Carey and Giuliano 8th Ed. (2010)
CH 10: Conjugation in Alkadienes and Allylic Systems

Solutions can be seen at mendelset.com/chapters/274


  1. Problem # 522

    Let's work through a 1,2 and 1,4 addition. Draw the structures for each of the species in the six boxes below. Also draw curved arrows to show electron movement. 

  2. Problem # 528

    Indicate which of the molecules below are chiral (if any).

  3. Problem # 569

    Draw all resonance forms for each species. 

    For the anion and cation species, used curved arrows. For the radical species, use hooks.

  4. Problem # 570

    Rank the following dienes in order of decreasing reactivity with a dienophile in a Diels-Alder reaction. (1 = most reactive).

  5. Problem # 571

    Write the structure of the major organic product of each reaction.

  6. Problem # 572

    Let's work through a conjugate addition problem.

    Write out the mechnanism for the formation of the 1,2 and 1,4 products of the reaction below.

  7. Problem # 574

    Predict the product for each Diels-Alder reaction. Indicate stereochemistry where appropriate.

  8. Problem # 575

    Predict the product for each Diels-Alder reaction. Indicate stereochemistry where appropriate.

  9. Problem # 576

    Retro Diels-Alder: show a combination of diene and dienophile that would result in each Diels-Alder adduct.

  10. Problem # 577

    Retro Diels-Alder: show a combination of diene and dienophile that would result in each Diels-Alder adduct.

  11. Problem # 1281

    Allylic and benzylic halides tend to undergo both SN1 and SN2 substitution reactions at a faster rate than their alkyl counterparts.

    For example, both allyl chloride and benzyl chloride undergo SN2 reaction at a faster rate than propyl chloride. 

    The same holds true for SN1 reactions: a 2° allyl or benzyl halide undergoes SN1 reaction faster than a 2° alkyl halide. Explain.