(a) On the basis of the following data, identify unknowns A, found in fresh cream prior to...

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(a) On the basis of the following data, identify unknowns A, found in fresh cream prior to churning, and B, possessor of the characteristic yellow color and buttery odor of butter. 

A: MS: m/z (relative abundance) = 88(M*, weak), 45(100), and 43(80). 'H NMR: 8 = 1.36 (d, J = 7 Hz, 3 H), 2.18 (s, 3 H), 3.73 (broad s, 1 H), 4.22 (q, J = 7 Hz, 1 H) ppm. IR: ỹ = 1718 and 3430 cm. B: MS:

(b) What kind of reaction is the conversion of compound A into compound B? Does it make sense that this should take place in the churning of cream to make butter? Explain. 

(c) Outline laboratory syntheses of compounds A and B, starting only with compounds containing two carbons. 

(d) The UV spectrum of compound A has a λmax at 271 nm, whereas that of compound B has a λmax at 290 nm. (Extension of the latter absorption into the violet region of the visible spectrum is responsible for the yellow color of compound B.) Explain the difference in λmax.

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Organic Chemistry structure and function

ISBN: 978-1429204941

6th edition

Authors: K. Peter C. Vollhardt, Neil E. Schore

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