5. Each of the following target molecules can be prepared via an intramo- lecular Diels-Alder reaction. Determine the required disconnection/ retrosynthesis for each, paying close attention to the stereochemistry of the TM. A CH₂O CH₂O с CO₂Me AIA CO₂Me CO Me CO₂Me

Please draw the most important resonance structure of the cationic intermediate leading to the MAJOR product of electrophilic bromination of this compound

Predict the order of reactivity (1 being the slowest, 3 being the fastest) of primary, secondary, and tertiary alkyl halides toward nucleophilic displacement by an SN1 reaction mechanism

11) The SN2 reaction of iodocyclopropane with sodium methylmercaptide (CH3SNA) is not observed. Why? X- H + CH3SNA + Nal SCH3 A) iodide, generally, is not a good leaving group B) the cyclopropane ring sterically hinders the reaction pathway C) sulfur anions, generally, are not good nucleophiles D) the required hybridization change at the transition state causes too much strain E) the sulfur anion is too large

Which of the following is the best nucleophile in an SN2 reaction? Group of answer choices H2O (CH3)3CO- CH3O- CH3OH

Determine the mechanism of nucleophilic substitution of attached reactionand draw the products, including stereochemistry.

Schlapbach and Hoffmann used a stereoelectronic effect to control the stereochemistry of the reaction below. Draw the structure of the transition states for competing reactions to explain the origin of stereoselectivity. lag X = CI, OR, N(Me)SO₂R R H + Me R OH Me X

Identify whether the following mechanism is SN1, SN2, E1, E2, or E1cB or a combination. a. b. C. d. Br benzyl bromide Br benzyl bromide NaOEt in dry alcohol water in formic acid solution 3-iodocyclohexan-1-one 1-iodo-2,2-dimethylbutane NaOEt in EtOH Aa NaSCH3 OH E

The reaction of butan-2-ol with concentrated aqueous HBr goes with partial racemization, giving more inversion than retention of configuration. Propose a mechanism that accounts for racemization with excess inversion

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