Constitutional isomers alkanes

Among a set of alkane constitutional isomers, the least branched isomer generally has the highest boiling point the most branched isomer generally has the lowest boiling point. 

Methane is the only alkane of molecular formula CH4 ethane the only one that is C2H6 and propane the only one that is C3Hj Beginning with C4H10 however constitutional isomers (Section 1 8) are possible two alkanes have this particular molecular formula In one called n butane, four carbons are joined m a continuous chain The nmn butane stands for normal and means that the carbon chain is unbranched The second isomer has a branched carbon chain and is called isobutane... 

Table 2 3 lists the heats of combustion of several alkanes Unbranched alkanes have slightly higher heats of combustion than their 2 methyl branched isomers but the most important factor is the number of carbons The unbranched alkanes and the 2 methyl branched alkanes constitute two separate homologous senes (see Section 2 9) m which there is a regular increase of about 653 kJ/mol (156 kcal/mol) m the heat of combustion for each additional CH2 group... 

Compounds like the two C4M [() molecules and the three C3I I 12 molecules, which have the same formula but different structures, are called isomers, from the Greek isos + meros, meaning "made of the same parts." Isomers are compounds that have the same numbers and kinds of atoms but differ in the way the atoms are arranged. Compounds like butane and isobutane, whose atoms are connected differently, are called constitutional isomers. We ll see shortly that other kinds of isomers are also possible, even among compounds whose atoms are connected in the same order. As Table 3.2 shows, the number of possible alkane isomers increases dramatically as the number of carbon atoms increases. 

Constitutional isomerism is not limited to alkanes—it occurs widely throughout organic chemistry. Constitutional isomers may have different carbon skeletons (as in isobutane and butane), different functional groups (as in ethanol and dimethyl ether), or different locations of a functional group along the chain (as in isopropylamine and propylamine). Regardless of the reason for the isomerism, constitutional isomers are always different compounds with different properties, but with the same formula. 

Alkanes are a class of saturated hydrocarbons with the general formula C H2n. -2- They contain no functional groups, are relatively inert, and can be either straight-chain (normal) or branched. Alkanes are named by a series of IUPAC rules of nomenclature. Compounds that have the same chemical formula but different structures are called isomers. More specifically, compounds such as butane and isobutane, which differ in their connections between atoms, are called constitutional isomers. 

In the course of doing this problem, you will write and name the 17 alkanes that, in addition to octane, CH3(CH2)6CH3, comprise the 18 constitutional isomers of C8H18. 

They have the same molecular mass, but differ in their manner of linkage, their branching, and in the order (sequence) of their atoms (constitutional isomers). The number of possible isomers increases rapidly in higher generations - by analogy with the classical case of the alkanes. 

Alkanes having a particular molecular formula can exist as different constitutional isomers. For example, the alkane having the molecular formula C4H10can exist as two constitutional isomers-the straight chain alkane (butane) or the branched alkane (2-methylpropane Following fig.). These are different compounds with different physical and chemical properties. 

Constitutional isomers that differ only in the position of a double bond. Double-bond isomers hydrogenate to give the same alkane, (p. 298)... 

Constitutional isomers like butane and isobutane belong to the same family of compounds they are both alkanes. In contrast, constitutional isomers like CH3CH2OH and CH3OCH3 have different functional groups and belong to different families CH3CH2OH is an alcohol and CH3OCH3 is an ether. 

The maximum number of possible constitutional isomers increases dramatically as the number of carbon atoms in the alkane increases, as shown in Table 4.1. For example, there are 75 possible isomers for an alkane having 10 carbon atoms, but 366,319 possible isomers for one having 20 carbons. 

Problem 15.4 Draw all constitutional isomers formed by monochlorination of each alkane. 

We have seen that there are two saturated C Hjq hydrocarbons. For the C5 hydrocarbons, there are three possible arrangements of the atoms. These three different C5H32 alkanes are examples of constitutional isomers. 

The number of constitutional isomers increases rapidly as the number of carbon atoms in saturated hydrocarbons increases. There are live isomeric alkanes (Table 27-3). 

TABLE 27-4 Numbers of Possible Constitutional Isomers of Alkanes... 

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