2. The oxetane ring is a four sided ring with 3 carbons and 1 oxygen. The oxetane ring is found in Taxol, which is a natural product that is used as a cancer drug. Oxetanes are used in medicinal chemistry. Compound A is an oxetane. Br Br- H2SO4 CH3MGBR 2 possible intermediates HO- A В a. (i) One carbon in Compound A is an alpha carbon and a beta carbon. Circle this carbon. (NOTE: two carbons are alpha and beta carbons.) (ii) Box the leaving group(s) in Compound A. If a leaving group is poor, how can it be made better? b. Compound A reacts with H2SO4. Draw two possible intermediates of this reaction. Which intermediate most likely forms? Give reasons. c. One of your intermediates from part b reacts with a nucleophile to form several possible products. Compound B is one possible product. What nucleophile reacts with the intermediate to form Compound B? Use curved arrows to show how Compound B is produced from this intermediate and nucleophile.
2. The oxetane ring is a four sided ring with 3 carbons and 1 oxygen. The oxetane ring is found in Taxol, which is a natural product that is used as a cancer drug. Oxetanes are used in medicinal chemistry. Compound A is an oxetane. Br Br- H2SO4 CH3MGBR 2 possible intermediates HO- A В a. (i) One carbon in Compound A is an alpha carbon and a beta carbon. Circle this carbon. (NOTE: two carbons are alpha and beta carbons.) (ii) Box the leaving group(s) in Compound A. If a leaving group is poor, how can it be made better? b. Compound A reacts with H2SO4. Draw two possible intermediates of this reaction. Which intermediate most likely forms? Give reasons. c. One of your intermediates from part b reacts with a nucleophile to form several possible products. Compound B is one possible product. What nucleophile reacts with the intermediate to form Compound B? Use curved arrows to show how Compound B is produced from this intermediate and nucleophile.
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Chapter24: Polymer Materials: Synthetic And Biological
Section: Chapter Questions
Problem 24.76QP
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Question
6
Transcribed Image Text:2. The oxetane ring is a four sided ring with 3 carbons and 1 oxygen. The oxetane ring is found in Taxol, which is a natural
product that is used as a cancer drug. Oxetanes are used in medicinal chemistry. Compound A is an oxetane.
Br
Br-
H2SO4
CH3MGBR
2 possible
intermediates
HO-
A
В
C
a. (i) One carbon in Compound A is an alpha carbon and a beta carbon. Circle this carbon. (NOTE: two carbons are alpha
and beta carbons.)
(ii) Box the leaving group(s) in Compound A. If a leaving group is poor, how can it be made better?
b. Compound A reacts with H2SO4. Draw two possible intermediates of this reaction. Which intermediate most likely
forms? Give reasons.
c. One of your intermediates from part b reacts with a nucleophile to form several possible products. Compound B is one
possible product. What nucleophile reacts with the intermediate to form Compound B? Use curved arrows to show how
Compound B is produced from this intermediate and nucleophile.
d. Compound B reacts with CH,MgBr to form three possible products. Compound C is one possible product. Use curved
arrows to show how Compound C forms from Compound B.
e. (i) One of your intermediates from part b reacts with a nucleophile to form several possible products. Draw the structure
of another possible product besides Compound B.
(ii) Compound B reacts with CH,MgBr to form three possible products. Draw the structure of another possible product
besides Compound C.
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