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Chapter 20: Q6P (page 1038)

Show how you would synthesize each compound from starting materials containing no more than six carbon atoms.

Short Answer

Expert verified

Carbonyl compounds (aldehydes and ketons) reacts with RMgX to form alcholos as the major product. Aldehyde gives secondary alchols whereas ketone gives tertiary alcohols.

Step by step solution

01

Reaction of Carbonyl Compound

Carbonyl compounds (aldehydes and ketons) reacts with RMgX to form alcholos as the major product. Aldehyde gives secondary alchols whereas ketone gives tertiary alcohols.

02

Synthetic methodology

a. 1-bromo cyclohexane is first treated with magnesium in the presence of ether to form grignard reagent (cyclohexylmagnesium bromide). The so formed grignard reagent undergoes hydrolysis to form an alcohol. Again, the alcohol is oxidised by PCC to form the target compound. The corresponding reactions are shown below.


b. Benzene can be converted to propiophenone by Friedel Crafts acylation reaction. In this reaction, benzene combine with propanoyl chloride in the presence of Lewis acid AlCl3 to form an aromatic ketone (propiophenone). The corresponding reaction is shown.


c. 1-bromocyclopentane is first treated with magnesium in the presence of ether to form grignard reagent (cyclopentylmagnesium bromide). The so formed grignard reagent undergoes treatment with epoxide and subsequent hydrolysis to form an alcohol. Again, the alcohol is oxidised by PCC to form the target compound. The corresponding reactions are shown below.


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Most popular questions from this chapter

Question: A carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons.

  1. Draw the resonance forms of a carboxylic acid that is protonated on the hydroxy oxygen atom.
  2. Compare the resonance forms with those given previously for an acid protonated on the carbonyl oxygen atom.
  3. Explain why the carbonyl oxygen atom of a carboxylic acid is more basic than the hydroxy oxygen.

Question: Rank the following isomers in order of increasing boiling point, and explain the reasons for your order of ranking.

Predict the products obtained from the reaction of oleic acid with the following reagents.

  1. NaOH in water
  2. H2and a nickel catalyst
  3. Br2 in CCl4
  4. Ozone, then dimethyl sulfide
  5. Warm KmnO4in water
  6. CH2I2/ Zn(Cu)

Show how you would synthesize 2-phenylhex-3-yn-2-ol, starting with acetophenone (PhCOCH3 ) and any other reagents you need. (“2-ol” means there is an OH group on C2.)

The following reaction takes place under second-order conditions (strong nucleophile), yet the structure of the product shows rearrangement. Also, the rate of this reaction is several thousand times faster than the rate of substitution of hydroxide ion on 2-chlorobutane under similar conditions. Propose a mechanism to explain the enhanced rate and rearrangement observed in this unusual reaction. (“Et” is the abbreviation for ethyl.
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