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Chapter 12: Q43E (page 385)

Propose structures for compounds that meet the following descriptions:

  1. An optically active compound C5H10Owith an IR absorption at 1730 cm-1.
  2. A non-optically active compound C5H9N with an IR absorption at 2215cm-1.

Short Answer

Expert verified

All the absorptions seen in alkanes is due to the C-C and C-H bonds.The C-H bonds show absorption in the region 2850 to 2950 cm-1 and the C-C bonds are seen in the region 800 to 1300 cm-1.Most of the organic compounds exhibit these absorptions as they comprise saturated alkane portion.

Step by step solution

01

IR spectroscopy

All the absorptions seen in alkanes is due to the C-C and C-H bonds.The C-H bonds show absorption in the region 2850 to 2950 cm-1 and the C-C bonds are seen in the region 800 to 1300 cm-1.Most of the organic compounds exhibit these absorptions as they comprise saturated alkane portion.

02

Proposing the structure of the compound with different description

(a)The optically active compound with the formula C5H10O that absorbs at 1730 cm-1can be given as:

Optically active compound

The IR absorption at this region is due to the saturated aldehyde. The name of the compound is 2-methylbutanal.

(b)The non optically active compound has a formula C5H9N that absorbs at 2215 cm-1 can be given as:

The absorption at this frequency is due to the cyanide functional group. The given compound is trimethylacetonitrile.

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