Determine the major product of the following reaction. For basic nucleophiles, you can assume there was a follow-up protonation step to create the alcohol functional group. You can ignore stereochemistry for this assignment. 3) 1) Br2, H₂O 2) NaOH : Br-Mg.
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- 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…3) Any compound or ion with at least one lone pair can be considered a base and/or a nucleophile. The relative basicity and nucleophilicity of the species is one of the most important factors that determine the mechanism of a reaction on sp³-carbon atoms. Please show an example of a) a reagent that is a strong nucleophile and a strong base, b) a reagent that is a weak nucleophile and a strong base, c) a reagent that is a strong nucleophile and a weak base, d) a reagent that is a weak nucleophile and a weak base. Which nitrogen atom in the structure below is most nucleophilic? Please explain by discussing the electron density around each nitrogen atom. Show at least three resonance structures of the compound. N.1. Predict the product, and propose a mechanism for the following nucleophilic addition to aldehyde or ketone. Are the products different from one another? Why do the reactions proceed via different mechanisms? Note the charges on the intermediates of acid and base catalyzed reactions. Oxygen nucleophile in acidic condition H2O, [H+] Oxygen nucleophile in basic condition NaOH
- Under acid-catalyzed conditions, epoxides can be opened by a variety of nucleophiles other than water, such as alcohols. In such a case, the nucleophile will generally attack at the more substituted position. Using this information, predict the products for each of the following reactions (a-b): ? 1) RCO-H 2) [H₂SOJ Modify the given structure to draw the major product(s). Use the single bond tool to interconvert between double and single bonds. If a racemic mixture of enantiomers is expected, draw both enantiomers. Note: you can select a structure and use Copy and Paste to save drawing time. CH₂ Edit Drawing A6) Write the mechanism (two propagation steps only, starting with the bromine radical in the first step and using Br2 in the second step) and that would explain how the following two products are produced. (Hint – the allylic radical is resonance stabilized.) Br Br NBSorgo chem questions
- 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 • You do not have to consider stereochemistry. • Include all valence lone pairs in your answer. OH • Do not include counter-ions, e.g., Na+, I¯, in your answer. • In cases where there is more than one answer, just draw one.The question is: "Draw the curved arrow mechanism for the reaction between pentan-2-one and (CH3)3O– in t-butanol to form an enolate. Draw all electrons and charges on both resonance structures. Then answer the question about the reaction." I got the initial arrows correct, but am not entirely sure what the carbanion intermediate would look like and then what the curved arrows would be to convert it to its final oxanion formFor 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
- 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. CH3OH H3C CI • • • • 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.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 [FМЕСНANISMS 1,2-epoxy-1-methylcyclopentane undergoes both acid-catalyzed and base-catalyzed opening of the epoxide ring to form two different products. > Using ethanol as the solvent and an appropriate acid, show the steps in the acid catalyzed mechanism, writing structures for all products of the steps. Circle the major product(s). > Using ethanol as the solvent and an appropriate base, show the steps in the base- catalyzed mechanism, writing structures for all products of the steps. Circle the major product(s). 1,2-epoxy-1-methylcyclopentane CH3



