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The prefixes ortho, meta, and para are all derived from Greek, meaning correct, following, and beside, respectively. The relationship to the current meaning is perhaps not obvious. The ortho description was historically used to designate the original compound, and an isomer was often called the meta compound.
There are 2 ortho positions, 2 meta positions and 1 para position on benzene when a group is attached to it. When a group is an ortho / para director with ortho and para positions reacting with the same partial rate factor, we would expect twice as much ortho product as para product due to this statistical effect.
Although discussions of directing groups usually focus on electronic effects (e.g. EWG vs EDGs), steric effect can prove influential. Thus, nitration of toluene gives approximately 2:1 ortho vs para-nitrotoluene. In the case of tert-butylbenzene, however, the selectivity is reversed:73% of the product is 4-nitro-tert-butybenzene]]. [4]
There are three forms of cresol: ortho-cresol (o-cresol), meta-cresol (m-cresol), and para-cresol (p-cresol). These forms occur separately or as a mixture, which can also be called cresol or more specifically, tricresol. [citation needed] About half of the world's supply of cresols are extracted from coal tar.
Upon reacting, substituents will be added at the ortho, para or meta positions, depending on the directivity of the current substituents to make more complex benzene derivatives, often with several isomers. Electron flow leading to re-aromatization is key in ensuring the stability of such products. [9]
The ortho effect also occurs when a meta-directing group is positioned in a meta arrangement relative to an ortho–para-directing group, a new substituent introduced into the molecule tends to preferentially occupy the ortho position relative to the meta-directing group rather than the para position.
Diethylbenzenes arise as side-products of the alkylation of benzene with ethylene, which can be described as two steps. The first step is the industrial route to ethylbenzene, which is produced on a large scale as a precursor to styrene. C 6 H 6 + C 2 H 4 → C 6 H 5 C 2 H 5. The diethylbenzene is an inadvertent side product. C 6 H 5 C 2 H 5 ...
Since "normal" room-temperature hydrogen is a 3:1 ortho:para mixture, its molar residual rotational energy at low temperature is (3/4) × 2Rθ rot ≈ 1091 J/mol, [citation needed] which is somewhat larger than the enthalpy of vaporization of normal hydrogen, 904 J/mol at the boiling point, T b ≈ 20.369 K. [10] Notably, the boiling points of ...