Bond angle

Isn't benzene bulkier than those 2 CH3 grps. to cause more bond angle ?
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17 Replies
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Opt
Opt2mo ago
Ok, I'm not one to say this usually, but I do recommend a tiny bit of research before you post a doubt. Google can do wonders.
Say_miracle_shadow
Say_miracle_shadowOP2mo ago
if benzene is bulkier so y the bond angle is lesser as compared to methoxymethane
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Say_miracle_shadow
Say_miracle_shadowOP2mo ago
i searched but it contradicts the relation b/w the bulkiness and bond angle
Prachi
Prachi2mo ago
The second one is an exception where the methyl groups are bulky which causes repulsion between them making the bond angle greater But don't know the correct reason to explain first one
Say_miracle_shadow
Say_miracle_shadowOP2mo ago
what exactly is the exception u r talking about?
Nimboi
Nimboi2mo ago
maybe resonance related reason in phenol, 1 lone pair is in conjugation with the ring in methoxymethane, there's 2 unscattered lone pairs so i guess lonepair-lonepair repulsion causes the higher angle
Say_miracle_shadow
Say_miracle_shadowOP2mo ago
i took H2O for explaining my pt. if lone lone pair repulsion is greater so the effective bond angle b/w COC should decrease
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iSoham
iSoham2mo ago
Methoxymethane is some ether exception iirc
Nimboi
Nimboi2mo ago
oh right hmm
Nimboi
Nimboi2mo ago
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Nimboi
Nimboi2mo ago
yeah this is weird shouldn't the LP-LP interaction be greater than BP-BP interaction, reducing the ether angle instead of increasing it @Opt thoughts?
itsav23
itsav232mo ago
i think it's smthing to do with their hybridisation. Like in methoxymethane, o is sp3 and lp strongly repel ch bond so more bond angle. In phenol o is partially sp2 due to reso toh ussey mabe lp repulsion reduces and bond angle becomes closer to tetrahedral
Opt
Opt2mo ago
Ok, not an amazing explanation on my behalf, and it's sort of unsatisfactory but the only thing I can think of is that in methoxymethane, the compound exists as a superposition of its hyperconjugated structures right? So, there are net δ- charges on the carbons which are repelling each other, thereby increasing bond angle. With phenol, resonating structures have no issue like this because on the other side, H doesn't have any electronic effects going on.
Say_miracle_shadow
Say_miracle_shadowOP2mo ago
a superposition of its hyperconjugated structures means?
iTeachChem
iTeachChem2w ago
we good?

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