Difference between Na,NH3 and a Lindlar Reduction for Synthesis in Organic Chemistry 1

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Difference between Na,NH3 and a Lindlar Reduction for Synthesis in Organic Chemistry 1

[From: ] [author: ] [Date: 11-12-13] [Hit: ]

What happens mechanistically with Na and NH3?Thank you in advance! (I know it is hard to ask in words and not pictoral examples, sorry!)-With Lindlars catalyst the two H atoms add from the metal surface in one step thereby giving the CIS isomer.Na / NH3 adds one H atom and then the second; the two step sequence gives the more energetically favorable TRANS isomer.......

On my test we went from an alkyne to an alkene using Na, NH3. For my answer, I used reagents/solvents for a lindlar reduction. I got partial credit.

When do I use Na with/ NH3 vs a lindlar reduction on synthesis problems? What happens mechanistically with Na and NH3?

Thank you in advance! (I know it is hard to ask in words and not pictoral examples, sorry!)

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With Lindlar's catalyst the two H atoms add from the metal surface in one step thereby giving the CIS isomer.
Na / NH3 adds one H atom and then the second; the two step sequence gives the more energetically favorable TRANS isomer.

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