( a ) The synthesis shown below is unlikely to occur . Showing all structures and reaction mechanisms indicate what is wrong with this synthesis

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Please provide some help for this question on the synthesis of following product.

( a ) The synthesis shown below is unlikely to occur . Showing all structures and reactionmechanisms indicate what is wrong with this synthesis ?"BYCH 2CH 2NBShu , CCIACH 3CH 3( 6 ) Showing all necessary structures and mechanisms indicate why it is not possible to prepare aGrignard reagent from 4 – bromo – 1 – pentanol ?