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

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

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions

Section19.SE: Something Extra

Problem 28VC

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4. A CHEM 245 student wants to synthesize some ethylene glycol to use as antifreeze in his radiator this winter. He proposes the following reaction to his instructor, who quickly explains that this reaction won't work as proposed due to the student's choice of reagent. 1) NaH 2) H20 OH Но a) Why can't sodium hydride (NaH) be used as the nucleophile in the reaction above? b) Propose an alternate reagent that COULD be used with the ethylene oxide to successfully give the desired ethylene glycol product.
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 organic product you would expect to isolate from the nucleophilic substitution reaction between the molecules shown. Note: You do not need to draw any of the side products of the reaction, only the substitution product. D xx + H₂O + X Click and drag to start drawing a structure.
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Ketones and aldehydes react with sodium acetylide (the sodium salt of acetylene) to give alcohols, as shown in the following example: R OH 1. HC=C: Na* 2. H30* R2 Rí `R2 HC Draw the structure of the major reaction product when the following compound reacts with sodium acetylide, assuming that the reaction takes preferentially from the Re face of the carbonyl group. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • You do not have to explicitly draw H atoms. • If a group is achiral, do not use wedged or hashed bonds on it. H H3C H CH3
1. Predict the product and provide the mechanism for the following reversible nucleophilic addition. NaOH in H₂O 2. Predict the product and provide the mechanism for the following reversible nucleophilic addition. H2SO4 (cat) H EtOH
Substitution Reactions Predicting the product of a nucleophilic substitution reaction Draw the organic product you would expect to isolate from the nucleophilic substitution reaction between the molecules shown. Note: You do not need to draw any of the side products of the reaction, only the substitution product. HO + + Br xx X S C Click and drag to start drawing a structure.
Draw the organic product you would expect to isolate from the nucleophilic substitution reaction between the molecules shown. Note: You do not need to draw any of the side products of the reaction, only the substitution product. H × 5 Br + HO + 1 Click and drag to start drawing a structure.
1c. What is the nucleophile in the following reaction? .Br CH;CO0 Na LO OCCH3 NaBr ld. What is the electrophile in the following reaction? Br CH;COO Na L0OCCH3 NaBr +
Suggest a step by step mechanism for this reaction.
Do not give handwriting solution.