What is the role of ammonium chloride in the workup of a Grignard reaction?
$begingroup$
In the following Grignard reaction, why is aqueous ammonium chloride used to get to the products? I don't see how it participated in or modified the reaction from what is normally expected.
organic-chemistry experimental-chemistry grignard-reagent
edited 2 days ago
A.K.
8,39341961
asked 2 days ago
Jhagrut LalwaniJhagrut Lalwani
466
New contributor
Jhagrut Lalwani is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
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add a comment |
$begingroup$
In the following Grignard reaction, why is aqueous ammonium chloride used to get to the products? I don't see how it participated in or modified the reaction from what is normally expected.
organic-chemistry experimental-chemistry grignard-reagent
edited 2 days ago
A.K.
8,39341961
asked 2 days ago
Jhagrut LalwaniJhagrut Lalwani
466
New contributor
Jhagrut Lalwani is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
$endgroup$
$begingroup$
This question has been edited to be more obviously on-topic.
$endgroup$
– A.K.
2 days ago
$begingroup$
In scientific writing, brevity is highly valued. I do not see the point of padding a post when the question is perfectly clear and answerable. It is a waste of time for the editor as well as for future readers. To make myself abundantly clear, I am not criticising the edit, but rather the situation which necessitates this edit.
$endgroup$
– orthocresol♦
2 days ago
add a comment |
$begingroup$
In the following Grignard reaction, why is aqueous ammonium chloride used to get to the products? I don't see how it participated in or modified the reaction from what is normally expected.
organic-chemistry experimental-chemistry grignard-reagent
edited 2 days ago
A.K.
8,39341961
asked 2 days ago
Jhagrut LalwaniJhagrut Lalwani
466
New contributor
Jhagrut Lalwani is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
$endgroup$
In the following Grignard reaction, why is aqueous ammonium chloride used to get to the products? I don't see how it participated in or modified the reaction from what is normally expected.
organic-chemistry experimental-chemistry grignard-reagent
organic-chemistry experimental-chemistry grignard-reagent
edited 2 days ago
A.K.
8,39341961
asked 2 days ago
Jhagrut LalwaniJhagrut Lalwani
466
New contributor
Jhagrut Lalwani is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
edited 2 days ago
A.K.
8,39341961
asked 2 days ago
Jhagrut LalwaniJhagrut Lalwani
466
New contributor
Jhagrut Lalwani is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
edited 2 days ago
A.K.
8,39341961
edited 2 days ago
A.K.
8,39341961
edited 2 days ago
A.K.
8,39341961
8,39341961
asked 2 days ago
Jhagrut LalwaniJhagrut Lalwani
466
New contributor
Jhagrut Lalwani is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
asked 2 days ago
Jhagrut LalwaniJhagrut Lalwani
466
asked 2 days ago
Jhagrut LalwaniJhagrut Lalwani
466
466
New contributor
Jhagrut Lalwani is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
New contributor
Jhagrut Lalwani is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
Jhagrut Lalwani is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
Check out our Code of Conduct.
$begingroup$
This question has been edited to be more obviously on-topic.
$endgroup$
– A.K.
2 days ago
$begingroup$
In scientific writing, brevity is highly valued. I do not see the point of padding a post when the question is perfectly clear and answerable. It is a waste of time for the editor as well as for future readers. To make myself abundantly clear, I am not criticising the edit, but rather the situation which necessitates this edit.
$endgroup$
– orthocresol♦
2 days ago
add a comment |
$begingroup$
This question has been edited to be more obviously on-topic.
$endgroup$
– A.K.
2 days ago
$begingroup$
In scientific writing, brevity is highly valued. I do not see the point of padding a post when the question is perfectly clear and answerable. It is a waste of time for the editor as well as for future readers. To make myself abundantly clear, I am not criticising the edit, but rather the situation which necessitates this edit.
$endgroup$
– orthocresol♦
2 days ago
$begingroup$
This question has been edited to be more obviously on-topic.
$endgroup$
– A.K.
2 days ago
$begingroup$
This question has been edited to be more obviously on-topic.
$endgroup$
– A.K.
2 days ago
$begingroup$
In scientific writing, brevity is highly valued. I do not see the point of padding a post when the question is perfectly clear and answerable. It is a waste of time for the editor as well as for future readers. To make myself abundantly clear, I am not criticising the edit, but rather the situation which necessitates this edit.
$endgroup$
– orthocresol♦
2 days ago
$begingroup$
In scientific writing, brevity is highly valued. I do not see the point of padding a post when the question is perfectly clear and answerable. It is a waste of time for the editor as well as for future readers. To make myself abundantly clear, I am not criticising the edit, but rather the situation which necessitates this edit.
$endgroup$
– orthocresol♦
2 days ago
add a comment |
1 Answer
1
active
oldest
votes
$begingroup$
Ammonium chloride ($ce{NH4Cl}$) is the work-up reagent that quenches the magnesium alkoxide product of the Grignard addition. It is the reagent of choice as it is a proton source without being acidic; acidic conditions could result in protonation of the tertiary alcohol product and elimination to the alkene. It also ensures that all inorganic salts of Mg will extract into the aqueous phase.
edited 2 days ago
orthocresol♦
38.7k7113235
answered 2 days ago
WaylanderWaylander
6,20711223
$endgroup$
2
$begingroup$
Oh I actually never knew that! In that case, other weak acids can also be used right? For example, what about weak organic acids like ethanoic acid?
$endgroup$
– Tan Yong Boon
2 days ago
2
$begingroup$
Yes, coud use that or something like sodium dihydrogen phosphate.
$endgroup$
– Waylander
2 days ago
add a comment |
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1 Answer
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active
oldest
votes
1 Answer
1
active
oldest
votes
active
oldest
votes
active
oldest
votes
$begingroup$
Ammonium chloride ($ce{NH4Cl}$) is the work-up reagent that quenches the magnesium alkoxide product of the Grignard addition. It is the reagent of choice as it is a proton source without being acidic; acidic conditions could result in protonation of the tertiary alcohol product and elimination to the alkene. It also ensures that all inorganic salts of Mg will extract into the aqueous phase.
edited 2 days ago
orthocresol♦
38.7k7113235
answered 2 days ago
WaylanderWaylander
6,20711223
$endgroup$
2
$begingroup$
Oh I actually never knew that! In that case, other weak acids can also be used right? For example, what about weak organic acids like ethanoic acid?
$endgroup$
– Tan Yong Boon
2 days ago
2
$begingroup$
Yes, coud use that or something like sodium dihydrogen phosphate.
$endgroup$
– Waylander
2 days ago
add a comment |
$begingroup$
Ammonium chloride ($ce{NH4Cl}$) is the work-up reagent that quenches the magnesium alkoxide product of the Grignard addition. It is the reagent of choice as it is a proton source without being acidic; acidic conditions could result in protonation of the tertiary alcohol product and elimination to the alkene. It also ensures that all inorganic salts of Mg will extract into the aqueous phase.
edited 2 days ago
orthocresol♦
38.7k7113235
answered 2 days ago
WaylanderWaylander
6,20711223
$endgroup$
2
$begingroup$
Oh I actually never knew that! In that case, other weak acids can also be used right? For example, what about weak organic acids like ethanoic acid?
$endgroup$
– Tan Yong Boon
2 days ago
2
$begingroup$
Yes, coud use that or something like sodium dihydrogen phosphate.
$endgroup$
– Waylander
2 days ago
add a comment |
$begingroup$
Ammonium chloride ($ce{NH4Cl}$) is the work-up reagent that quenches the magnesium alkoxide product of the Grignard addition. It is the reagent of choice as it is a proton source without being acidic; acidic conditions could result in protonation of the tertiary alcohol product and elimination to the alkene. It also ensures that all inorganic salts of Mg will extract into the aqueous phase.
edited 2 days ago
orthocresol♦
38.7k7113235
answered 2 days ago
WaylanderWaylander
6,20711223
$endgroup$
Ammonium chloride ($ce{NH4Cl}$) is the work-up reagent that quenches the magnesium alkoxide product of the Grignard addition. It is the reagent of choice as it is a proton source without being acidic; acidic conditions could result in protonation of the tertiary alcohol product and elimination to the alkene. It also ensures that all inorganic salts of Mg will extract into the aqueous phase.
edited 2 days ago
orthocresol♦
38.7k7113235
answered 2 days ago
WaylanderWaylander
6,20711223
edited 2 days ago
orthocresol♦
38.7k7113235
edited 2 days ago
orthocresol♦
38.7k7113235
edited 2 days ago
orthocresol♦
38.7k7113235
38.7k7113235
answered 2 days ago
WaylanderWaylander
6,20711223
answered 2 days ago
WaylanderWaylander
6,20711223
answered 2 days ago
WaylanderWaylander
6,20711223
6,20711223
2
$begingroup$
Oh I actually never knew that! In that case, other weak acids can also be used right? For example, what about weak organic acids like ethanoic acid?
$endgroup$
– Tan Yong Boon
2 days ago
2
$begingroup$
Yes, coud use that or something like sodium dihydrogen phosphate.
$endgroup$
– Waylander
2 days ago
add a comment |
2
$begingroup$
Oh I actually never knew that! In that case, other weak acids can also be used right? For example, what about weak organic acids like ethanoic acid?
$endgroup$
– Tan Yong Boon
2 days ago
2
$begingroup$
Yes, coud use that or something like sodium dihydrogen phosphate.
$endgroup$
– Waylander
2 days ago
2
2
$begingroup$
Oh I actually never knew that! In that case, other weak acids can also be used right? For example, what about weak organic acids like ethanoic acid?
$endgroup$
– Tan Yong Boon
2 days ago
$begingroup$
Oh I actually never knew that! In that case, other weak acids can also be used right? For example, what about weak organic acids like ethanoic acid?
$endgroup$
– Tan Yong Boon
2 days ago
2
2
$begingroup$
Yes, coud use that or something like sodium dihydrogen phosphate.
$endgroup$
– Waylander
2 days ago
$begingroup$
Yes, coud use that or something like sodium dihydrogen phosphate.
$endgroup$
– Waylander
2 days ago
add a comment |
Jhagrut Lalwani is a new contributor. Be nice, and check out our Code of Conduct.
Jhagrut Lalwani is a new contributor. Be nice, and check out our Code of Conduct.
Jhagrut Lalwani is a new contributor. Be nice, and check out our Code of Conduct.
Jhagrut Lalwani is a new contributor. Be nice, and check out our Code of Conduct.
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$begingroup$
This question has been edited to be more obviously on-topic.
$endgroup$
– A.K.
2 days ago
$begingroup$
In scientific writing, brevity is highly valued. I do not see the point of padding a post when the question is perfectly clear and answerable. It is a waste of time for the editor as well as for future readers. To make myself abundantly clear, I am not criticising the edit, but rather the situation which necessitates this edit.
$endgroup$
– orthocresol♦
2 days ago