This is a question from an o-chem study guide. Can you help me understand why some reactions only give the meso product as well as help me understand how this reaction works? Which of the follawing reaction sequences will give the meso product?H DDHmeso only1) D, Pd Caco, Phco,, quinaline EOH21 Na. NH, (lia), EICHI) NANH, NH, THE21 D, Pd-C, PESO, quinoline1) Na, NH, (ligl, t-BuOH21 H3, Pd-C, PECO, quinoline ELOHD,, Pd Caco, Phco, quinoline EtOH21 H,, Pd Caco, EIOH

Answered: H D DH meso only 1| D, Pa Caco, Phco,,…

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Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

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This is a question from an o-chem study guide. Can you help me understand why some reactions only give the meso product as well as help me understand how this reaction works?

Which of the follawing reaction sequences will give the meso product?
H D
DH
meso only
1) D, Pd Caco, Phco,, quinaline EOH
21 Na. NH, (lia), EICH
I) NANH, NH, THE
21 D, Pd-C, PESO, quinoline
1) Na, NH, (ligl, t-BuOH
21 H3, Pd-C, PECO, quinoline ELOH
D,, Pd Caco, Phco, quinoline EtOH
21 H,, Pd Caco, EIOH

Expert Solution

Step 1

1 . Lindlar catalyst - heterogeneous catalyst comprising of Pd deposited on Calcium carbonate or barium sulfate , poisoned with various form of lead or sulfur and quinoline . It is used in hydrogenation of alkynes to alkenes . It always gives cis alkene .

2. Na/NH ₃- This catalyst reduces the alkyne into trans alkene .

3. H ₂/Pd-C - reduce alkene / alkyne to alkane .

Meso compound - these are non optically active compounds despite of having chiral centers because their mirror images are superimposable .

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