20. Carboxylic Acid Derivatives:NAS
Nucleophilic Acyl Substitution
20. Carboxylic Acid Derivatives:NAS
Nucleophilic Acyl Substitution - Video Tutorials & Practice Problems
On a tight schedule?
Get a 10 bullets summary of the topicIt's time to learn about The 3 Rules for Nucleophilic Acyl Substitution. Are you ready?
1
concept
NAS - The Three Rules
Video duration:
9mPlay a video:
RULE 1: General Reactions
![Content](https://cdn.clutchprep.com/guide_visuals/inline_images/JfjQpD9ZhqahyztDufndTw.png)
RULE 2: More reactive acyl compounds can be easily converted into less reactive ones.
![Content](https://cdn.clutchprep.com/guide_visuals/inline_images/vDYA2E6xSCNDpSyU6oVfdQ.png)
RULE 3: Carboxylic Acid Conversions
![Content](https://cdn.clutchprep.com/guide_visuals/inline_images/Hkf3y5mV3b0flQQF2FyWaA.png)
2
Problem
ProblemDetermine the major product for the following reaction.
A
B
C
D
3
Problem
ProblemDetermine the major product for the following reaction.
A
B
C
D
4
Problem
ProblemDetermine the major product for the following reaction.
A
B
C
D
5
Problem
ProblemDetermine the major product for the following reaction.
A
B
C
D
Do you want more practice?
We have more practice problems on Nucleophilic Acyl Substitution
Your Organic Chemistry tutors
Additional resources for Nucleophilic Acyl Substitution
PRACTICE PROBLEMS AND ACTIVITIES (95)
- What compounds are formed from the reaction of benzoyl chloride with the following reagents? g. excess benzyl...
- What acyl chloride and amine are required to synthesize the following amides? a. N-ethylbutanamide b. N,N-di...
- Write the mechanism for each of the following reactions: b. the reaction of benzoyl chloride with excess meth...
- What compounds are formed from the reaction of benzoyl chloride with the following reagents? a. sodium acetat...
- Starting with methyl acetate, what neutral nucleophile would you use to synthesize each of the following compo...
- Identify the major and minor products of the following reaction: + —>
- a. When a carboxylic acid is dissolved in isotopically labeled water (H2O18) and an acid catalyst is added, th...
- An aqueous solution of a primary or secondary amine reacts with an acyl chloride to form an amide as the major...
- a. Identify the two products obtained from the following reaction: excess + —>
- What reagent should be used to carry out the following reaction? —>
- What are the products of the following reactions? a. CH3C=O(Cl) + KF —> b. + H2O HCl Δ—>
- Give the products expected from the following reactions. (a) acetyl chloride + ethylamine (b) < of reaction...
- Draw the product of each of the following reactions: b.
- What are the products of the following reactions? a.
- Propose mechanisms for the nucleophilic acyl substitutions to form N-methylacetamide as shown on the previous ...
- Propose mechanisms for the nucleophilic acyl substitutions to form ethyl benzoate as shown on the previous pag...
- Predict the products and propose mechanisms for the following reactions. (d)
- Predict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents. (a) etha...
- Show how you would use appropriate acyl chlorides and amines to synthesize the following amides. (c) cyclohex...
- Show how you would synthesize the following esters from appropriate acyl chlorides and alcohols. (a) ethyl p...
- Which of the following proposed reactions would take place quickly under mild conditions? (a) (b) (c) (d) ...
- (d) Propose a mechanism for the reaction of aniline with acetic anhydride to give acetanilide.
- (b) Propose a mechanism for the reaction of benzoic acid with acetyl chloride to give acetic benzoic anhydride...
- (a) Propose a mechanism for the reaction of benzyl alcohol with acetyl chloride to give benzyl acetate
- Show how you would accomplish the following synthetic conversions efficiently and in good yield. You may use a...
- Show how you would use an acid chloride as an intermediate to synthesize.(a) N-phenylbenzamide (PhCONHPh) from...
- Show how you would convert the following starting materials to the indicated nitriles:(a) phenylacetic acid --...
- Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.(a) <IMAGE>...
- Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.(b) <IMAGE>...
- Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.(c) <IMAGE>...
- (c) Propose a second mechanism for the reaction of benzoic acid with acetyl chloride to give acetic benzoic an...
- (e) Propose a mechanism for the reaction of aniline with ethyl acetate to give acetanilide. What is the leavin...
- Show how you would synthesize the following esters from appropriate acyl chlorides and alcohols. (e) tert-but...
- Show how you would use appropriate acyl chlorides and amines to synthesize the following amides.(a) N,N-dimeth...
- (a) Show how you would use acetic anhydride and an appropriate alcohol or amine to synthesize (i) benzyl aceta...
- Show how you would accomplish the following syntheses. Some of these conversions may require more than one ste...
- Predict the products of the following reactions.(a) <IMAGE>
- Predict the products of the following reactions.(b) <IMAGE>
- Predict the products of the following reactions.(k) <IMAGE>
- Predict the products of the following reactions.(l) <IMAGE>
- Show how you would accomplish the following syntheses in good yields.(g) <IMAGE>
- Propose a mechanism for the reaction of benzyl acetate with methylamine. Label the attacking nucleophile and t...
- Show how you would use anhydrides to synthesize the following compounds. In each case, explain why an anhydrid...
- Predict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents.(d) anisol...
- Predict the products of the following reactions.(e) <IMAGE>(f) <IMAGE>
- One mole of acetyl chloride is added to a liter of triethylamine, resulting in a vigorous exothermic reaction....
- Phosgene is the acid chloride of carbonic acid. Although phosgene was used as a war gas in World War I, it is ...
- Suggest the most appropriate reagent for each synthesis, and explain your choice.(a) <IMAGE>
- There are many methods for activating a carboxylic acid in preparation for coupling with an amine. The followi...
- (c) Diethyl carbonate is a liquid reagent that is easy to handle. Also show how you might use diethyl carbonat...
- Suggest the most appropriate reagent for each synthesis, and explain your choice.(d) <IMAGE>
- Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solve...
- How would you make the following compounds from N-benzylbenzamide? c. benzyl alcohol
- The reaction of a nitrile with an alcohol in the presence of a strong acid forms an N-substituted amide. This ...
- The reaction of a nitrile with an alcohol in the presence of a strong acid forms an N-substituted amide. This ...
- The reaction of a nitrile with an alcohol in the presence of a strong acid forms an N-substituted amide. This ...
- a. Which of the following reactions does not give the carbonyl product shown? b. Which of the reactions that ...
- a. Which of the following reactions does not give the carbonyl product shown? b. Which of the reactions that ...
- b. Explain why the rate of aminolysis of an ester cannot be increased by H+.
- b. Explain why the rate of aminolysis of an ester cannot be increased by HO−, or RO-.
- a. Rank the following esters from most reactive to least reactive in the first slow step of a nucleophilic acy...
- Rank the same esters from most reactive to least reactive in the second slow step of a nucleophilic acyl subst...
- In each part, rank the compounds in order of increasing rate of nucleophilic attack at C=O by a strong nucleop...
- Show how you would convert 2-methylcyclopentanol to the following products. Any of these products may be used...
- Predict the product of the multistep synthesis reaction shown.
- Predict the product of the following reaction sequences. (a)
- How can the following compounds be prepared from the given starting materials? a.
- Show how you would synthesize each compound, starting with an ester containing no more than eight carbon atoms...
- Show how to synthesize the following amines from the indicated starting materials by acylation–reduction. (a)...
- Which compound forms an anhydride more rapidly?
- b. What is the product of the reaction of acetamide with HO−? The pKa of NH3 is 36; the pKa of H2O is 15.7.
- What is the product of an acyl substitution reaction—a new carboxylic acid derivative, a mixture of two carbo...
- What is the product of an acyl substitution reaction—a new carboxylic acid derivative, a mixture of two carbo...
- Using the pKa values listed in [TABLE 15.1] , predict the products of the following reactions: c. + NaCl —&g...
- Using the pKa values listed in [TABLE 15.1] , predict the products of the following reactions: d. + NaOH —&g...
- Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following comp...
- Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following comp...
- Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following comp...
- Starting with acetyl chloride, what neutral nucleophile would you use to synthesize each of the following comp...
- Write a mechanism for each of the following reactions: b. the aminolysis of phenyl formate, using methylamine...
- Write the mechanism for the acid-catalyzed reaction of an amide with an alcohol to form an ester.
- a. Propose a mechanism for the reaction of acetic anhydride with water.
- We saw that acid anhydrides react with alcohols, water, and amines. In which of these reactions can the tetrah...
- a. Propose a mechanism for the formation of succinic anhydride from succinic acid in the presence of acetic an...
- b. How does acetic anhydride make it easier to form the anhydride?
- What compounds are formed from the reaction of benzoyl chloride with the following reagents? e. aqueous NaOH
- What compounds are formed from the reaction of benzoyl chloride with the following reagents? f. cyclohexanol
- What compounds are formed from the reaction of benzoyl chloride with the following reagents? i. isopropyl alc...
- What compounds are formed from the reaction of benzoyl chloride with the following reagents? k. potassium for...
- What compounds are obtained from the following hydrolysis reactions? d. CH3CH2C=O(O)C=O(CH3) + H2O —>
- What products would you expect to obtain from the following reactions? a. malonic acid+2 acetyl chloride
- What products would you expect to obtain from the following reactions? b. methyl carbamate + methylamine
- Show how the following compounds can be prepared from the given starting materials. You can use any necessary ...
- Propose a mechanism for each of the following reactions: b.
- Diazomethane can be used to convert a carboxylic acid to a methyl ester. Propose a mechanism for this reaction...