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When (R)-4-bromohept-2-yne is treated with H2 in the

Chapter 10, Problem 10.47

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QUESTION:

When (R)-4-bromohept-2-yne is treated with H2 in the presence of Pt, the product is optically inactive. Yet, when (R)-4-bromohex- 2-yne is treated with the same conditions, the product is optically active. Explain.

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QUESTION:

When (R)-4-bromohept-2-yne is treated with H2 in the presence of Pt, the product is optically inactive. Yet, when (R)-4-bromohex- 2-yne is treated with the same conditions, the product is optically active. Explain.

ANSWER:

Step 1 of 2

When the alkyne of (R)-4-bromo-2-heptyne is fully hydrogenated, there will be two equivalent propyl groups attached to the chiral center, rendering it achiral.

     

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