Check to see if there is a strong nucleophile present

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and the nature of the leaving group. Check to see if there is a strong nucleophile present. Some of the SN1 material will be covered in lecture on Monday. CH 3 H 3 C LiN 3 DMF I H CH 3 OH H 3 C 1. 2. ClO 2 S CH 3 NaSCH 3 , DMF EtI DMF N e. O MeO O S O O H 3 C ClO 2 S CH 3 h. H OH H 3 C 1. 2. NaCN, DMF CH 3 NaO O CH 3 CH 3 OH i. Chem 33, Kanan & Stack, 2012, PS 7; pg 5
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NaN 3 CH 3 OH b. The SN2 reaction of 1-chloro-3-methylcyclopentane ( 0.1 M) with NaN 3 ( 0.1 M) proceeds faster if a small amount of NaI (0.001 M) is added to the reaction mixture, but a different diastereomeric product ( ( 1S,3S )-1-azido-3- methylcyclopentane) results as the major product. Provide a mechanistic postulate that accounts for the rate acceleration and product (hint: how much faster is I - as a nucleophile than N 3 - in methanol). 7. Consider the SN2 reaction of ( 1S,3S )-1-chloro-3-methylcyclopentane with NaN 3 in methanol. a. Clearly draw the product of this reaction and assign the absolute configuration at all stereogenic centers. CH 3 ( 1S,3S )-1-chloro-3-methylcyclopentane Cl CH 3 Cl CH 3 Cl CH 3 N 3 CH 3 N 3 c. If a large amount of iodide is added (1.0 M) rather than a catalytic amount, a mixture of the diastereomeric azide products results. Suggest a mechanistic reason. Δ G° ~ -20 kcal mol -1 NaI, NaN 3 CH 3 OH Chem 33, Kanan & Stack, 2012, PS 7; pg 6
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