Create your own SN1 reaction and label the steps 1) heterolysis of leaving group 2) coordination of nucleophile 3) Proton transfer

A student proposes the following reaction mechanism for the reaction in Model 6. Which step inthis mechanism is least favorable? Explain your reasoning.

Which of the following is a substitution reaction? “人一X II. スーズ I. 00 OH "メー人 IV. III. Br 人ー人 SH 1) 1 2) 11 3) l1 4) IV

e 2. Draw the structures and explain why CH3CH₂O and CH3CO₂ are good nucleophiles but CH3SO3, water, and alcohols (R-OH) are poor nucleophiles. Propose a 'cutoff for the amount of negative charge needed to be a good nucleophile. CH3CH₂O CH3CO₂ CH3SO3 H₂O CH3OH

29) Draw all of the expected products for the following reaction. Circle the most dominant product in each reaction. 'BUOK 3 NaOEt

Draw the product and the complete nucleophilic substitution mechanism (all curved arrows) for the reaction below. Use a hydride as a simple nucleophile. Do not show the Aluminum or lithium complex. LIAIH4

with the corresponding reaction step. Drag and drop options on the right-hand side to swap positions and match with items on the left. Reordering may cause items on the right- hand side to swap positions. A) B) C) D) Loss of leaving group Proton transfer (acid/ base) Nucleophilic attack Rearrangement OH H. A) OH Br Pr Br Et NaBr/H2SO4 Me + HSO4 Na Pri or Me Et Me Et Br Pr © D) Br Η ΘΗ Н B) c) H -H +0==0 OH H + H₂O III III III III

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 >

For the reaction sequence below, provide the correct reagents, intermediate or final product. Br You? Na enant.

3. Provide the mechanism for the following reversible nucleophilic addition. Show all curved arrows and intermediates. cat. H+ H₂O HO OH H H 1) protonate to activate 2) nucl adds 3) deprotonate what stays