# Does RedP+HI reduce all carbon functional groups to alkane? Tags: organic-chemistry, organic-reduction - Score: 19 - Views: 25129 - Answers: 1 - Answered: yes - Asked by: Gaurang Tandon (10193 rep) - Asked: 2018-02-15 - Edited: 2018-03-17 - Site: chemistry ## Question I've seen the related questions 1 and 2, they're not duplicates So. when introducing Red P+HI reduction, our teacher said that it is the strongest reducing agent, and it can reduce any functional group i.e. all of these: carboxylic acid, acid anhydride, ether, amide, acid halide, carbonyl, and nitrile However, today I stumbled upon a question in my book involving a step in the synthesis of ibuprofen, where they did not reduce the carboxylic acid group even after using RedP+HI. I searched a lot on the internet, and finally came across this paper which confirms this: paper - notice they've only reduced the alcohol in step (ii) This now makes me wonder if what I was taught is actually correct. Which brings me to the question: Does RedP+HI really reduce all carbon functional groups to alkane? ## Answers ### Answer by Outlander (score: 10) Nope, in general it doesn't. You are correct. See also for example: