This page gives you the facts and a simple, uncluttered mechanism for the free radical substitution reaction between methane and bromine. This reaction between methane and bromine happens in the presence of ultraviolet light - typically sunlight. This is a good example of a photochemical reaction - a reaction brought about by light. The organic product is bromomethane. One of the hydrogen atoms in the methane has been replaced by a bromine atom, so this is a substitution reaction.

However, the reaction doesn't stop there, and all the hydrogens in the methane can in turn be replaced by bromine atoms. The mechanism involves a chain reaction. During a chain reaction, for every reactive species you start off with, a new one is generated at the end - and this keeps the process going. The over-all process is known as free radical substitution, or as a free radical chain reaction.

Br 2 2Br. Jim Clark Chemguide. A Free Radical Substitution Reaction This page gives you the facts and a simple, uncluttered mechanism for the free radical substitution reaction between methane and bromine.

The mechanism The mechanism involves a chain reaction. Chain initiation: The chain is initiated started by UV light breaking a bromine molecule into free radicals.

Br 2 2Br Chain propagation reactions: These are the reactions which keep the chain going. Contributors Jim Clark Chemguide.It is one of several isomers of octane C 8 H This particular isomer is the standard point on the octane rating scale the zero point is n -heptane.

It is an important component of gasolinefrequently used in relatively large proportions to increase the knock resistance of the fuel.

However, 2,2,4-trimethylpentane is by far the most important isomer of octane and so, historically, it has been assigned this name. Isooctane is produced on a massive scale in the petroleum industry by alkylation of isobutene with isobutane. The process is conducted in alkylation units in the presence of acid catalysts.

monobromination of pentane

It can also be produced from isobutylene by dimerization using an Amberlyst catalyst to produce a mixture of iso-octenes. Hydrogenation of this mixture produces 2,2,4-trimethylpentane. Engine knocking is an unwanted process that can occur during high compression ratios in internal combustion engines. Graham Edgar in added different amounts of n -heptane and 2,2,4-trimethylpentane to gasoline, and discovered that the knocking stopped when 2,2,4-trimethylpentane was added.

This work was the origin of the octane rating scale. The same test motors, run in the same fashion, using heptane, gave a performance which was standardized as 0 octane. All other compounds and blends of compounds then were graded against these two standards and assigned octane numbers.

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In common with all hydrocarbons, 2,2,4-trimethylpentane is flammable. From Wikipedia, the free encyclopedia. Redirected from Isooctane. Chemical compound.

CAS Number. Interactive image. Beilstein Reference. PubChem CID. Chemical formula. Refractive index n D. Heat capacity C. Std molar entropy S o GHS hazard statements.

GHS precautionary statements. Autoignition temperature. PubChem Compound. Identification and Related Records. Retrieved 11 March Ullmann's Encyclopedia of Industrial Chemistry.

Weinheim: Wiley-VCH.

Making a Bromoalkane (1-bromopentane - NaBr/H2SO4 Method)

Organic chemistry Reprinted with corrections. Oxford [u. Vora; Joseph A. Kocal; Paul T.By using our site, you acknowledge that you have read and understand our Cookie PolicyPrivacy Policyand our Terms of Service.

Chemistry Stack Exchange is a question and answer site for scientists, academics, teachers, and students in the field of chemistry. It only takes a minute to sign up. My organic chemistry final is next Tuesday, and I have worked through the practice final.

The last question is the following: Give and name all the compounds resulting from the radical monobromination 2,3-dimethylpentane. Indicate the major and minor products. I can clearly see my chiral centres, but how do I determine the orientation of the H?

Red is the major product, blue is the minor product, and magenta is the very minor product. The second question is: write the mechanism of this reaction identifying the initiation, propagation, and termination steps for the formation of one of the products.

This is what I drew:. My prof says that I am missing a propagation step with another bromine-bromine molecule. I would greatly appreciate your input! All you need to show is the organic radical reacting with diatomic bromine to form you brominated molecule and another bromine radical. Sign up to join this community. The best answers are voted up and rise to the top.

Home Questions Tags Users Unanswered. Products of radical bromination and mechanism Ask Question. Asked 4 years, 10 months ago. Active 2 years ago. Viewed 3k times. This is what I drew: My prof says that I am missing a propagation step with another bromine-bromine molecule.

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Johnathan Johnathan 3 3 silver badges 9 9 bronze badges. Active Oldest Votes. That's what I thought. Your starting material is chiral, and all of the products will chiral.

Dec 11 '15 at I have edited my question: I can see it now. The molecules have either 1 or 2 chiral centres.Neopentanealso called 2,2-dimethylpropaneis a double-branched-chain alkane with five carbon atoms.

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Neopentane is a flammable gas at room temperature and pressure which can condense into a highly volatile liquid on a cold day, in an ice bath, or when compressed to a higher pressure. Neopentane is the simplest alkane with a quaternary carbonand has achiral tetrahedral symmetry. It is one of the three structural isomers with the molecular formula C 5 H 12 pentanesthe other two being n -pentane and isopentane. Out of these three, it is the only one to be a gas at standard conditions; the others are liquids.

The traditional name neopentane was still retained in the IUPAC recommendations, [4] [5] but is no longer recommended according to the recommendations. As Np also symbolises the element neptunium atomic number 93 one should use this abbreviation with care. The obsolete name tetramethylmethane is also used, especially in older sources.


The boiling point of neopentane is only 9. Therefore, neopentane is a gas at room temperature and atmospheric pressure, while the other two isomers are barely liquids. This anomaly has been attributed to the better solid-state packing assumed to be possible with the tetrahedral neopentane molecule; but this explanation has been challenged on account of it having a lower density than the other two isomers.

Moreover, its enthalpy of fusion is lower than the enthalpies of fusion of both n -pentane and isopentane, thus indicating that its high melting point is due to an entropy effect resulting from higher molecular symmetry. Indeed, the entropy of fusion of neopentane is about 4 times lower than that of n -pentane and isopentane.

The symmetry of the neopentane molecule can be broken if some hydrogen atoms are replaced by deuterium atoms. In particular, if each methyl group has a different number of substituted atoms 0, 1, 2, and 3one obtains a chiral molecule. The chirality in this case arises solely by the mass distribution of its nuclei, while the electron distribution is still essentially achiral.

From Wikipedia, the free encyclopedia. Neopentane Tetramethylmethane [1]. CAS Number. Interactive image. Beilstein Reference. Gmelin Reference. PubChem CID. Chemical formula. Heat capacity C. Std molar entropy S o Thermal and Vapor Pressure Data for Tetramethylmethane from Please complete any questions as much as you can before posting. It is OK if you are a little or a lot! It is also important that you describe the specific part of the problem you are struggling with.

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How many sterioisomers can be obtained from the monobromination of Pentane? What are the three you're thinking of? I can only think of two, assuming we're talking about n-pentane. Your question specifically asks for stereo-isomers, and since pentane is saturated and therefore doesn't exhibit E-Z or cis-trans isomerism, the only other type of stereoisomerism is optical isomerism.

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Therefore it must be looking for optical isomers. But if you attach the bromine to carbon 3, then there are now two ethyl groups attached to carbon 3 so there are no longer optical isomers since there aren't 4 different groups attached to the same carbon atom!

A good hint that your answer of 3 is wrong would be the fact that optical isomers must come in pairs enantiomers so there must be an even number. If the question asked how many structural isomers can be obtained, then your answer would be correct. However, I don't know what level of chemistry you are at, so feel free to ask for further information. A good hint that your answer of 3 is wrong would be the fact that optical isomers must come in pairs enantiomers.

Ah thanks for that information - we don't learn about meso compounds on my syllabus, but it was interesting to find out about! As you can see, 2 has four different substituents. What is your conclusion about this fact? Essentially the consequences on stereoisomers of this molecule? Use of this site constitutes acceptance of our User Agreement and Privacy Policy. All rights reserved.

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Become a Redditor and join one of thousands of communities. I thought 3, but was told 4. What are they?Bailey, In, Berkeley, and Sumner H. McAliister, Lafayette, alif. Application Match 4. The present invention relates to halogenation, via substitution, and more particularly pertains to the eflicient and controlled halo'genation of cyclopentane and of organic compounds containing a cyclopentyl radical. In one of its speciflc embodiments the invention covers a novelprocess for the economic and efilcient halogenation, such-as chlorination, of cyclopentane'or of organic compounds containing a cyclopentyl radical to produce large yields of the desired partially halogenated cyclopentane hydrocarbon.

Although the direct halogenation, via substitution, of various saturated aliphatic hydrocarbons, as well as some of the saturated cyclic compounds, has been known for some time. For ex- I ample, cyclopentyl chloride. Another object is to provide a continuous process whereby the above-outlined and hereinbelow more fully described group of cyclic organic compounds may be efficiently subjected to direct halogenation via substitution, to produce high yields of partially halogenated compounds while at the' same time avoiding, or at least greatly inhibiting side-reactions, such as the formation of 'highly halogenated cyclic compounds.

It has now been discovered that the above and other objects may be attained by subjecting cyclopentane, or organic compounds containing a cyclopentyl radical, to the action of a halogen under certain operating conditions to be described more fully hereinbelow.

It has also been discovered that the above-defined group of saturated cyclic organic compounds may. For instance, Markownikow produced l-chlor-l-methyl cyclopentane by first reacting methyl cyclopentane with nitric acid to form the tertiary nitro-compound, which was then treated with hydrogen to form the corresponding tertiary amino-compound. Clearly, such complicated procedure cannot be profitably employed commercially for the manufacture of halogenated compounds.

It is the main object of the present invention to provide a simple and economic process for the stitution, to obtain certain desired partially hal-v ogenated derivatives thereof, by subjecting the primary material to the direct action of a halo gen under conditions whereby the material to be subjected to halogenation is employed in a large excess over the quantity necessary for reacting with the halogen introduced into the reaction zone, and whereby the product of halo-substitution is withdrawn from the reaction zone substantially as soon as formed.

Representative examples of saturated organic compounds which may be halogenated in accordance with the process of the present invention include cyclopentane, alkylated cyclopentanes, such as methyl cyclopentane, ethyl cyclopentane, 1,2-dim'ethyl cyclopentane, 1,3-dimethyl cyclopentane, cismethylethyl cyclopentane, trans-l-methyl-z-ethyl cyclopentane, lmethylisopropyl cyclopentane, 1,2- dimethyl- 3-isopropyl cyclopropane, and the like, and their homologues arid analogues, and the partially halogenated derivatives of these and similar cyclic compounds containing a cyclopentyl radi.

In accordance with the process of the present ingention, the halogenation may be controlled so as to produce high yields of a given and desired product of halo-substitution, while inhibiting the formation of undesirable highly halogenated derivatives thereof.

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Furthermore, in one of its specific embodiments, the present invention comprises a continuous process for the halogenation, via substitution, of the above-described cyclopentyl hydrocarbons, this process including the steps of continuously conveying halogen with a large excess of the primary cyclic material through the reaction zone to produce partially halo-substituted derivatives of the cyclic com! This may be accomplished by continuously introducing a halogen together with a relatively large excess of the saturated cyclic compound of the described class, such as cyclopentane, into a reaction zone maintained under halosubstitution promoting conditions, and removing the product of halo-substitution, e.

As stated, in order to avoid or minimize the formation of highly halogenated compounds, the reaction mustbe effected in the presence of a large excess of the cyclic organic compound subjected to the treatment. In fact, it was found that the ratio of the primary material to the halogen should. In effecting the halo-substitution reaction in a continuous manner, use may be made of a rectifying column provided with a reaction zone, such column allowing the continuous and substantially immediate withdrawal of the reaction products from the reaction zone, thus avoiding or reducing undesirable side reactions.

The use of such a rectifying column also permits rapid and even substantially immediate removal of the vaporous reactants and reaction products, and the return of the unused reagent or reagents back to the reaction zone, while restricting the halogenation reaction to that zone where optimum conditions of concentration and temperature are maintained.

Also, by heating the reaction products leaving the reaction zone, it is possible to rectify them and return the unreacted fraction back into the reaction zone. It is clear that such a procedure prevents or materially decreases undesirable secondary reactions such as the formation of highly halogenated cyclopentyl radical-containing compounds both in the reaction zone and after withdrawal of the unreacted cyclopentane hydrocarbons and the desired partially halogenated derivatives thereof.

Since the halo-substitution is to be effected with a large excess of the defined organic compound, the unreacted portion thereof, preferably after the removal of the hydrogen halide which is formed as a by-product of the halo-substitution reactionmay be returned back into the aforementioned reaction zone for the purpose of commingling and reacting with additional quantities of halogen introduced thereinto.

Such a. Although, as was brought out above, the novel' process constituting the main object of the present inventionis applicable to the efficient halogenation, via substitution, of a relatively large group of organic saturated compounds containing a cyclopentyl radical, the process is particularly adapted to the halo-substitution of cyclopentane to produce high yields of cyclopentyl halides, while retarding or inhibiting the formation of poly-halide derivatives thereof.

The cyclopentyl halides, such as cyclopentyl chloride, are highly valuable intermediates in the production of cyclopentanol which is extensively and industrially employed, for example, in the manufacture of varnishes.

Therefore, as an example, the present invention will be described with particular reference to the chlorination of cyclopentane, it being understood, however, that these reactions are examples only, that the invention is broadly directed to the controlled halo-substitution of the defined group or class of cyclic organic compounds, and that, therefore, there is no intention of limiting the invention to any particular features described herein, the invention being coextensive in scope with the appended claims.

Example I cyclopentane was subjected to chlorination in an apparatus consisting of a glass packed column superimposed on a kettle provided with heatin means.

What are all of the possible products of monobromination of pentane?

The upper end of the column communicated with a condenser for the liquefaction of the unreacted cyclopentane, and with means for returning this liquid as reflux back into the column. The chlorine was introduced gradually and slowly into the column at an intermediate point therein. During the chlorination reaction the unreacted cyclopentane vaporized in the kettle was refluxed rapidly and vigorously in order to maintain a large excess of the cyclopentane in contact with the chlorine in the column reaction zone.

The products of chlor-substitution dropped down into the kettle, the temperature of which although maintained above the boiling point of the cyclopentane, was below that of its products of chlorination.

Thus, these products were removed from the reaction zone substantially immediately after their formation.You can easily begin making more cash with just single clicks on your computer.

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