Question

Complete the following reactions and state the dominant mechanism

f. 2-chloro-2-methylpentane + CH:ONa CH3OH → mechanism: g. 1-chloro-3-methylpentane + NaCN mechanism: h. 3-chloro-3-methylpentane + DBN → mechanism:

Answer 1

- 3-chloro-3-methyl bentane + DBN → + DBN - m I es-elimination Bulky base 30 Alkyl chloride DBM is non nucleophilic bulky base so gives E2 elimination Reaction with 3° alkyl chloride. And the elemination of less hindered H occur. D ON 3) dis diazabicydo (4.3.0] non-s-ene. in Let B base hető best 6 more hindered . - lexshinderel 1 Mechanism for 22 elimination H2 a must be antiperiplaner to each other Transition state of E2 elimination

2-chloro-2-methylpentane + Cngona t +Cn₂8 y a СА 3° alkyl chloride 3° alkyl chloride gives elimination reaction with enz 8Na. the reaction occur via Ez elimination mechanism. Mechanismo och₂ -Con Product Transition state of P2 elimination 9 I-chloro-3 methyl pentane + Nach ra " So ra + NaCN - T- d'alkylchloride lo alkyl halide gives substitution product Via SN2 In SN Mechanism s coorelinated transition state Nach with Mechanism. form. Mechanisma Tears Product s-Coordinated Transition . State a SN2 mechanism .