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    Acid Derivatives and Amide Properties

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    I need some help in answering these questions. Full explanations please!
    1. The correct order of reactivity of acid derivatives towards nucleophilic attack is:
    esters > acid anhydrides > amides
    amides > esters > anhydrides
    carboxylates > esters > amides
    anhydrides > esters > amides

    2. N-methylacetamide is an example of:
    a primary amine
    a secondary amide
    a tertiary amide
    an N,N- disubstituted amide

    3. Acids can be reduced to aldehyde by:
    treatment with LiAlH4
    conversion to acid chloride followed by treatment with LiAlH[OC(CH3)]3
    conversion to amide followed by treatment with NaBH4
    conversion to ester followed by treatment with LiAlH4

    4. Amides are less basic than amines because:
    the carbonyl group donates electrons by resonance
    the carbonyl group withdraws electrons by resonance
    the nitrogen does not have a lone pair of electrons
    the nitrogen carries a full positive charge

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    Solution Preview

    Question 1

    Tutorial Help: In order to answer this, we must understand the nature of an electrophile, that which gets attacked by a nucleophile. The more positive charge around the electrophile, the greater it will be attacked by a nucleophile. Amides, RCONHR, are highly stable structures. Like esters (RCOOR), they can be hydrolyzed in acidic or basic solution. On the other hand, acid anhydrides (RCOOOCR) are very reactive to nucleophiles. Remember, good leaving groups is what makes for a strong ...

    Solution Summary

    This in-depth solution contains full explanations on the bonding and structure of the aforementioned molecules to determine reactivities, structure classification, reduction mechanisms and basicity.