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(a)
Interpretation:
The product of the reaction between actic anhydride and the given reactant is to be predicted. A complete, detailed mechanism is to be drawn if the reaction occurs.
Concept introduction:
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Answer to Problem 20.36P
The product of the given reaction is
The complete mechanism of the reaction is
Explanation of Solution
The given reactant is NaOH followed by
Thus, the product of the reaction will be
The reaction will start with the nucleophilic addition of hydroxide ion from NaOH, producing a tetrahedral intermediate.
In the second step, one lone pair from negatively charged oxygen will move back to the carbon to reform the carbonyl group and eliminate an acetate ion. This step will produce one acetate ion and one acetic acid molecule, but under the strongly basic conditions, the acid will be irreversibly deprotonated to produce two carboxylate anions.
The addition of the acid (
Thus, the complete mechanism can be drawn as
The product of the reaction and its mechanism were determined based on the relative stability of the produc, and the nucleophilic addition-elimination mechanism.
(b)
Interpretation:
The product of the reaction between acetic anhydride and the given reactant is to be predicted. A complete, detailed mechanism is to be drawn if the reaction occurs.
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). 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
![Check Mark](/static/check-mark.png)
Answer to Problem 20.36P
The products of the given reaction are
The complete mechanism of the reaction is
Explanation of Solution
The given reactant is
One lone pair on negatively charged oxygen will move back toward the carbon to reform the carbnyl group and eliminate an acetate ion to form the final product.
Thus, the product of the reaction will be
And the complete mechanism can be drawn as
The product of the reaction and its mechanism were dsetermined based on the relative stability of the product and the nucleophilic addition-elimination mechanism.
(c)
Interpretation:
The product of the reaction between acetic anhydride and the given reactant is to be predicted. A complete, detailed mechanism is to be drawn if the reaction occurs.
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). 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
![Check Mark](/static/check-mark.png)
Answer to Problem 20.36P
The product of the given reaction is
The complete mechanism of the reaction is
Explanation of Solution
The given reactant is
Therefore, the product of the reaction will be
In the first step, the incoming nucleophile will add to the carbonyl carbon, producing a tetrahedral intermediate.
The lone pair on negativey charged ocygen will move back toward the carbon to reform the carbonyl group and eliminate acetate anion to form the final product, an ester.
Thus, the complete mechanism can be drawn as
The product of the reaction and its mechanism were dsetermined based on the relative stability of the product and the nucleophilic addition-elimination mechanism.
(d)
Interpretation:
The product of the reaction between aceetic anhydride and the given reactant is to be predicted. A complete, detailed mechanism is to be drawn if the reaction occurs.
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). 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
![Check Mark](/static/check-mark.png)
Answer to Problem 20.36P
The product of the given reaction is
The complete mechanism of the reaction is
Explanation of Solution
The given reactant is
Therefore, the product of the reaction will be
In the first step, the nucleophile will add to the carbonyl carbon to produce a tetrahedral intermediate.
In the second step, one lone pair of negatively charged oxygen will move back to the carbon to reform the carbonyl group and eliminate acetate anion to form the final product.
Thus, the complete mechanism can be drawn as
The product of the reaction and its mechanism were dsetermined based on the relative stability of the product and the nucleophilic addition-elimination mechanism.
(e)
Interpretation:
The product of the reaction between acetic anhydride and the given reactant is to be predicted. A complete, detailed mechanism is to be drawn if the reaction occurs.
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). 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
![Check Mark](/static/check-mark.png)
Answer to Problem 20.36P
There will be no reaction.
Explanation of Solution
The given reactant is NaBr, a source of the nucelophile
Therefore, the reaction will not occur.
Nucleophilic addition-elimination cannot occur since the possible product is of lower stability than the reactant.
(f)
Interpretation:
The product of the reaction between acetic anhydride and the given reactant is to be predicted. A complete, detailed mechanism is to be drawn if the reaction occurs.
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). 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
![Check Mark](/static/check-mark.png)
Answer to Problem 20.36P
The reaction will not occur.
Explanation of Solution
The given reactant is
Therefore, there will be no reaction.
Nucleophilic addition-elimination is not possible in this case as the nucleophile is weak and does not add to a carbonyl carbon.
(g)
Interpretation:
The product of the reaction between acetic anhydride and the given reactant is to be predicted. A complete, detailed mechanism is to be drawn if the reaction occurs.
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). 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
![Check Mark](/static/check-mark.png)
Answer to Problem 20.36P
The reaction will not occur.
Explanation of Solution
The given reactant is
Therefore, there will be no reaction.
Nucleophilic addition-elimination is not possible in this case as the given reactant is an electrophile.
(h)
Interpretation:
The product of the reaction between acetic anhydride and the given reactant is to be predicted. A complete, detailed mechanism is to be drawn if the reaction occurs.
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). 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
![Check Mark](/static/check-mark.png)
Answer to Problem 20.36P
The reaction will not occur.
Explanation of Solution
The given reactant is hexanal with an electrophilic carbon.
Therefore, there will be no reaction.
Nucleophilic addition-elimination is not possible in this case as the reactant is an electrophile.
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Chapter 20 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
- टे Predict the major products of this organic reaction. Be sure to use wedge and dash bonds when necessary, for example to distinguish between different major products. ☐ ☐ : ☐ + NaOH HO 2 Click and drag to start drawing a structure.arrow_forwardShown below are five NMR spectra for five different C6H10O2 compounds. For each spectrum, draw the structure of the compound, and assign the spectrum by labeling H's in your structure (or in a second drawing of the structure) with the chemical shifts of the corresponding signals (which can be estimated to nearest 0.1 ppm). IR information is also provided. As a reminder, a peak near 1700 cm-1 is consistent with the presence of a carbonyl (C=O), and a peak near 3300 cm-1 is consistent with the presence of an O–H. Extra information: For C6H10O2 , there must be either 2 double bonds, or 1 triple bond, or two rings to account for the unsaturation. There is no two rings for this problem. A strong band was observed in the IR at 1717 cm-1arrow_forwardPredict the major products of the organic reaction below. : ☐ + Х ك OH 1. NaH 2. CH₂Br Click and drag to start drawing a structure.arrow_forward
- NG NC 15Show all the steps you would use to synthesize the following products shown below using benzene and any organic reagent 4 carbons or less as your starting material in addition to any inorganic reagents that you have learned. NO 2 NC SO3H NO2 OHarrow_forwardDon't used hand raiting and don't used Ai solutionarrow_forwardShow work...don't give Ai generated solutionarrow_forward
- 1 Please provide an efficient synthesis of the product below from the starting material. Use the starting material as the ONLY source of carbon atoms. Show the synthesis of each compound that would be used in the overall synthesis of the product. [This synthesis uses alkyne and alcohol chemistry.]arrow_forward10- 4000 20 20 30- %Reflectance 60 50- 09 60- 40- Date: Thu Feb 06 17:30:02 2025 (GMT-05:0(UnknownP Scans: 8 Resolution: 2.000 70 70 88 80 3500 3000 2500 90 100 00 Wavenumbers (cm-1) 2000 1500 2983.10 2359.13 1602.52 1584.22 1451.19 1391.87 1367.07 1314.37 1174.34 1070.13 1027.33 1714.16 1269.47 1000 1106.08 1001.14 937.02 873.60 850.20 780.22 686.91 674.38 643.09 617.98 02/06/25 16:38:20arrow_forwardd. Draw arrow-pushing mechanism for an enzymatic retro-aldol reaction of the following hexose. Use B: and/or HA as needed. OH OH سية HO OH OHarrow_forward
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