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Chapter 22: Q16. (page 892)

Question: Draw the products of each reaction.

a.

b.

c.

d.

Short Answer

Expert verified

Answer

a.

b.

c.

d.

Step by step solution

01

Step-by-Step Solution  Step 1: Fischer-esterification

Carboxylic acids react with alcohol in the presence of acids to form the corresponding ester. This reaction is known as the Fischer-esterification reaction.

It鈥檚 a two-step reaction involving the addition of nucleophiles and the elimination of leaving groups.

02

Reaction of carboxylic acid

a. Carboxylic acid reacts with an alcohol in an acidic medium to form an ester.

Reaction with alcohol

b. Carboxylic acid reacts with an alcohol in an acidic medium to form an ester.

Reaction with alcohol

c. NaOCH3 acts as a base and abstracts the acidic proton to form the corresponding sodium salt.

Reaction with base

d. Acid and alcohol are present in the same molecule. Therefore, intramolecular cyclization will occur in the acidic medium to form cyclic ester (lactone).


Formation of cyclic ester

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Most popular questions from this chapter

Question: Draw the three possible resonance structures for an acid bromide, . Then, using the pKa values in Appendix A, decide if RCOBr is more or less stabilized by resonance than a carboxylic acid (RCOOH).

Question: Explain why CH3CONH2 is a stronger acid and a weaker base than CH3CH2NH2 .

Question: (a) Give an acceptable name for each compound. (b) Draw the organic products formed when A or B is treated with each reagent: [1]H3O+;[2]-OH,H2O;[3]CH3CH2CH2MgBr(excess), then H2O; [4] LiAlH4,ThenH2O, then .

Question: Draw a stepwise mechanism for the formation of A from an alcohol and acid chloride. A was converted in one step to Blattella quinone, the sex pheromone of the female German cockroach Blattella germanica.

Draw the products formed when A or B is treated with each reagent. In some cases, no reaction occurs.

  1. NaBH4, CH3OH
  2. [1] LiAlH4 ; [2] H2O
  3. [1] CH3MgBr ; [2] H2O
  4. [1]C6H5Li ; [2] H2O
  5. Na2Cr2O7, H2SO4,H2O
See all solutions

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