Unformatted text preview: Massachusetts Institute of Technology 5.13, Fall 2006 Problem Set #8
Due: December 4, 2006, 12:00 PM
1. Propose a one-step synthesis for the following compounds using the
CO 2Et 2. Write the products for the following reactions. O a) CH 3 H2C NaOCH3
CH3OH, D O
b) 2. HC CH 3
O 3. Identify the intermediates A and B in the transformation below and show how
they are formed (mechanism).
O H CH3
excess NaOEt O KOtBu A
Et B -OH H2O H3 C
O 1 Massachusetts Institute of Technology 5.13, Fall 2006 4. Write reagents (a, b, c, d) where they have been omitted from the following
synthetic sequence. Each letter may correspond to one or more reaction steops.
This sequence is the beginning of a synthesis of germanicol, a naturally
Me Me H
HO Me Me H
O Me H3C Me H3 C O O O O
CH 3 H+, ethylene glycol O O b Me Me
O O c O
Me M e Me H
Me Me Me Me H
O 1. Li, NH3
O O H
Me M e 2 Me
O Me d O Me O O Massachusetts Institute of Technology 5.13, Fall 2006 5. Provide a mechanism for each of the following transformations.
NaOMe (1 eq.) O a) Ph M eOH
O Ph H
Me N N cat. H+ N O Me
Me 6. Provide a synthesis for each of the following products.
O O a) Me O
H Ph O
c) b) Me N
H Me MeO H EtOH OH starting materials 3 Me PrOH
OH Ph O O
Ph Me ...
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- Chemical reaction, English-language films, ethylene oxide, Ethylene glycol, Robinson annulation