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23 June, 08:15

1a) consider the mixed aldol condensation reaction of 1-methylcyclopentane-1-carbaldehyde (shown below) and 3,3-dimethyl-2-butanone (shown below) in the presence of sodium hydroxide. provide the expected major mixed aldol condensation product for this reaction (can exist as e or z isomer so you can draw either)

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  1. 23 June, 11:07
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    Aldehydes and ketones having α-hydrogen atoms, undergoes aldol condensation, in present of base (NaOH).

    The initial product formed during this reaction is β-hydroxy alcohol, which then undergoes dehydration to form α,β-unsaturated aldehyde or ketone.

    In present case, 3,3-dimethyl-2-butanone has 2α-hyrogen atom, while methylcyclopentane-1-carbaldehyde has 1α-hydrogen atom. So the major product formed during cross aldol condensation reaction of these reactants is:

    5-hydroxy-4,4-dimethly-1 - (2-methylcyclopentyl) pent-1-en-3-one.

    The complete reaction product formed is shown below.
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