(a)
Interpretation:
The complete, detailed mechanism and the products are to be drawn for the given reaction.
Concept introduction:
Answer to Problem 21.39P
The complete mechanism is
The product of the reaction is
Explanation of Solution
The given reaction is
Alcohol is a weak nucleophile and adds to one of the carbonyl carbons of acetic anhydride to produce a protonated ether linkage. The carbonyl oxygen becomes negatively charged as a result of the
In the next step, the positively charged oxygen is deprotonated by another molecule of the alcohol.
The final step is nucleophilic elimination of acetate anion as a result of the lone pair of the negatively charged oxygen moving to reform the carbonyl group.
Thus, the complete mechanism of the reaction can be drawn as
The product of the reaction is
The product and mechanism of the given reaction are determined on the basis of nucleophilic addition-elimination mechanism.
(b)
Interpretation:
The complete, detailed mechanism and the products are to be drawn for the given reaction.
Concept introduction:
Carboxylic acid derivatives undergo acyl group substitution reactions when treated with appropriate nucleophiles. The reaction occurs via nucleophilic addition-elimination involving a tetrahedral intermediate. It may also involve proton transfer step(s), particularly when the nucleophile being added in the first step is not a strong nucleophile. The reaction occurs if the possible product is more stable than the reactant. If the two are of comparable stability, the reaction will occur reversibly. The order of increasing stability of acid derivatives is
Answer to Problem 21.39P
The complete mechanism is
The product of the reaction is
Explanation of Solution
The given reaction is
The
In the first step, it acts as a nucleophile and adds to the carbonyl carbon of the acid chloride to produce a protonated amine linkage. The
The protonated amine is then deprotonated by a second molecule of the amine.
Finally, one lone pair on the negatively charged oxygen will move back to reform the carbonyl group, eliminating the chloride and forming the product.
Thus, the complete mechanism can be drawn as
And the product of the reaction will be
The product and mechanism of the given reaction are determined on the basis of nucleophilic addition-elimination mechanism.
(c)
Interpretation:
The complete, detailed mechanism and the products are to be drawn for the given reaction.
Concept introduction:
Carboxylic acid derivatives undergo acyl group substitution reactions when treated with appropriate nucleophiles. The reaction occurs via nucleophilic addition-elimination involving a tetrahedral intermediate. It may also involve proton transfer step(s), particularly when the nucleophile being added in the first step is not a strong nucleophile. The reaction occurs if the possible product is more stable than the reactant. If the two are of comparable stability, the reaction will occur reversibly. The order of increasing stability of acid derivatives is
Answer to Problem 21.39P
The complete mechanism of the reaction is
The product of the reaction is
Explanation of Solution
The given reaction is
The amine will act as a nucleophile and add to the carbonyl carbon of the acid chloride in the first step to form a protonated amine linkage. The
The protonated amine is deprotonated in the second step by the added base, pyridine.
Finally, one lone pair on the negatively charged oxygen moves back to reform the carbonyl group, eliminating the leaving group chloride and forming the final product.
Thus, the complete mechanism can be drawn as
And the product of the reaction will be
The product and mechanism of the given reaction are determined on the basis of nucleophilic addition-elimination mechanism.
(d)
Interpretation:
The complete, detailed mechanism and the products are to be drawn for the given reaction.
Concept introduction:
Carboxylic acid derivatives undergo acyl group substitution reactions when treated with appropriate nucleophiles. The reaction occurs via nucleophilic addition-elimination involving a tetrahedral intermediate. It may also involve proton transfer step(s), particularly when the nucleophile being added in the first step is not a strong nucleophile. The reaction occurs if the possible product is more stable than the reactant. If the two are of comparable stability, the reaction will occur reversibly. The order of increasing stability of acid derivatives is
Answer to Problem 21.39P
The complete mechanism of the reaction is
The product of the reaction is
Explanation of Solution
The given reaction is
The alcohol is a weak nucleophile. It will add to one of the carbonyl carbons in the anhydride to produce a protonated intermediate.
In the seconds step, this intermediate will be deprotonated by a second molecule of the alcohol.
Finally, one lone pair from the negatively charged oxygen will move back to reform the carbonyl, eliminating the leaving group benzoate in the process and forming the product.
Thus, the complete mechanism can be drawn as
And the product of the reaction will be
The product and mechanism of the given reaction are determined on the basis of nucleophilic addition-elimination mechanism.
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Chapter 21 Solutions
EBK GET READY FOR ORGANIC CHEMISTRY
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- In the drawing area below, draw the major products of this organic reaction: If there are no major products, because nothing much will happen to the reactant under these reaction conditions, check the box under the drawing area instead. 1. NaH 2. CH3Br ? Click and drag to start drawing a structure. No reaction. : ☐ Narrow_forward+ Predict the major product of the following reaction. : ☐ + ☑ ค OH H₂SO4 Click and drag to start drawing a structure.arrow_forwardConsider this organic reaction: ... OH CI Draw the major products of the reaction in the drawing area below. If there won't be any major products, because this reaction won't happen at a significant rate, check the box under the drawing area instead. ☐ No Reaction. Click and drag to start drawing a structure. : аarrow_forward
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