MS 920 - Aldehydes and Ketones

MS 920 - Aldehydes and Ketones

Textbook and Chapter: Carey and Giuliano 8th Ed. (2010), Chapter 17

Keywords: aldehydes, ketones

Description: Problems related to aldehydes and ketones: Wittig, imines, acetals, and protecting groups.

Total Problems: 6

  1. Problem # 710

    Rank the carbonyls A-D below in order of decreasing electrophilicity (reactivity with nucleophiles).

    (1 = Most reactive).  Explain your reasoning.

  2. Problem # 711

    Show two ways of preparing the alkene below via the Wittig reaction starting from triphenyl phosphine (PPh3).

    Is one route better than the other? Why?

  3. Problem # 712

    Show what combination of amine and carbonyl would result in each imine or enamine.

  4. Problem # 713

    When a carbonyl is treated with semicarbazide under acidic conditions an "imine" is produced called a semicarbazone.

    Which of the two products below is the correct structure for a semicarbazone? Explain.

  5. Problem # 714

    Complete each synthesis below. All carbon sources must come from alkenes.

    Each synthesis will involve protecting groups.

  6. Problem # 715

    α-D-glucose is shown below.

    a) Is α-D-glucose an acetal, hemiacetal, ketal, or hemiketal?

    b) Draw the carbonyl form of α-D-glucose.