# Tag Info

3

I appreciate Waylander's answer. However, although the answer gives you the basic mechanisms for Reimer–Tiemann and Kolbe-Schmidt reactions, it does not address some question and OP's misconceptions such as: The $\ce{CO2}$ liberated will react with the phenol. Thus, I'd like to address these by using the same starting materials used in the question. ...

2

The acid strength of each compound can be explained, but the acidity order is much more difficult to compare, because the two compounds are only remotely connected. It is misleading to conclude that the mere presence of a phenyl group somehow connects these molecules. The similarity of the pK$_a$s is likely a coincidence. The question needs a clear ...

3

This is the mechanism of the Reimer-Tiemann reaction (source Wikipedia here) The polyhaloform reacts with strong base to create a carbene, a highly reactive species which reacts with the phenoxide anion through the alpha carbon to give an anionic intermediate with the -ve charge on the halogenated carbon. It is this species that picks up the deuterium. In ...

4

@Harry Holmes: Here is a simplified example of how the formation of Bakelite may occur under base-catalyzed conditions to incorporate formaldehyde as -CH2- at the ortho and para positions of phenol. There are a myriad of permutations as to the order of condensations. I have selected one that illustrates the Michael-like addition that seems to have eluded you....

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For alkyl groups attached to the phenol ring, there are two main points that your reasoning does not take account of - Inductive effect is distance dependent. As the distance increases, its effect becomes very small. Even if the group were near, the general trend is that hyperconjugation has stronger effect than inductive effect. You can refer the ...

3

The reason provided by ML cannot explain the difference in acidities since the +I effect doesn't come into play normally for the para positions. A more likely reason is hyperconjugation (or no bond resonance) where the number of hydrogens directly attached to the benzyl carbon decreases as it goes from P to S. This means that the number of destabilizing ...

1

Taken from my answer here: Comparing methane and acetylene shows a difference of $\approx 20$ $\mathrm pK_\mathrm a$ units Comparing $\mathrm p K_\mathrm a$ of phenol($10.0$) and methanol($15.5$), we see that the presence of one resonating ring only produces a 5.5 $\mathrm p K_\mathrm a$ difference. Resonance in triphenyl system is effectively only one ...

0

Phenol is C6H6O, essentially adding one oxygen atom to benzene. The cumene process allows the sharing of two oxygen atoms between benzene and propene and make phenol and acetone. Similarly the similar process by Exxon-Mobil allows the sharing between benzene and cyclohexane which is produced by hydrogenation of benzene. Therefore, I think the readers can see ...

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