Please help, Organic chemistry :/
Hey, can you please help me? Please rank these in order ofacidity, starting with the most acidic to the lease acidic and explain please. CH3COOHHCLC6 H5OHC3H7OHH2O I know it’s HCL then CH3COOH but I can’t figure out therest. Can you explain in terms of alkyl groups pushing electrons and making thecompound more/less stable and in terms of electron rings in benzene making thecompound more/less stable. Thanks
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Original post by DonatKap14
Hey, can you please help me? Please rank these in order ofacidity, starting with the most acidic to the lease acidic and explain please. CH3COOHHCLC6 H5OHC3H7OHH2O I know it’s HCL then CH3COOH but I can’t figure out therest. Can you explain in terms of alkyl groups pushing electrons and making thecompound more/less stable and in terms of electron rings in benzene making thecompound more/less stable. Thanks
I would answer you directly but chances are I'm going to make the same mess you've made with the formulae (would it kill you to use a comma?) and won't explain it very well. Here's a great website to learn more about this (and about high school chemistry in general):
http://www.chemguide.co.uk/basicorg/acidbase/acids.html#top
(edited 8 years ago)
First of all can you define acidity? You need to consider the factors that affect the strength of an acid (HINT: Consider the stability of the conjugate base). When it comes to ranking the order of stability, nucleophilicity, basicity etc.. it's all about being able to define the key term, stating what affects it and how the compounds you've been presented with relate to this.
CH3COOH, HCL, C6 H5OH, C3H7OH, H2O
I know it’s HCL then CH3COOH but I can’t figure out the rest. Can you explain in terms of alkyl groups pushing electrons and making the compound more/less stable and in terms of electron rings in benzene making the compound more/less stable. Thanks
@Hydeman haha sorry, I copied that from Ms Word and forgot to preview it. So from the link you gave me. the easier is at releasing hydrogen, the more acidic it is. HCL and ehtanoic acid are the only acids here, HCLis the most acidic since it's a strong acid while ethanoic acid is a weak acid, which comes second. On number 3 we have phenol because once it releases the hydrogen, the compound it forms is more stable/less likely to react again with the hydrogen compared to propanoI (WHY IS THE COMPOUND MORE STABLE?think the author of that page made a mistake when explaining the phenol part). Though I know propanol's compound is less stable because once it loses the hydrogen, the negative charge is spread over only the oxygen atom, making it likely to attract the hydrogen again (so it's bad at losing hydrogen). so we have propanol at number 5. and at 4 we have water, i would say because it's neutral?
so from most reactive to least: HCL, CH3COOH, C6H5OH, H2O, C3H7OH
Can you confirm? anything i missed? please clarify the explanations for water and pehnol
I know it’s HCL then CH3COOH but I can’t figure out the rest. Can you explain in terms of alkyl groups pushing electrons and making the compound more/less stable and in terms of electron rings in benzene making the compound more/less stable. Thanks
@Hydeman haha sorry, I copied that from Ms Word and forgot to preview it. So from the link you gave me. the easier is at releasing hydrogen, the more acidic it is. HCL and ehtanoic acid are the only acids here, HCLis the most acidic since it's a strong acid while ethanoic acid is a weak acid, which comes second. On number 3 we have phenol because once it releases the hydrogen, the compound it forms is more stable/less likely to react again with the hydrogen compared to propanoI (WHY IS THE COMPOUND MORE STABLE?think the author of that page made a mistake when explaining the phenol part). Though I know propanol's compound is less stable because once it loses the hydrogen, the negative charge is spread over only the oxygen atom, making it likely to attract the hydrogen again (so it's bad at losing hydrogen). so we have propanol at number 5. and at 4 we have water, i would say because it's neutral?
so from most reactive to least: HCL, CH3COOH, C6H5OH, H2O, C3H7OH
Can you confirm? anything i missed? please clarify the explanations for water and pehnol
Original post by DonatKap14
CH3COOH, HCL, C6 H5OH, C3H7OH, H2O
I know it’s HCL then CH3COOH but I can’t figure out the rest. Can you explain in terms of alkyl groups pushing electrons and making the compound more/less stable and in terms of electron rings in benzene making the compound more/less stable. Thanks
@Hydeman haha sorry, I copied that from Ms Word and forgot to preview it. So from the link you gave me. the easier is at releasing hydrogen, the more acidic it is. HCL and ehtanoic acid are the only acids here, HCLis the most acidic since it's a strong acid while ethanoic acid is a weak acid, which comes second. On number 3 we have phenol because once it releases the hydrogen, the compound it forms is more stable/less likely to react again with the hydrogen compared to propanoI (WHY IS THE COMPOUND MORE STABLE?think the author of that page made a mistake when explaining the phenol part). Though I know propanol's compound is less stable because once it loses the hydrogen, the negative charge is spread over only the oxygen atom, making it likely to attract the hydrogen again (so it's bad at losing hydrogen). so we have propanol at number 5. and at 4 we have water, i would say because it's neutral?
so from most reactive to least: HCL, CH3COOH, C6H5OH, H2O, C3H7OH
Can you confirm? anything i missed? please clarify the explanations for water and pehnol
I know it’s HCL then CH3COOH but I can’t figure out the rest. Can you explain in terms of alkyl groups pushing electrons and making the compound more/less stable and in terms of electron rings in benzene making the compound more/less stable. Thanks
@Hydeman haha sorry, I copied that from Ms Word and forgot to preview it. So from the link you gave me. the easier is at releasing hydrogen, the more acidic it is. HCL and ehtanoic acid are the only acids here, HCLis the most acidic since it's a strong acid while ethanoic acid is a weak acid, which comes second. On number 3 we have phenol because once it releases the hydrogen, the compound it forms is more stable/less likely to react again with the hydrogen compared to propanoI (WHY IS THE COMPOUND MORE STABLE?think the author of that page made a mistake when explaining the phenol part). Though I know propanol's compound is less stable because once it loses the hydrogen, the negative charge is spread over only the oxygen atom, making it likely to attract the hydrogen again (so it's bad at losing hydrogen). so we have propanol at number 5. and at 4 we have water, i would say because it's neutral?
so from most reactive to least: HCL, CH3COOH, C6H5OH, H2O, C3H7OH
Can you confirm? anything i missed? please clarify the explanations for water and pehnol
Yes, you've got it right.
For phenol, the reason it dissociates (loses the hydrogen to form ions) easily in solution is because the O-H bond is weakened due to the incorporation of a p-orbital from the oxygen atom into the delocalised pi-electron ring system of the benzene ring. When this happens, the resulting negative charge on the oxygen atom is delocalised around the benzene ring (which includes a p-orbital from the oxygen atom, as mentioned previously), making the phenoxide ion (that's the benzene ring with only an oxide ion attached) more stable than phenol itself. So the negative charge is evenly spread across several of the atoms instead of being concentrated on the oxygen atom and that's why it's more stable.The explanation for water is slightly harder to put... What you could say is that the reason ethanol is less acidic than water is because the ethoxide ion (negative ion formed after H+ is lost) is less stable than the ethanol molecule as the charge is not delocalised across several atoms as it is in carboxylate ions and the phenoxide ion. For A-level you just need to know that water has a pH of around 7 and that ethanol is less acidic than that for the reasons discussed.
(edited 8 years ago)
Excellent explanation! Thank you so much
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