[beheada]

The problem:

CH₃Cl + NaOH ----> CH₃OH + NaCl

I am drawing the entire structures, with all valence electrons and curved arrows for electron flow. I think I might be criss-crossing some wires, but this is what I've come up with. The Cl attached to Carbon is partially negative due to electronegativity, which makes the carbon partially positive. The oxygen molecule is partially negative due to the same reasoning, making Na and H both partially positive. Where I'm stupified, is how to draw the arrows, since both the Cl-C bond and Na-O bond need to break. My conclusion is that the Cl-C electron pair goes to Chlorine, making it a Cl^- ion and making the Carbon positive. Then the Na-O bond goes to the oxygen, making it negative. Now the Cl^- nabs the Na ionically and then the Oxygen bonds with Carbon.

Does this describe what actually happens? If so, how do I tell which molecule is a nucleophile vs. electrophile, since the Cl acts as a nucleophile and the Na acts as an electrophile... BUT... the Oxygen also acts as a nucleophile and the carbon as an electrophile? Someone clarify?


rayfe

[Borek]

NaOH? Are we talking about solids?

[beheada]

I assumed that carried no relevance. There is nothing in the problem indicating which phase the structures are in.

[AWK]

The problem:

CH₃Cl + NaOH ----> CH₃OH + NaCl

I am drawing the entire structures, with all valence electrons and curved arrows for electron flow. I think I might be criss-crossing some wires, but this is what I've come up with. The Cl attached to Carbon is partially negative due to electronegativity, which makes the carbon partially positive. The oxygen molecule is partially negative due to the same reasoning, making Na and H both partially positive. Where I'm stupified, is how to draw the arrows, since both the Cl-C bond and Na-O bond need to break. My conclusion is that the Cl-C electron pair goes to Chlorine, making it a Cl^- ion and making the Carbon positive. Then the Na-O bond goes to the oxygen, making it negative. Now the Cl^- nabs the Na ionically and then the Oxygen bonds with Carbon.

Does this describe what actually happens? If so, how do I tell which molecule is a nucleophile vs. electrophile, since the Cl acts as a nucleophile and the Na acts as an electrophile... BUT... the Oxygen also acts as a nucleophile and the carbon as an electrophile? Someone clarify?


rayfe

See SN₂ mechamism in organic textbooks

[beheada]

I'm assuming you're talking about S_n2 reaction (at least that's the way I found it in the text). Along those lines, the reaction proceeds as follows... (correct me if I'm wrong):

We know that the Sodium is ionically bonded to the hydroxy group.
The OH attacks the partially positive carbon of the alkyl halide and boots the halogen, by breaking the C-Cl bond.
The halogen then ionically bonds with Sodium.

rayfe

[AWK]

Yes, this is an explanation. One bond is broken (C-Cl) , one bond is formed (HO-C)