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Chapter 12: PROBLEM 12.13 (page 466)

Question: A chiral alkyne A with molecular formula C6H10 is reduced with and Lindlar catalyst to B having the R configuration at its stereogeniccentre. What are the structures of A and B?

Short Answer

Expert verified

Answer

Structure A

Structure B

Step by step solution

01

Stereogenic center

An atom is attached with four different groups such that its mirror image non-superimposable is known as a stereogenic center.

When any two group鈥檚 positions are exchanged, the molecule structure results in enantiomers (two isomers with R and S configuration).

02

Reaction of A with Lindlar catalyst

The triple bond is reduced to a double bond (cis alkene).

Reduction of alkyne to an alkene with stereogenic carbon center

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Most popular questions from this chapter

Question: Draw the products formed when each naturally occurring compound is treated with O3followed by Zn,H2O.

Question: What allylic alcohol and DET isomer are needed to make each chiral epoxide using a sharpless asymmetric epoxidation reaction?

Question: Draw a stepwise mechanism for the following reaction.

Question: It is sometimes necessary to isomerize a cis alkene to a trans alkene in a synthesis, a process that cannot be accomplished in a single step. Using the reactions that you have learned in Chapters 8鈥�12, devise a stepwise method to convert cis-but-2-ene to trans-but-2-ene.

Question: Hydrogenation of alkene A with D2 in the presence of Pd-C affords a single product B. Keeping this result in mind, what compound is formed when A is treated with each reagent:

(a) mCPBA; (b) Br2 , H2O followed by base? Explain these results.
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