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Chemistry-please don't attempt to answer if you don't know what you're talking about!

i need help with this question, elpaw? hornblower? you guys out there.?


1 ) Suggest why aqueous sodium hydroxide has no reaction with ring-substitued aromatic halogen compounds such as C6H5Cl but reacts readily with haloalkanes such as CH3Cl

IS THIS ANYTHING TO DO WITH LOSS OF ELECTRONS?


ok now this is the big cruncher

2 ) Compound L contains 52.2 % Carbon, 2.7 % hyrdrogen and 44.1 % chlorine by mass. When 1g of L was heated with aqueus sodium hydroxide and the resulting solution treated with an excess of dilute nitric acid followed by aq ag nitrate, 0.892g of silver chloride was formed


Deduce the emp formula for L which is also its molecular formula. Suggest three structures for L. Name and outline a mechanism for the reaction of L with aq sodium hyrdroxide

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Reply 1
dazya...you are so rude!! Be grateful for everyone's input!!
Reply 2
Katie Heskins
dazya...you are so rude!! Be grateful for everyone's input!!


but some is not the input i need
Reply 3
DazzYaa13
i need help with this question, elpaw? hornblower? you guys out there.?


1 ) Suggest why aqueous sodium hydroxide has no reaction with ring-substitued aromatic halogen compounds such as C6H5Cl but reacts readily with haloalkanes such as CH3Cl

IS THIS ANYTHING TO DO WITH LOSS OF ELECTRONS?


ok now this is the big cruncher

2 ) Compound L contains 52.2 % Carbon, 2.7 % hyrdrogen and 44.1 % chlorine by mass. When 1g of L was heated with aqueus sodium hydroxide and the resulting solution treated with an excess of dilute nitric acid followed by aq ag nitrate, 0.892g of silver chloride was formed


Deduce the emp formula for L which is also its molecular formula. Suggest three structures for L. Name and outline a mechanism for the reaction of L with aq sodium hyrdroxide


b) 52.2/12 = 4.35
2.7/1 = 2.7
44.1/35.5 = 1.24

4.35 / 1.24 = 3.5
2.7/1.24 = 2.0
1.24/1.24 = 1.0

C3.5H2Cl

And then just normal nucleophilic substitution by the aq NaOH
Reply 4
imasillynarb
b) 52.2/12 = 4.35
2.7/1 = 2.7
44.1/35.5 = 1.24

4.35 / 1.24 = 3.5
2.7/1.24 = 2.0
1.24/1.24 = 1.0

C3.5H2Cl

And then just normal nucleophilic substitution by the aq NaOH


But you can't have 3.5C, so it would have to be C7H4Cl2

Which I've never seen before, looks very odd to me...
Reply 5
imasillynarb
b) 52.2/12 = 4.35
2.7/1 = 2.7
44.1/35.5 = 1.24

4.35 / 1.24 = 3.5
2.7/1.24 = 2.0
1.24/1.24 = 1.0

C3.5H2Cl

And then just normal nucleophilic substitution by the aq NaOH


holy fuck - thank you so you could jst put it as:

no wait your equation is wrong but you helped me out lots

C
52.2/12 = 4.35
H 3.72/1 = 3.72
Cl 44.1/35.5 = 1.24

Hence C 3.50, H 2,99 and CL 1


Therefore C7H6Cl2

then the mechanisms?
Reply 6
Helenia
But you can't have 3.5C, so it would have to be C7H4Cl2

Which I've never seen before, looks very odd to me...


no H6
Reply 7
DazzYaa13
i need help with this question, elpaw? hornblower? you guys out there.?


1 ) Suggest why aqueous sodium hydroxide has no reaction with ring-substitued aromatic halogen compounds such as C6H5Cl but reacts readily with haloalkanes such as CH3Cl

IS THIS ANYTHING TO DO WITH LOSS OF ELECTRONS?


ok now this is the big cruncher

2 ) Compound L contains 52.2 % Carbon, 2.7 % hyrdrogen and 44.1 % chlorine by mass. When 1g of L was heated with aqueus sodium hydroxide and the resulting solution treated with an excess of dilute nitric acid followed by aq ag nitrate, 0.892g of silver chloride was formed


Deduce the emp formula for L which is also its molecular formula. Suggest three structures for L. Name and outline a mechanism for the reaction of L with aq sodium hyrdroxide
For 1, look up about the electron ring in benzene. I can't remember off-hand why.

2 is easier: Ar of C, H and Cl are 12,1 and 35.5 respectively. Make up a table:

C H Cl
% 52.2 2.7 44.1
Ar 12 1 35.5
%/Ar 4.35 : 2.7 : 1.24
Ratio 3.5: 2 : 1
Thus 7 : 4 : 2

C7H4Cl2

Then again, that isn't very nice.
Reply 8
Helenia
But you can't have 3.5C, so it would have to be C7H4Cl2

Which I've never seen before, looks very odd to me...


It's better known as toothpaste I think :confused: :rolleyes: :biggrin:
Reply 9
DazzYaa13
holy fuck - thank you so you could jst put it as:

no wait your equation is wrong but you helped me out lots

C
52.2/12 = 4.35
H 3.72/1 = 3.72
Cl 44.1/35.5 = 1.24

Hence C 3.50, H 2,99 and CL 1


Therefore C7H6Cl2

then the mechanisms?


You sad H = 2.7 ? :frown:

Helenia: Yeh I thought that was weird as well but it wanted emprical...you cant simply multiply it by 2 as then it isnt the simplest ratio is it?
Reply 10
DazzYaa13
i need help with this question, elpaw? hornblower? you guys out there.?


1 ) Suggest why aqueous sodium hydroxide has no reaction with ring-substitued aromatic halogen compounds such as C6H5Cl but reacts readily with haloalkanes such as CH3Cl

IS THIS ANYTHING TO DO WITH LOSS OF ELECTRONS?


ok now this is the big cruncher

2 ) Compound L contains 52.2 % Carbon, 2.7 % hyrdrogen and 44.1 % chlorine by mass. When 1g of L was heated with aqueus sodium hydroxide and the resulting solution treated with an excess of dilute nitric acid followed by aq ag nitrate, 0.892g of silver chloride was formed


Deduce the emp formula for L which is also its molecular formula. Suggest three structures for L. Name and outline a mechanism for the reaction of L with aq sodium hyrdroxide


1) This is to do with the negative inductive effect of the benzene ring. Basically the benzene ring draws electrons away from the polar C -- Cl bond, making it less polar and thus less susceptible to nucleophilic attack. As sodium hydroxide is presemably acting as a nucleophile (through nucleophilic substitution) it will react and displace the d+ chlorine in chloromethane, but not the less polar chlorine atom in chlorobenzene.
Reply 11
so then 1 g gives 0.982g AgCl = 0.982 / 143.5 which = 6.84 x 10^-3 mol
Reply 12
imasillynarb
You sad H = 2.7 ? :frown:

Helenia: Yeh I thought that was weird as well but it wanted emprical...you cant simply multiply it by 2 as then it isnt the simplest ratio is it?

Yes, because it's the simplest whole number ratio. I'd argue that Helenia's ratio is simpler (and also it says the empirical is the same as the molecular, which can't be the case if you have C3.5.)
Reply 13
boygenious
1) This is to do with the negative inductive effect of the benzene ring. Basically the benzene ring draws electrons away from the polar C -- Cl bond, making it less polar and thus less susceptible to nucleophilic attack. As sodium hydroxide is presemably acting as a nucleophile (through nucleophilic substitution) it will react and displace the d+ chlorine in chloromethane, but not the less polar chlorine atom in chlorobenzene.


omgosh thank you
Reply 14
DazzYaa13
so then 1 g gives 0.982g AgCl = 0.982 / 143.5 which = 6.84 x 10^-3 mol


Didnt ask for that though did it?
Reply 15
meepmeep
Yes, because it's the simplest whole number ratio. I'd argue that Helenia's ratio is simpler (and also it says the empirical is the same as the molecular, which can't be the case if you have C3.5.)


Oh, its the simplest whole number ratio? I just thought it was the simplest ratio :frown:
Reply 16
DazzYaa13
omgosh thank you


no prob.
Reply 17
imasillynarb
Didnt ask for that though did it?


i did it just incase - the question is worth a lot of marks
Reply 18
1 is easy, ring compund don't react redily because of the close structure, it's bonded with all C bonds, where as a zig zag structure, it's more opened
Reply 19
can't believe ure all discussing chemistry and formula's at nearly 4am :eek:

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