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Bookmarks People Mastering chemistry Chapter 19 homework Secure https llsession. 1642016&offset; next signed in as Suhail Kathari Problem 19.3 5 of 16 Problem 19.3 Part A Why is the conjugate acid of morpholne more acidic than the coniugate acid of piperidine? The oxygen in morpholne does not wrhdraw electrons inductively, which make protonated morpholine the stronger acd. The sp 2 oxygen in morphoina is lesseectronegative than the sp 2 carbon af piperidine, which make psotonatod morpholino the stronger acid. The oxygen in morpholine wthdraws electons inductively, which make protonated morphoine the stronger acid. The sp 2 oxygen in morpholine is more electronegative than the sp 2 carbon of piperidine, which make protonated morpholne the stronger adid Submit My Answers give ue Continue

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Ans 19.3 Part A . option C. The oxygen in morpholine withdraws electron inductively, which make protonated morpholine the stronger acid.

The carbon of piperidine is sp3 hybridised and not sp2, and the lone pair of nitrogen atom resides in sp3 orbital having 25% S character.

The protonated form of morpholine also known as morpholinium, has an electronegative oxygen in the ring that withdraws the electrons inductively reducing the electron density at nitrogen , due to which it can lose its proton with ease making it a stronger acid.

The conjugate acid of piperidine even lacks oxygen atom in its ring so it is a weak conjugate acid.

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