What is the role of ammonium chloride in the workup of a Grignard reaction?
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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 Jan 18 at 23:48
A.K.
8,41841961
asked Jan 18 at 10:33
Jhagrut LalwaniJhagrut Lalwani
446
New contributor
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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 Jan 18 at 23:48
A.K.
8,41841961
asked Jan 18 at 10:33
Jhagrut LalwaniJhagrut Lalwani
446
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.
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$begingroup$
This question has been edited to be more obviously on-topic.
$endgroup$
– A.K.
Jan 18 at 23:50
$begingroup$
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♦
Jan 18 at 23:55
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 Jan 18 at 23:48
A.K.
8,41841961
asked Jan 18 at 10:33
Jhagrut LalwaniJhagrut Lalwani
446
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 Jan 18 at 23:48
A.K.
8,41841961
asked Jan 18 at 10:33
Jhagrut LalwaniJhagrut Lalwani
446
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 Jan 18 at 23:48
A.K.
8,41841961
asked Jan 18 at 10:33
Jhagrut LalwaniJhagrut Lalwani
446
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 Jan 18 at 23:48
A.K.
8,41841961
edited Jan 18 at 23:48
A.K.
8,41841961
edited Jan 18 at 23:48
A.K.
8,41841961
8,41841961
asked Jan 18 at 10:33
Jhagrut LalwaniJhagrut Lalwani
446
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 Jan 18 at 10:33
Jhagrut LalwaniJhagrut Lalwani
446
asked Jan 18 at 10:33
Jhagrut LalwaniJhagrut Lalwani
446
446
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.
Jan 18 at 23:50
$begingroup$
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♦
Jan 18 at 23:55
add a comment |
$begingroup$
This question has been edited to be more obviously on-topic.
$endgroup$
– A.K.
Jan 18 at 23:50
$begingroup$
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♦
Jan 18 at 23:55
$begingroup$
This question has been edited to be more obviously on-topic.
$endgroup$
– A.K.
Jan 18 at 23:50
$begingroup$
This question has been edited to be more obviously on-topic.
$endgroup$
– A.K.
Jan 18 at 23:50
$begingroup$
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♦
Jan 18 at 23:55
$begingroup$
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♦
Jan 18 at 23:55
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 Jan 18 at 10:59
orthocresol♦
38.7k7113235
answered Jan 18 at 10:39
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
Jan 18 at 12:09
2
$begingroup$
Yes, coud use that or something like sodium dihydrogen phosphate.
$endgroup$
– Waylander
Jan 18 at 12:36
add a comment |
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1 Answer
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1 Answer
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oldest
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active
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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 Jan 18 at 10:59
orthocresol♦
38.7k7113235
answered Jan 18 at 10:39
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
Jan 18 at 12:09
2
$begingroup$
Yes, coud use that or something like sodium dihydrogen phosphate.
$endgroup$
– Waylander
Jan 18 at 12:36
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 Jan 18 at 10:59
orthocresol♦
38.7k7113235
answered Jan 18 at 10:39
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
Jan 18 at 12:09
2
$begingroup$
Yes, coud use that or something like sodium dihydrogen phosphate.
$endgroup$
– Waylander
Jan 18 at 12:36
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 Jan 18 at 10:59
orthocresol♦
38.7k7113235
answered Jan 18 at 10:39
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 Jan 18 at 10:59
orthocresol♦
38.7k7113235
answered Jan 18 at 10:39
WaylanderWaylander
6,20711223
edited Jan 18 at 10:59
orthocresol♦
38.7k7113235
edited Jan 18 at 10:59
orthocresol♦
38.7k7113235
edited Jan 18 at 10:59
orthocresol♦
38.7k7113235
38.7k7113235
answered Jan 18 at 10:39
WaylanderWaylander
6,20711223
answered Jan 18 at 10:39
WaylanderWaylander
6,20711223
answered Jan 18 at 10:39
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
Jan 18 at 12:09
2
$begingroup$
Yes, coud use that or something like sodium dihydrogen phosphate.
$endgroup$
– Waylander
Jan 18 at 12:36
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
Jan 18 at 12:09
2
$begingroup$
Yes, coud use that or something like sodium dihydrogen phosphate.
$endgroup$
– Waylander
Jan 18 at 12:36
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
Jan 18 at 12:09
$begingroup$
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
Jan 18 at 12:09
2
2
$begingroup$
Yes, coud use that or something like sodium dihydrogen phosphate.
$endgroup$
– Waylander
Jan 18 at 12:36
$begingroup$
Yes, coud use that or something like sodium dihydrogen phosphate.
$endgroup$
– Waylander
Jan 18 at 12:36
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.
Jan 18 at 23:50
$begingroup$
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♦
Jan 18 at 23:55