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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

Draw and name the following

a) The eight carboxylic acids with the formula C6H12O2

b) Three nitriles with the formula C5H7N

Grignard reagents undergo a general and very useful reaction with

ketones. Methylmagnesium bromide, for example, reacts with cyclohexanoneto yield a product with the formula C7H14O . What is the structure of this product if it has an IR absorption at 3400 cm-1 ?

One consequence of the base-catalyzed isomerization of unsaturated ketones described in Problem 22-55 is that 2-substituted 2-cyclopentenones can be interconverted with 5-substituted 2-cyclopentenones. Propose a mechanism for this isomerization.

The following two hydrocarbons have been isolated from various plants in the sunflower family. Name them according to IUPAC rules.

The Favorskii reactioninvolves the treatment of an -bromo ketone with a base to yield a ring-contracted product. For example, the reaction of 2-bromocyclohexanone with aqueous NaOH yields cyclopentanecarboxylic acid. Propose a mechanism.
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