3- Methylpentane, products from

Proportions of Isotopically Labeled Products from Isomerization of 2-Methylpentane-2-13C over Thick... 

Product from 2-methylpentane over film catalysts also contain up to 1% 2,3-dimethylbutane. 

Treatment of (2i ,3 )-2-bromo-3-methylpentane with sodium ethoxide in ethanol gives (ii)-3-methylpent-2-ene as the major product. What would be the major product from similar base treatment of (23, 33 )- and 2R,3S)-2-bromo-3-methylpentane Hint Newman projections will be useful here. 

The major products from similar base treatment of (2S,3S)- and (2/f,36 )-2-bromo-3-methylpentane can be deduced as below... 

The hydroformylation of several olefins in the presence of Co2(CO)8 under high carbon monoxide pressure is reported. (S)-5-Methylheptanal (75%) and (S)-3-ethylhexanal (4.8%) were products from (- -)(S)-4-methyl-2-hexene with optical yields of 94 and 72%, respectively. The main products from ( -)(8)-2,2,5-trimethyl-3-heptene were (S)-3-ethyl-6,6-di-methylheptanal (56.6%) and (R)-4,7,7-trimethyloctanal (41.2%) obtained with optical yields of 74 and 62%, respectively. (R)(S)-3-Ethyl-6,6-dimethylheptanal (3.5% ) and (R)(S)-4,7,7-trimethyloctanal (93.5%) were formed from (R)(S)-3,6,6-trimethyl-l-heptene. (+/S)-l-Phenyl-3-methyl-1-pentene, under oxo conditions, was almost completely hydrogenated to (- -)(S)-l-phenyl-3-methylpentane with 100% optical yield. 3-(Methyl-d3)-l-butene-4-d3 gave 4-(methyl-d3)pentarwl-5-d3 (92%), 2-methyl-3-(methyl-d3)-butanal-4-d3 (3.7%), 3-(methyl-d3)pentanal-2-d2,3-d1 (4.3%) with practically 100% retention of deuterium. The reaction mechanism is discussed on the basis of these results. 

Perfluoro(2-methylpropene) is the product of the pyrolysis of perfluoro(2-iodo-2-methylpropane) at 300°C in a platinum vessel.194 Perfluoro(4-methylpent-l-ene) was obtained as a minor product from perfluoro(l-iodo-4-methylpentane) in dimethylformamide at 80 C.195... 

Relative hydrogen transfer activity can be determined using an HTI test (11), where the index is a measure of the degree of saturation in the reaction product. The test determines the product ratio of 3-methylpentenes to 3-methylpentane derived from a 1-hexene feed. While the branched products come mainly from oligomerization followed by cracking, the results should be relevant here as well. The higher the index, the lower the relative hydrogen transfer activity. 

Using Table III in Ref. 68 (p. 692), calculate the expected product composition from the gas-phase photochemical chlorination and bromination of 3-methylpentane under conditions (excess hydrocarbon) in which only monohalogenation would occur. 

Problem 10.3 Draw and name all monochloro products you would expect to obtain from radical chlorination of 2-methylpentane. Which, if any, are chiral ... 

Solutions in organic solvents may, with certain reservations, be used directly, provided that the viscosity of the solution is not very different from that of an aqueous solution. The important consideration is that the solvent should not lead to any disturbance of the flame an extreme example of this is carbon tetrachloride, which may extinguish an air-acetylene flame. In many cases, suitable organic solvents [e.g. 4-methylpentan-2-one (methyl isobutyl ketone) and the hydrocarbon mixture sold as white spirit ] give enhanced production of ground-state gaseous atoms and lead to about three times the sensitivity... 

Referring first of all to the reactions over 0.2% platinum/alumina (Table V) the major features of the product distributions may be explained by a simple reaction via an adsorbed C5 cyclic intermediate. For instance, if reaction had proceeded entirely by this path, 2-methylpentane-2-13C would have yielded 3-methylpentane labeled 100% in the 3-position (instead of 73.4%) and would have yielded n-hexane labeled 100% in the 2-position (instead of 90.2%). Similarly, 3-methylpentane-2-I3C would have yielded a 2-methylpentane labeled 50% in the methyl substituent (instead of 42.6%), and would have yielded n-hexane labeled 50% in the 1- and 3-positions (instead of 43.8 and 49% respectively). The other expectations are very easily assessed in a similar manner. On the whole, the data of Table V lead to the conclusion that some 80% or so of the reacting hydrocarbon reacts via a simple one step process via an adsorbed C5 cyclic intermediate. The departures from the distribution expected for this simple process are accounted for by the occurrence of bond shift processes. It is necessary to propose that more than one process (adsorbed C6 cyclic intermediate or bond shift) may occur within a single overall residence period on the catalyst Gault s analysis leads to the need for a maximum of three. The number of possible combinations is large, but limitations are imposed by the nature of the observed product distributions. If we designate a bond shift process by B, and passage via an adsorbed Cs cyclic intermediate by C, the required reaction paths are... 

Unlike the behavior over 0.2% platinum/alumina, the main features of the labeled product distributions obtained over 10% platinum/alumina and over platinum film catalysts (Tables VI and VII respectively) cannot be explained in terms of a single dominant reaction pathway via an adsorbed C6 cyclic intermediate. Again, parallel, multiple-step reaction pathways are involved. The results from 2-methylpentane-2-13C have been qualitatively accounted for (84) by the pathways... 

These cycloadducts, at their most elementary level, are excellent intermediates for the synthesis of 3-substituted furan derivatives. For example, Kawanisi and coworkers reported a synthesis of perillaketone 174 in which the critical step was a Paterno-BUchi photocycloaddition between furan and 4-methylpentanal in the presence of methanesul-fonic acid (Scheme 39)82. This reaction furnished two initial photoadducts, 172 and 173. The unexpected product 173 presumably arises from a Norrish Type II cleavage of 4-methylpentanal to give acetaldehyde, and subsequent cycloaddition with furan. The desired cycloadduct 172 was then converted uneventfully to 174 via acid-catalyzed aromatization and oxidation. 

The reactivity between a tertiary C-H site and a sterically accessible, secondary C-H site is relatively even in the reactions catalyzed by TpBf3Cu. This can be seen in the reaction with 2-methylpentane (Equation (7)),38,49,56 which gave rise to a mixture of only two products. No insertion into the methyl or the sterically crowded methylene C-H bonds was seen. The C-H insertion has the possibility of selectively functionalizing relatively complex alkanes. An impressive example is the C-H insertion to 1 (Equation (8)).56 A mixture of two alkylation products derived from insertion at the tertiary C-H bonds was obtained. This transformation has been extended to the selective functionalization of hydrocarbon polymers.75... 

Hexanc is a very volatile aliphatic hydrocarbon. It is a constituent in the paraffin fraction of crude oil and natural gas and is also used as an industrial chemical and laboratory reagent. Laboratory grade -hexane contains approximately 99% w-hexane. "Hexane" or "hexanes" is a commercial and industrial product consisting of a mixture of hydrocarbons with six carbon atoms and includes -hexane and its isomers 2-methylpentane and 3-methylpentane as well as small amounts of other hydrocarbons (Brugnone et al. 1991). Laboratory and industrial solvents such as "hexane" and petroleum ether contain -hexane from <0.1% to as much as 33% (Creaser et al. 1983). Information regarding the chemical identity of -hexane is located in Table 3-1. 

Rhodium-phosphine catalysts are unable to hydroformylate internal olefins, so much that in a mixture of butenes only the terminal isomer is transformed into valeraldehydes (see 4.1.1.2). This is a field still for using cobalt-based catalysts. Indeed, [Co2(CO)6(TPPTS)2] -i-lO TPPTS catalyzed the hydroformylation of 2-pentenes in a two-phase reaction with good yields (up to 70%, but typically between 10 and 20 %). The major products were 1-hexanal and 2-methylpentanal, and n/i selectivity up to 75/25 was observed (Scheme 4.12). The catalyst was recycled in four mns with an increase in activity (from 13 to 19 %), while the selectivity remained constant (n/i = 64/36). 

The data in Table 7 show that the selectivity for 2-oxygenated products in the oxidation of alkanes on TS-1 is somewhat higher than could be expected on statistical grounds. Only for 3-methylpentane, this selectivity becomes overcompensated by the higher reactivity of tertiary C-H compared to secondary C-H positions. This indicates that the first step of the oxidation, i.e. the formation of alcohols from alkanes is slightly regioselective. Within the ketone fraction, the selectivity for 2-ketones is even more pronounced, indicating that 2-alcohols are selectively oxidized to 2-ketones in the... 

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