Benzylechloride can be prepared from toluen by chlorination with-?
1. NaOCl
2.SOCl2
3.SO2Cl2
4.None of these
Answer:
The "textbook" way to chlorinate the alpha position of toluene is with chlorine and some UV irradiation at low temperatures.
However, if you actually look in the literature you'll find that sulfuryl chloride (SO2Cl2) has been used also -- under photolytic conditions. There are several papers and patents on it.
If you chlorinate toluene with SOCl2 or SO2Cl2, you chlorinate the aromatic nucleus. You can obtain benzylechloride using UV radiation in presence of FeCl2. NaOCl is used to substitute H with Cl, but on the aromatic nucleus
As mentioned previosuly #1 NaOCl would work to substitue a H with a Cl with most alkyl compounds but not aromatic ones so that is obviously wrong. Reagents for # 2 and #3 would add to the aromatic compound but not in the desired spot for benzyl chloride but instead in the ortho and para postions of the aromatic compund because the CH3 group on the aromatic ring is an activating group and activates the ring for the Cl to add into those 3 diffenrent positions; Also those reagents could (not very likely and depending on conditions) cause mulitple substituions so they are wrong as well. So D is your answer.
In order to add the Chlorine to the structure in the desired spot as mentioned above all you need to do is chlorinate the toulene with UV light to start a radical reaction. In fact you really don't even need to use the catalyst (although you could) because it is not very cost effecient, and the radical will form easily without the catalyst because chlorine is very reactive and the radical will form readily because the radical intermediate is very stable since it will be resonance stabilized and will delocalized around the ring until we get the desired chlorine radical come in and terminate it.
I hope this helps and if have any other organic questions please feel free to contact me.
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2.SOCl2
3.SO2Cl2
4.None of these
Answer:
The "textbook" way to chlorinate the alpha position of toluene is with chlorine and some UV irradiation at low temperatures.
However, if you actually look in the literature you'll find that sulfuryl chloride (SO2Cl2) has been used also -- under photolytic conditions. There are several papers and patents on it.
If you chlorinate toluene with SOCl2 or SO2Cl2, you chlorinate the aromatic nucleus. You can obtain benzylechloride using UV radiation in presence of FeCl2. NaOCl is used to substitute H with Cl, but on the aromatic nucleus
As mentioned previosuly #1 NaOCl would work to substitue a H with a Cl with most alkyl compounds but not aromatic ones so that is obviously wrong. Reagents for # 2 and #3 would add to the aromatic compound but not in the desired spot for benzyl chloride but instead in the ortho and para postions of the aromatic compund because the CH3 group on the aromatic ring is an activating group and activates the ring for the Cl to add into those 3 diffenrent positions; Also those reagents could (not very likely and depending on conditions) cause mulitple substituions so they are wrong as well. So D is your answer.
In order to add the Chlorine to the structure in the desired spot as mentioned above all you need to do is chlorinate the toulene with UV light to start a radical reaction. In fact you really don't even need to use the catalyst (although you could) because it is not very cost effecient, and the radical will form easily without the catalyst because chlorine is very reactive and the radical will form readily because the radical intermediate is very stable since it will be resonance stabilized and will delocalized around the ring until we get the desired chlorine radical come in and terminate it.
I hope this helps and if have any other organic questions please feel free to contact me.
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