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Draw the organic products formed when cyclopentene is treated with each reagent. With

Chapter 12, Problem 12.39

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QUESTION:

Draw the organic products formed when cyclopentene is treated with each reagent. With some reagents, no reaction occurs.

a. \(\mathrm{H}_{2}+\mathrm{Pd}-\mathrm{C}\)

b. \(\mathrm{H}_{2}+\text { Lindlar catalyst }\)

c. \(\mathrm{Na}, \mathrm{NH}_{3}\)

d. \(\mathrm{CH}_{3} \mathrm{CO}_{3} \mathrm{H}\)

e. \(\text { [1] } \mathrm{CH}_{3} \mathrm{CO}_{3} \mathrm{H} \text {; [2] } \mathrm{H}_{2} \mathrm{O}, \mathrm{HO}^{-}\)

f. \(\text { [1] } \mathrm{OsO}_{4}+\mathrm{NMO} ; \text { [2] } \mathrm{NaHSO}_{3}, \mathrm{H}_{2} \mathrm{O}\)

g. \(\text { [1] } \mathrm{OsO}_{4}+\mathrm{NMO} ;[2] \mathrm{NaHSO}_{3}, \mathrm{H}_{2} \mathrm{O}\)

h. \(\text { [1] } \mathrm{LiAlH}_{4} \text {; [2] } \mathrm{H}_{2} \mathrm{O}\)

i. \(\text { [1] } \mathrm{O}_{3} \text {; [2] } \mathrm{CH}_{3} \mathrm{SCH}_{3}\)

j. \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COOH} \text {, Ti }\left[\mathrm{OCH}\left(\mathrm{CH}_{3}\right)_{2}\right]_{4},(-)-\mathrm{DET}\)

k. \(\text { mCPBA }\)

l. \(\text { Product in (k); then [1] } \mathrm{LiAlH}_{4} ; \text { [2] } \mathrm{H}_{2} \mathrm{O}\)

Questions & Answers

QUESTION:

Draw the organic products formed when cyclopentene is treated with each reagent. With some reagents, no reaction occurs.

a. \(\mathrm{H}_{2}+\mathrm{Pd}-\mathrm{C}\)

b. \(\mathrm{H}_{2}+\text { Lindlar catalyst }\)

c. \(\mathrm{Na}, \mathrm{NH}_{3}\)

d. \(\mathrm{CH}_{3} \mathrm{CO}_{3} \mathrm{H}\)

e. \(\text { [1] } \mathrm{CH}_{3} \mathrm{CO}_{3} \mathrm{H} \text {; [2] } \mathrm{H}_{2} \mathrm{O}, \mathrm{HO}^{-}\)

f. \(\text { [1] } \mathrm{OsO}_{4}+\mathrm{NMO} ; \text { [2] } \mathrm{NaHSO}_{3}, \mathrm{H}_{2} \mathrm{O}\)

g. \(\text { [1] } \mathrm{OsO}_{4}+\mathrm{NMO} ;[2] \mathrm{NaHSO}_{3}, \mathrm{H}_{2} \mathrm{O}\)

h. \(\text { [1] } \mathrm{LiAlH}_{4} \text {; [2] } \mathrm{H}_{2} \mathrm{O}\)

i. \(\text { [1] } \mathrm{O}_{3} \text {; [2] } \mathrm{CH}_{3} \mathrm{SCH}_{3}\)

j. \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COOH} \text {, Ti }\left[\mathrm{OCH}\left(\mathrm{CH}_{3}\right)_{2}\right]_{4},(-)-\mathrm{DET}\)

k. \(\text { mCPBA }\)

l. \(\text { Product in (k); then [1] } \mathrm{LiAlH}_{4} ; \text { [2] } \mathrm{H}_{2} \mathrm{O}\)

ANSWER:

Step 1 of 13

We need to draw the organic product formed when cyclopentene reacts with each of the given compounds.

Cyclopentene

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