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Chapter 22: Q74. (page 920)

Question. Rank the following compounds in order of increasing frequency of the C=O absorption in their IR spectra.

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01

Step-by-Step SolutionStep 1: IR Absorption

The compounds with active dipole moment would absorb IR radiation depending on the strength of the bond and the difference in the rotational and vibrational states.

02

Order of absorption

The presence of a bulky group as a substituent of the C=O linkage would lower the absorption.

The presence of an electron releasing group (ERG) would also reduce the absorption to a shorter frequency.

Cyclization would increase the strength of the C-O-C bond, making the compound absorb at a higher frequency.

Therefore, the increasing order of IR absorption based on increasing wavenumber is as follows:

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Most popular questions from this chapter

Question: With reference to the structures of acetylsalicylic acid (aspirin, Chapter 2 opening molecule) and acetaminophen (the active ingredient in Tylenol), explain why acetaminophen tablets can be stored in the medicine cabinet for years, but aspirin slowly decomposes over time.

What aldehyde or ketone is needed to prepare each alcohol by metal hydride reduction?

Draw the products formed when A or B is treated with each reagent. In some cases, no reaction occurs.

  1. NaBH4, CH3OH
  2. [1] LiAlH4 ; [2] H2O
  3. [1] CH3MgBr ; [2] H2O
  4. [1]C6H5Li ; [2] H2O
  5. Na2Cr2O7, H2SO4,H2O

Draw a stepwise mechanism for the following reaction. Your mechanism must show how both organic products are formed.

Draw the products formed when CH3COCH2CH2CH=CH2is treated with each reagent: (a)LiAlH4, then H2O ; (b) NaBH4in CH3OH ; (c) H2(1 equiv), Pd-C; (d)H2(excess), Pd-C; (e)NaBH4 (excess) inCH3OH ; (f) NaBD4in CH3OH
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