Why do esters, carboxylic acids and amides undergo acyl substitution but aldehydes and ketones cannot?
Why do esters, carboxylic acids and amides undergo acyl substitution but aldehydes and ketones cannot?
Homework Answers
ANSWER- Ketones and aldehyde do not undergo acyl substitution because there is no such leaving group present. For acyl substitution reactions, a nucleophile – such as an alcohol, amine, or enolate – displaces the leaving group of an acyl derivative – such as an acid halide, anhydride, or ester. The resulting product is a carbonyl-containing compound in which the nucleophile has taken the place of the leaving group present in the original acyl derivative.
Esters,carboxylic acids and amide undergo this type of reactions because they posses leaving group.
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Why do esters, carboxylic acids and amides undergo acyl substitution but aldehydes and ketones cannot?
The reactivity sequence of carboxylic acid derivatives (acyl halides, anhydrides, acids, esters, amides) changes with t...
The reactivity sequence of carboxylic acid derivatives (acyl halides, anhydrides, acids, esters, amides) changes with the substituent. Acyl chlorides are most reactive, amides are least reactive. 1) Explain in detail why the reactivity changes in that sequence, 2) Where do carboxylates fit in that sequence and why? How does that impact on the way carboxylic acid reactions need to run? 3) Where do thioesters, RC(-O)SMe and acyl phosphates, RC(-O)OPO2OR fit in that sequence. Explain your decision
The reactivity sequence of...
9) 9) Why do aldehydes undergo nucleophilic addition reactions, whereas esters undergo nucleophilic acyl substitution reactions?...
9) 9) Why do aldehydes undergo nucleophilic addition reactions, whereas esters undergo nucleophilic acyl substitution reactions? A) The carbonyl carbon of an ester is more electrophilic than that of an aldehyde. B) Once the nucleophile adds to an aldehyde, neither H- nor R-can be eliminated because they are strongly basic. C) Aldehydes are more sterically hindered than esters. D) The ester carbonyl carbon is sp3 hybridized while the aldehyde carbonyl carbon is sp2 hybridized. E) Once the nucleophile adds to...
Answer the following questions with only one answer a. Carboxylic acid derivatives cannot be hydrolyzed to...
Answer the following questions with only one answer a. Carboxylic acid derivatives cannot be hydrolyzed to produce carboxylic acids b. Lithium aluminum (tri-butoxy)hydride will convert acid chlorides to ketones c. Amides have more resonance stability than esters d. Nitriles are less basic than primary amines e. Grignard reagents contain polar covalent carbon-magnesium bonds f. Anhydrides are more reactive than esters in nucleophilic acyl substitution reactions g. Acid chlorides undergo nucleophilic acyl substitution reactions h. Nitriles have an sp hybridized Nitrogen...
Why do aldehydes undergo nucleophilic addition reactions while acyl chlorides undergo nucleophilic acyl substitution reactions? Once...
Why do aldehydes undergo nucleophilic addition reactions while acyl chlorides undergo nucleophilic acyl substitution reactions? Once the nucleophile adds to the aldehyde, the tetrahedral intermediate is too sterically hindered to eliminate one of the attached groups. Because an Sw2 substitution can best take place on the sphybridized carborwyl carbon of the acyl halide. Once the nucleophile adds to the aldehyde, neither H" nor Rºcan function as a leaving group. so a substitution cannot take place. The carbonyl carbon of the...
1. Aldehydes, ketones, acids, esters and amides. Write the name of the tu group under its...
1. Aldehydes, ketones, acids, esters and amides. Write the name of the tu group under its structure. O OCH CH3 HO O HyC-CH2-CH2-6 CH2 -CH H₂C HUN 2. Acetals and hemiacetals. Write the name of the functional group under its structure. OCH3 OCH CH3 Hąc но осна OH ГОСНЫ 3. Draw the structure when each of these undergoes hydrolysis. но осн. Н,0 H3CO OCH H* H20 H осн,сн ochyCH, *** H2O 4. What is the product of this reaction? Circle...
(7 points) Explain why esters are more reactive towards nucleophilic acyl substitution compared to amides. Your...
(7 points) Explain why esters are more reactive towards nucleophilic acyl substitution compared to amides. Your answer should be clear and concise. Writing more than necessary only increases the odds of writing an incorrect statement, which could result in points off. nucleophilic acyl substitution Nu R X R Nu - - - - - - - - - - O RO R NO Ester Amide
_15. The class least reactive towards acyl substitution is a. carboxylates b. esters c. acid anhydrides...
_15. The class least reactive towards acyl substitution is a. carboxylates b. esters c. acid anhydrides d. carboxylic acids e. acid halides f. amides _ 16. Acetals protect aldehyde carbonyl groups from all of the following except: a. acidic conditions b. nucleophiles c. organometallics H h O d. basic conditions are. hydride reduction
Name Structure Examples Alcohols Ethers Aldehydes Ketones Carboxylic Acids Ester
Name Structure Examples Alcohols Ethers Aldehydes Ketones Carboxylic Acids Ester
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The reactivity sequence of carboxylic acid derivatives (acyl halides, anhydrides, acids, esters, amides) changes with the substituent. Acyl chlorides are most reactive, amides are least reactive. 1) Explain in detail why the reactivity changes in that sequence, 2) Where do carboxylates fit in that sequence and why? How does that impact on the way carboxylic acid reactions need to run? 3) Where do thioesters, RC(-O)SMe and acyl phosphates, RC(-O)OPO2OR fit in that sequence. Explain your decision
The reactivity sequence of...
9) 9) Why do aldehydes undergo nucleophilic addition reactions, whereas esters undergo nucleophilic acyl substitution reactions? A) The carbonyl carbon of an ester is more electrophilic than that of an aldehyde. B) Once the nucleophile adds to an aldehyde, neither H- nor R-can be eliminated because they are strongly basic. C) Aldehydes are more sterically hindered than esters. D) The ester carbonyl carbon is sp3 hybridized while the aldehyde carbonyl carbon is sp2 hybridized. E) Once the nucleophile adds to...
Answer the following questions with only one answer a. Carboxylic acid derivatives cannot be hydrolyzed to produce carboxylic acids b. Lithium aluminum (tri-butoxy)hydride will convert acid chlorides to ketones c. Amides have more resonance stability than esters d. Nitriles are less basic than primary amines e. Grignard reagents contain polar covalent carbon-magnesium bonds f. Anhydrides are more reactive than esters in nucleophilic acyl substitution reactions g. Acid chlorides undergo nucleophilic acyl substitution reactions h. Nitriles have an sp hybridized Nitrogen...
Why do aldehydes undergo nucleophilic addition reactions while acyl chlorides undergo nucleophilic acyl substitution reactions? Once the nucleophile adds to the aldehyde, the tetrahedral intermediate is too sterically hindered to eliminate one of the attached groups. Because an Sw2 substitution can best take place on the sphybridized carborwyl carbon of the acyl halide. Once the nucleophile adds to the aldehyde, neither H" nor Rºcan function as a leaving group. so a substitution cannot take place. The carbonyl carbon of the...
1. Aldehydes, ketones, acids, esters and amides. Write the name of the tu group under its structure. O OCH CH3 HO O HyC-CH2-CH2-6 CH2 -CH H₂C HUN 2. Acetals and hemiacetals. Write the name of the functional group under its structure. OCH3 OCH CH3 Hąc но осна OH ГОСНЫ 3. Draw the structure when each of these undergoes hydrolysis. но осн. Н,0 H3CO OCH H* H20 H осн,сн ochyCH, *** H2O 4. What is the product of this reaction? Circle...
(7 points) Explain why esters are more reactive towards nucleophilic acyl substitution compared to amides. Your answer should be clear and concise. Writing more than necessary only increases the odds of writing an incorrect statement, which could result in points off. nucleophilic acyl substitution Nu R X R Nu - - - - - - - - - - O RO R NO Ester Amide
_15. The class least reactive towards acyl substitution is a. carboxylates b. esters c. acid anhydrides d. carboxylic acids e. acid halides f. amides _ 16. Acetals protect aldehyde carbonyl groups from all of the following except: a. acidic conditions b. nucleophiles c. organometallics H h O d. basic conditions are. hydride reduction
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