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Chapter 12: Q 43 E (page 385)

Question: Propose structures for compounds that meet the following descriptions:

  1. An optically active compoundC5H10Owith an IR absorption at1730cm-1.

  2. A non-optically active compound C5H9N with an IR absorption at2215cm-1.

Short Answer

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a)

b)

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 to2950cm-1 and the C-C bonds are seen in the region 800 to1300cm-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 formulaC5H10O that absorbs at1730cm-1 can be given as:

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 at2215cm-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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Most popular questions from this chapter

Predict the products for the reactions in Problem 8-26 if each were run in DMSO with water. Show the complete mechanism including appropriate regiochemistry and stereochemistry.

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.

Question: By knowing the natural abundances of minor isotopes, it鈥檚 possible to

calculate the relative heights of and M+1 peaks. If 13C has a natural

abundance of 1.10%, what are the relative heights of the and

M+1 peaks in the mass spectrum of benzene, C6H6?

Question: What functional groups might the following molecules contain?

(a) A compound with a strong absorption at 1710cm-1

(b) A compound with a strong absorption at 1540cm-1

(c) A compound with strong absorptions at 1720cm-1 and 2500 to 3100 cm-1


Draw the structure of an alkene that yields only acetone, (CH3)2C=O, on ozonolysis followed by treatment with Zn.
See all solutions

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