5. Predict the organic products of the following nucleophilic substitution reactions, all of which are carried out in polar aprotic solvent. Identify the nucleophile, electrophile, and the leaving group. Predict the mechanistic pathway this reaction will follow. Explain why? S¯Na+ +
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![5. Predict the organic products of the following nucleophilic substitution reactions, all of which are carried out
in polar aprotic solvent. Identify the nucleophile, electrophile, and the leaving group.
Predict the mechanistic pathway this reaction will follow. Explain why?
S¯Na+
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- For the given SN2 reaction, draw the organic and inorganic products of the reaction, and identify the nucleophile, substrate, and leaving group. Include wedge-and-dash bonds and draw hydrogen on a stereocenter. Hmm.. CEN + CI Organic product Inorganic productThe S 1 mechanism starts with the rate-determining step which is the dissociation of the alkyl halide into a carbocation and a halide ion. The next step is the rapid reaction of the carbocation intermediate with the nucleophile; this step, completes the nucleophilic substitution stage. The step that follows the nucleophilic substitution is a fast acid-base reaction. The nucleophile now acts as a base to remove the proton from the oxonium ion from the previous step, to give the observed product. Draw a curved arrow mechanism for the reaction, adding steps as necessary. Be sure to include all nonzero formal charges. Draw or edit atoms, groups, or bonds Add/Remove step 2 9 Click and drag to start drawing a structure. aleFor the given Sy2 reaction, draw the organic and inorganic products of the reaction, and identify the nucleophile, substrate, and leaving group. Include wedge-and-dash bonds and draw hydrogen on a stereocenter. :CEN Organic product Inorganic product + Draw the organic product. Draw the inorganic product. Incorrect
- Substitution reactionBr Brz CH3 CH3 H3C CH2CI2 H3C Br Electrophilic addition of bromine, Br2; to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl). In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br: :Br: .CH3 H3C H3C CH3 Br:Determine whether the following reaction is an example of a nucleophilic substitution reaction: O" Molecule A + NO₂ Molecule B NO₂ + H
- Alcohols are acidic in nature. Therefore, a strong base can abstract the acidic hydrogen atom of the alcohol in a process known as deprotonation. The alcohol forms an alkoxide ion by losing the proton attached to the oxygen atom of the hydroxyl ( -OH) group. The alkoxide formed can act as a base or a nucleophile depending on the substrate and reaction conditions. However, not all bases can abstract the acidic proton of alcohols and not all alcohols easily lose the proton. Deprotonation depends on the strength of the base and the acidity of the alcohol. Strong bases, such as NaNH2, can easily abstract a proton from almost all alcohols. Likewise, more acidic alcohols lose a proton more easily. Determine which of the following reactions would undergo deprotonation based on the strength of the base and the acidity of the alcohol. Check all that apply. ► View Available Hint(s) CH3CH,OH + NH3 →CH,CH,O-NH CH3 CH3 H3C-C-H+NH3 → H3 C-C-H OH O-NH CH3CH2OH + NaNH, → CH3CH,O-Na* + NH3 CHC12 Cl₂…Draw the most stable resonance form for the intermediate in the following electrophilic substitution reaction. LOCH3 LOCH3 HNO3 / CH3CO₂H O₂N • You do not have to consider stereochemistry. • Include all valence lone pairs in your answer. ● In cases where there is more than one answer, just draw one.For the following substitution reaction, which statement is FALSE? NaOH Br HO, Increasing the concentration of hydroxide will cause an increase in the rate of reaction. The reaction proceeds via a carbocation intermediate. process is bimolecular. The use of a polar aprotic solvent will enhance the rate.
- LOH NaOH `N' (S) H20 'N' ČI This nucleophilic substitution occurs with rearrangement. Draw curved arrows to show the movement of electrons in the following step of the reaction mechanism. Arrow-pushing Instructions OH :OH N. H.Acyl transfer (nucleophilic substitution at carbonyl) reactions proceed in two stages via a "tetrahedral intermediate." Draw the tetrahedral intermediate as it is first formed in the following reaction. CI H₂N OH • You do not have to consider stereochemistry. • Include all valence lone pairs in your answer. • Do not include counter-ions, e.g., Na+, I, in your answer. • In cases where there is more than one answer, just draw one. Sn [Fmethanol + CH3OH Suppose you were told that the above reaction was a substitution reaction but you were not told the mechanism. Evaluate the following categories to determine the reaction mechanism and then draw the structure of the major organic product. Type of alkyl halide: Type of nucleophile: Solvent: Is the product racemic?
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