the details of the mechanism, paying close attention to the lack of lone pairs, and then respond to the following questions. Note that "reaction arrow" refers to the arrows that separate the reaction steps. (a) Draw a box around the pE2 step (reaction arrow) of the mechanism. (b) Draw a star on any addition (Ad) step (reaction arrow) of the mechanism. (c) Draw a circle around any elimination (E) step (reaction arrow) of the mechanism. (d) When the Swern conditions are characterized as NOT over-oxidizing primary hydroxyl FGs into carboxyl FGs, to what step in the mechanism does this refer? (e) What is the leaving group for the pE2 step in this mechanism? What criteria is used to judge what makes this FG a good leaving group? H3C S=0 H3C H3C → OS- H3C CO2 CO CIO CH2 H3C H3C CH3 H3C H3C H3C CH3 H. H3C O CH3 H3C H NET3 H3C H3C H3C R R NET3
Jj.153.
Each of the following may participate in an elimination reaction, under the proper conditions. (a) Circle the alpha (a) carbon. (b) Circle the beta (B) carbon(s). (c) Draw the alkene product(s) that may form, with the new double bond between the a and ß positions. (d) If more than one alkene product is possible, circle the most stable (Zaitsev) product. A В J C K E F G 33-0
(d) Consider the following catalyzed and non-catalyzed pathways of a substitution reaction of bromoethane. Draw an energy diagram for each of the following reactions (label all axes and include reactants, intermediates (if any) and products). CH3CH₂Br + HO CH³CH₂OH + B (non-catalyzed) ное CH3CH₂Br + CH3CH₂OH + 1 (catalyzed) CH3CH₂ + Br
(b) Consider the reaction of 1-bromobutane with a large excess of ammonia (NH3). Draw the reactants, the transition state, andthe products. Note that the initial product is the salt of an amine (RNH3+ Br - ), which is deprotonated by the excess ammonia to give the amine.
Consider the SN2 reaction of butyl bromide with OH- ion. CH3CH2CH2CH2B + OH- → CH3CH2CH2CH2OH + Br Assuming no other changes, what effect on the rate would result from simultaneously doubling the concentrations of both butyl bromide and the OH- ion? Draw the curved arrow mechanism for the SN1 reaction of methanol with tert-butyl iodide. Next, draw an Energy vs. Reaction Coordinate diagram for this reaction, labeling all transition states as "TS" and intermediates as appropriate for those drawn in the mechanism above, showing the relative energies on the diagram.
b) Explain in detail what characteristics of the alkyl halide influence whether a mechanism will be SN1 or SN2. c) Explain in detail what characteristics of a nucleophile influence whether a reaction will be SN1 or SN2.

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