Question

(31 pts) Provide the reaction product(s), and indicate the type of reactions ( S1, S2, E1 and En and antical activity (Yes or No) in the round rectangles, respectively. If reaction does not take place indicate "No Reaction in the box Draw 2 major products Reaction type Draw 1 minor product Reaction type Is the product optically active? Draw 1 product Reaction type CH,OH NaCN acetone Is the product optically active? arrier Draw 1 product Reaction type secondary alkyl-bromide LDA isopropyl amine NaOCOCH DMF Draw 1 product Reaction type NaOCH CH,OH Draw 1 MAJOR product Draw 1 MINOR product Reaction type Reaction type

Answer 1

The answer to the given question is as follows:

• CH₃OH (Methanol) is a poor nucleophile, thus will favour S_N1 reaction at secondary carbon center and the product will be optically active with retension of configuration.
• NaCN is strong nucleophile, thus will favour E2 elimination and product will be optically inactive.
• LDA is hindered strong nucleophile thus will favour E2 elimination.
• Acetate ion is weak nucleophile thus will give SN₁ reaction.
• Methoxide ion is a strong base thus, will favour E2 elimination and give major product and SN₂ route will give the minnor product with inversion of configuration.
  O 0 Bn Н > Minnor major HO (Major) Optically active Brown - 88-8 - Ει (Minnor)
  
  Nacno acetone, NON strongly basic, unhindered nucleophile, and reactant is secondary ("xx" type, where x = leaving group. Ę will be more favourable over SN, SN,. Optically inactive
  
  Xill Br LOA Isopropyl amine LOA- lithium voličso propyl vamine & it is an hindered strong nucleophile . Ez is more favourable over SN, SN, rand & reaction.
  
  Z11Br Ona gococks 2.11gc-cts I DMA sus casto cacetate con) cs a poom nucleophile. Thus, it will sNI reaction as it is nucleophilic enough to react with 7- carbocation generated in the reaction in an aprotic solvent bMF. Biliran DMF
  
  Geome XIBM + na gocthy CIGOH Go Mismor major → Methoxide (Cze) cs a very strong unhindered nudeophile. Thus, will prefer Ez over SN2 < oct Major Z poc 8 Another possibility giving crinmor product. ZB och socks SNg Amversion of configuration minnon