Straight-chained alkanes

Paraffins consist mainly of straight chain alkanes, with a very small proportion of isoalkanes and cycloalkanes. Their freezing point is generally between 30°C and 70°C, the average molecular weight being around 350. When present, aromatics appear only in trace quantities. 

Isomerization (rearrangement) of hydrocarbons is of substantial practical importance. Straight-chain alkanes obtained from petroleum... 

Unbranched alkanes are sometimes referred to as straight chain alkanes but as we 11 see m Chapter 3 their chains are not straight but instead tend to adopt the zigzag shape portrayed m the bond line formulas introduced m Section 1 7... 

Mote stable catalysts ate obtained by using fluorinated graphite or fluorinated alumina as backbones, and Lewis acid halides, such as SbF, TaF, and NbF, which have a relatively low vapor pressure. These Lewis acids ate attached to the fluorinated soHd supports through fluorine bridging. They show high reactivity in Friedel-Crafts type reactions including the isomerization of straight-chain alkanes such as / -hexane. 

If the heat of fonnation parameters are derived on the basis of fitting to a large variety of compounds, a specific set of parameters is obtained. A slightly different set of parameters may be obtained if only certain strainless molecules are included in the parameterization. Typically molecules like straight chain alkanes and cyclohexane are defined as strainless. Using these strainless heat of formation parameters, a strain energy may be calculated as illustrated in Figure 2.14. 

Isomers are substances having the same molecular formula and molecular weight, but differing in physical and chemical properties. Since branched and straight-chain alkanes with the same molecular formula can exist as distinct structures having different geometrical arrangement of the atoms, they are termed structural isomers. One example is C H,j (butane) which has two isomers ... 

Compounds like butane and pentane, whose carbons are all connected in a row, are called straight-chain alkanes, or normal alkanes. Compounds like 2-methylpropane (isobutane), 2-methylbutane, and 2,2-dimethylpropane, whose carbon chains branch, are called branched-chain alkanes. The difference between the two is that you can draw a line connecting all the carbons of a straight-chain alkane without retracing your path or lifting your pencil from... 

Straight-chain alkanes are named according to the number of carbon atoms they contain, as shown in Table 3.3. With the exception of the first four compounds—methane, ethane, propane, and butane—whose names have historical roots, the alkanes are named based on Greek numbers. The suffix -one is added to the end of each name to indicate that the molecule identified is an alkane. Thus, pentane is the five-carbon alkane, hexeme is the six-carbon alkane, and so on. We ll soon see that these alkane names form the basis for naming all other organic compounds, so at least the first ten should be memorized. 

Figure 3.3 Alkyl groups generated from straight-chain alkanes.

Another interesting effect seen in alkanes is that increased branching lowers an alkane s boiling point. Thus, pentane has no branches and boils at 36.1 3C, isopentane (2-methylbutane) has one branch and boils at 27.85 °C, and neopentane (2,2-dimethylpropane) has two branches and boils at 9.5 °C. Similarly, octane boils at 125.7 °C, whereas isooctane (2,2,4-trimethylpentane) boils at 99.3 °C. Branched-chain alkanes are lower-boiling because they are more nearly spherical than straight-chain alkanes, have smaller surface areas, and consequently have smaller dispersion forces. 

Branched-chain alkane (Section 3.2) An alkane that contains a branching connection of carbons as opposed to a straight-chain alkane. 

Straight-chain alkane, 80 Strecker synthesis, 972 Structure, condensed, 22 electron-dot, 9 Kekule, 9 Lewis, 9 line-bond, 9 skeletal, 23... 

The names of straight-chain alkanes are given in Table 18.1 they all end in -ane. Name a hydrocarbon side chain as a substituent by changing the ending -ane to -yl (as in the last two columns in Table 18.1). 

FIGURE 18.5 (a) The atoms in neighboring straight-chain alkanes, represented by the tubelike structures, can lie close together. Ibl Fewer of the atoms of neighboring branched alkane molecules can get so close together overall, and so the London forces (represented by double-headed arrows) are weaker and branched alkanes are more volatile. 

These effects are very much smaller than those found for the first-order solvolyses of bornyl and isobornyl chlorides, which differ in relative rate by several orders of magnitude. However, the authors argue that this does not necessarily disprove participation by a carbonium ion in the mechanism which they proposed for the oxidation of straight-chain alkanes (see above). 

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