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- 7. Circle the best substrate for a nucleophilic substitution reaction. OH OCH3 SH CIDraw the mechanism for the reaction of an alkyl halide with sodium azide followed by reduction. Complete the mechanism of the initial step of the reaction, then identify the key intermediate and the product. Step 1: Draw curved arrows. o z + Na + || : z: I Step 2: Complete the intermediate. Na +CHEM 372-Problem Set 13 - Ester and amide hydrolysis 4. Esters undergo hydrolysis to the corresponding alcohol and carboxylate: ethyl acetate is hydrolyzed to ethanol and acetate. However, amides are surprisingly stable under strong base. Draw the first intermediate in the hydrolysis of the amide. Is a good leaving group present? Continue with the prove to yourself that the basic hydrolysis of an amide is more difficult than ester mechanism and hydrolysis. NaOH H3C CH3 H3C OH Na CH3 heat NaOH H3C CH3 heat
- This reaction is an example of conjugate addition of a nucleophile to an a,ẞ-unsaturated carbonyl. O CH3CH2CH2CH=CHCSCOA H₂O OH CH3CH2CH2CHCH2CSCOA Draw the two resonance structures of the enolate anion intermediate for this reaction. • Draw an R1 group in place of COA. The R group tool is located in the charges and lone pairs drop-down menu. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate resonance structures using the symbol from the drop-down menu. ->> 90-87 O + ? ChemDoodle >3. Show the mechanism for the following addition/substitution. cat. H2SO4 MeNH2 remove H₂O H H Why doesn't a primary amine need to add a second nucleophile? (i.e. why does it make an imine instead of an aminal?)3. Draw the most stable product. Is this a nucleophilic reaction or an acid base reaction? HANN H₂N CH3COOH
- Show a possible mechanism for the following reaction CN CO,Me CN.CN HO a-Determine if it will follow an SN1 or SN2 mechanism and state which it will follow. b-Explain the reasoning for the mechanism choice, including analysis of the alkyl halide, nucleophile and solvent. c-Draw the mechanism the reaction will follow.Which best explains the following reaction. OH OH H3O+ This reaction does not work because the major product would be an alkene formed by elimination. This reaction does not work because the major product would be an ester. This reaction does not work because three ethers can be formed. This reaction works and the only ether product formed is shown. +
- 1. Predict the product and provide the mechanism for the following reversible nucleophilic addition. bbs off O.H So NaOH in H₂O5. Glutaraldehyde is a germicidal agent that is sometimes used to sterilize medical equipment. In mildly acidic conditions, glutaraldehyde exists in a cylic form as shown below. Draw a stepwise detailed reaction mechanism for the reaction below. Но OH [H,o*) H. GlutaraldehydeThis reaction is an example of conjugate addition of a nucleophile to an a,ß-unsaturated carbonyl. CНз CHз Нао ОН Draw the two resonance structures of the enolate anion intermediate for this reaction.