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A naturally occuring antibiotic called m...

A naturally occuring antibiotic called mycomycin `(A)` has the structure as shown below.
`Hoverset(13)(C)-=overset(12)(C)-overset(11)(C)-=overset (10)(C)H-overset(9)(C)H=overset(8)(C)=overset(7)(C)H(overset(6)overset(4)(C)H=overset(5)overset(3)(C)H)_(2)-overset(2)(C)H_(2)overset(1)(C)OOH(A)`
Which statement is correct ?
Stereochemistry at `C-10` and `C-12`, when compound `(A)` is hydrogenated with Lindlar's catalyst and Birch Reduction , rescpectively, is

A

`10E` and `12E` in both cases

B

(10Z,12Z) and (10E,12E), respectively

C

`(10E,12E)` and `(10Z, 12 Z )`, respectively

D

`10Z` and `12Z` in both cases

Text Solution

AI Generated Solution

The correct Answer is:
To solve the question regarding the stereochemistry of mycomycin (A) at C-10 and C-12 when subjected to hydrogenation with Lindlar's catalyst and Birch reduction, we can follow these steps: ### Step 1: Understand the Reactions - **Lindlar's Catalyst**: This catalyst is used to hydrogenate alkynes to cis-alkenes (Z configuration). It selectively adds hydrogen to the double bonds without fully saturating the compound. - **Birch Reduction**: This reaction involves the reduction of alkynes to trans-alkenes (E configuration) using sodium in liquid ammonia and ethanol. ### Step 2: Analyze the Structure of Mycomycin (A) - Identify the positions of the double bonds in mycomycin (A). The relevant positions for this question are C-10 and C-12. - Determine the stereochemistry at these positions before and after the reactions. ### Step 3: Apply Lindlar's Catalyst - When mycomycin (A) is treated with Lindlar's catalyst, the double bonds at C-10 and C-12 will be converted to cis-alkenes. Thus, the stereochemistry at these positions will be: - C-10: Z configuration - C-12: Z configuration ### Step 4: Apply Birch Reduction - When mycomycin (A) undergoes Birch reduction, the double bonds at C-10 and C-12 will be converted to trans-alkenes. Thus, the stereochemistry at these positions will be: - C-10: E configuration - C-12: E configuration ### Step 5: Conclusion - Therefore, the stereochemistry at C-10 and C-12 after hydrogenation with Lindlar's catalyst will be 10Z and 12Z, respectively. - After Birch reduction, the stereochemistry will be 10E and 12E, respectively. ### Final Answer The correct statement is that the stereochemistry at C-10 and C-12 when compound (A) is hydrogenated with Lindlar's catalyst and Birch reduction, respectively, is: - **C-10: Z, C-12: Z (from Lindlar's catalyst)** - **C-10: E, C-12: E (from Birch reduction)**

To solve the question regarding the stereochemistry of mycomycin (A) at C-10 and C-12 when subjected to hydrogenation with Lindlar's catalyst and Birch reduction, we can follow these steps: ### Step 1: Understand the Reactions - **Lindlar's Catalyst**: This catalyst is used to hydrogenate alkynes to cis-alkenes (Z configuration). It selectively adds hydrogen to the double bonds without fully saturating the compound. - **Birch Reduction**: This reaction involves the reduction of alkynes to trans-alkenes (E configuration) using sodium in liquid ammonia and ethanol. ### Step 2: Analyze the Structure of Mycomycin (A) - Identify the positions of the double bonds in mycomycin (A). The relevant positions for this question are C-10 and C-12. ...
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