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4.19: Extra Problems with Nucleophilic Substitution and Elimination

  • Page ID
    200815
  • Exercise \(\PageIndex{1}\)

    Fill in the missing items in the following synthesis. Includes: aliphatic nucleophilic substitution, carboxylic substitution, enolates, addition to carbonyl (anionic nucleophiles).

    NScassiolq.png

    Exercise \(\PageIndex{2}\)

    Fill in the missing items in the following synthesis. Includes: addition to carbonyls (anionic nucleophiles, neutral nucleophiles, aliphatic nucleophilic substitution, Mitsunobu reaction).

    auriantoclavineEllman2010.png

    Exercise \(\PageIndex{3}\)

    Fill in the missing items in the following synthesis. Includes: aliphatic nucleophilic substitution,sulfonate substitution, Mitsunobu reaction, silyl ether cleavage, nucleophilic substitution of epoxides, elimination / dehydration.

    lepistineFukuyama2014.png

    Exercise \(\PageIndex{4}\)

    Fill in the missing items in the following synthesis. Includes: addition to carbonyls (ylides), nucleophilic substitution of epoxides, carboxylic substitution.

    Argentilactone.png

    Exercise \(\PageIndex{5}\)

    Fill in the missing items in the following synthesis. Includes: aliphatic nucleophilic substitution, carboxylic substitution, sulfonate substitution, addition to nitriles, addition to carbonyls (ylides).

    dolabellatrienone.png

    Exercise \(\PageIndex{6}\)

    Fill in the missing items in the following synthesis. Includes: aliphatic nucleophilic substitution, carbonyl addition (anionic nucleophiles, acetals, ylides), carboxylic substitution, silyl ethers.

    dinemasone.png

    Exercise \(\PageIndex{7}\)

    Fill in the missing items in the following synthesis. Includes: aliphatic nucleophilic substitution, sulfonate substitution, elimination.

    janoxepinTaylor2012.png

    Exercise \(\PageIndex{8}\)

    Predict products of the following reactions.

    SNEStarburst1.png

    Exercise \(\PageIndex{9}\)

    Predict products of the following reactions.

    SNEStarburst2.png

    Exercise \(\PageIndex{10}\)

    Predict products of the following reactions.

    SNEStarburst3.png

    Exercise \(\PageIndex{11}\)

    Predict products of the following reactions.

    SNEStarburst4.png

    Exercise \(\PageIndex{12}\)

    Predict products of the following reactions.

    SNEStarburst5.png

    Exercise \(\PageIndex{13}\)

    Predict products of the following reactions.

    SNEStarburst6.png