CHM247 Tutorial #8 (slides can be accessed here)

From acetylene Retroactively break this C-C bond to reveal a ketone

4 carbon atoms in B Break this C-C bond – make a secondary alcohol from aldehyde (C) electrophillic carbon make this into a nucleophillic carbon nucleophlie – Grignard reagent

nucleophlie – Grignard reagent

2,4-dinitrophenyl hydrazine – reacts with ketones and aldehydes to make a red precipitate – Positive test  compound is either a ketone or aldehyde Tollens’ reagent – reacts with aldehydes to make a silver mirror – Negative test  compound is not an aldehyde Therefore – all this jazz is telling you the compound is a ketone Use trial and error to draw a chiral ketone with the formula C 6 H 12 O