Acetals can serve as protecting groups for 1,2-diols,as well as for aldehydes and ketones. When the acetal is formed from acetone plus the diol, the acetal is called as acetonide. Show the acetonides formed from these diols with acetone under acid catalysis.

Short Answer

Expert verified

A reaction of acetone with both hydroxyl groups of a diol forms a cyclic acetal, which is more commonly known as the acetonide.

Step by step solution

01

The definition of acetonide

A reaction of acetone with both hydroxyl groups of a diol forms a cyclic acetal, which is more commonly known as the acetonide.

02

Acetals as protecting groups

Acetals can be easily prepared from corresponding aldehydes and ketones and also it can be converted back to its starting carbonyl compounds. Due to this reason, acetals are very much useful is acting as protecting groups to prevent aldehydes and ketones from reacting with strong bases and nucleophiles.

03

The formation of acetonides from diol and acetone.

1,2-diols on treatment with acetone under acid catalysis (H+,H2O)forms a cyclic ketal (acetonide). The mechanism for the formation of an acetal can be divided into two parts, namely acid-catalyzed addition of a carbonyl which is followed by SN1substitution. Acetals are the most commonly used protecting groups for aldehydes and ketones. The formation of acetonides from the given diols is shown below:

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Most popular questions from this chapter

For each compound,

  1. Classify the nitrogen containing functional groups.
  2. Provide acceptable name

(a)

(b)

(c)

(d)

(e)

(f)

(g)

(h)

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.

(a) isopentyl alcohol isopentyl acetate (banana oil)

(b) 3-ethylpentanoic acid3-ethylpentanenitrile

(c) isobutylamineN-isobutylformamide

(d) ethyl acetate3-methylpentan-3-ol

(e) cyclohexylamineN-cyclohexylacetamide

(f) bromocyclohexanedicyclohexylmethano

(g)

(h)

Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for driving the reaction to completion.

(a)methyl salicylate

(b) methyl formate (32°C)

(c) ethyl phenylacetate

Question: Draw the structures of the following compounds.

  1. propanoic acid
  2. phthalic acid
  3. calciumformate
  4. succinic acid
  5. dibromoacetic acid
  6. acetylsalicylate (aspirin)
  7. zincdecanoate (athlete's-foot powder)
  8. potassium benzoate (a food preservative)
  9. potassium fluoroacetate

The 2000 Nobel Prize in Chemistry was awarded for work on polyacetylenes. Acetylene can be polymerized using a Ziegler-Natta catalyst. The cis or trans stereochemistry of the products can be controlled by careful selection and preparation of the catalyst. The resulting polyacetylene is an electrical semiconductor with a metallic appearance. cis-Polyacetylene has a copper color, and trans-polyacetylene is silver.

(a) Draw the structures of cis- and trans-polyacetylene.

(b) Use your structures to show why these polymers conduct electricity.

(c) It is possible to prepare polyacetylene films whose electrical conductivity is anisotropic. That is, the conductivity is higher in some directions than in others. Explain how this unusual behavior is possible.

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