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What structural feature in alkenes makes cis-trans isomerism in them possible? What structural feature in cycloalkanes makes cis-trans isomerism in them possible? What do these two structural features have in common?

Short Answer

Expert verified
Cis-trans isomerism in alkenes is due to the double bond; in cycloalkanes, it is due to the ring structure. Both restrict rotation.

Step by step solution

01

Understand Cis-Trans Isomerism in Alkenes

To understand cis-trans isomerism in alkenes, we must first consider the basic structure of an alkene, which includes a carbon-carbon double bond. This double bond restricts rotation, creating two distinct spatial arrangements for groups attached to these carbons. If two identical groups are attached to the carbons of the double bond on the same side, it is a 'cis' isomer. If they are on opposite sides, it is a 'trans' isomer.
02

Understand Cis-Trans Isomerism in Cycloalkanes

Cycloalkanes can also exhibit cis-trans isomerism due to their ring structure, which restricts the rotation of carbon atoms within the ring. In cycloalkanes, if two substituents are on the same side of the ring, it is a 'cis' isomer; if they are on opposite sides, it is a 'trans' isomer. Unlike alkenes, this restriction is due to the cyclical nature of the compound rather than a double bond.
03

Compare Structural Features of Alkenes and Cycloalkanes

Both alkenes and cycloalkanes exhibit restricted rotation, although for different reasons. Alkenes have restricted rotation because of the electron cloud formed by the double bond, while cycloalkanes have restricted rotation due to the rigidity of their ring structure. Both features ultimately prevent free rotation and allow for different spatial arrangements of atoms, leading to cis-trans isomerism.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Alkenes
Alkenes are hydrocarbons that contain at least one carbon-carbon double bond in their structure. This double bond is crucial because it significantly alters the properties of the molecule, making alkenes distinct from their alkane counterparts, which only have single bonds. The double bond is responsible for many of the characteristic reactions that alkenes undergo. Moreover, this double bond is vital for a particular type of isomerism known as cis-trans isomerism (or geometric isomerism).

One of the defining features of this bond is the planar arrangement of the atoms involved. This means that the component atoms, particularly the carbons involved in the double bond and their directly attached groups, lie in the same plane. This arrangement leads to the creation of potential isomers, depending on the spatial orientation of these groups. Thus, the structural attribute of the double bond itself is essential for alkenes to exhibit cis-trans isomerism.
Cycloalkanes
Cycloalkanes are saturated hydrocarbons that have a ring structure. Unlike alkenes, cycloalkanes do not possess double bonds but still can show cis-trans isomerism due to the rigid structure of the ring itself. The ring restricts the rotation of atoms bonded to it, which allows for the possibility of having different spatial arrangements of substituents around the ring.

In cycloalkanes, cis-trans isomerism is determined by the relative positions of substituents attached to the ring. Two substituents on the same side of the cycloalkane form a 'cis' isomer, while those on opposite sides form a 'trans' isomer. The ring’s rigidity, therefore, plays a role similar to that of the double bond in alkenes, in that it prevents free rotation and allows isomerism to occur.
Double Bond
The double bond is a key structural feature in alkenes that allows for restricted rotation, leading to the possibility of cis-trans isomerism. It consists of one sigma bond and one pi bond. The pi bond results from the side-to-side overlap of p orbitals. This pi bond creates an electron cloud above and below the plane of the atoms involved in the double bond.

The electron density in the pi bond prevents the atoms involved in the double bond from rotating freely, unlike in single bonds, where such rotation is possible. This restriction means groups attached to these carbon atoms have fixed spatial relationships, enabling the existence of distinct isomers such as 'cis' and 'trans'. Such isomers are distinguishable by the position of their constituent groups in space relative to the double bond.
Restricted Rotation
Restricted rotation is a fundamental concept that allows both alkenes and cycloalkanes to exhibit cis-trans isomerism. In alkenes, this restriction is due to the presence of a carbon-carbon double bond, where the pi bond portion impedes rotation. The electrons in the pi bond form a cloud that locks the arrangement in place.

In cycloalkanes, restricted rotation stems from the cyclic structure. The atoms within the ring are bound in such a way that they cannot freely rotate around the bonds that connect them in the same manner as linear alkanes. This restriction means the spatial configuration of substituents around the ring is fixed, similar to the effects of a double bond in alkenes. As a result, both alkenes and cycloalkanes can form different isomers based on the arrangements of atoms, manifesting in the characteristic cis-trans isomerism.

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Most popular questions from this chapter

Answer true or false. (a) Both ethylene and acetylene are planar molecules. (b) An alkene in which each carbon of the double bond has two different groups bonded to it will show cis-trans isomerism. (c) Cis -trans isomers have the same molecular formula but a different connectivity of their atoms. (d) \(C i s-2\) -butene and \(t r a n s-2\) -butene can be interconverted by rotation about the carbon-carbon double bond. (e) Cis -trans isomerism is possible only among appropriately substituted alkenes. (f) Both 2-hexene and 3-hexene can exist as pairs of cis-trans isomers. (g) Cyclohexene can exist as a pair of cis-trans isomers. (h) \(1-\) Chloropropene can exist as a pair of cis -trans isomers.

Three products with the molecular formula \(\mathrm{C}_{6} \mathrm{H}_{4} \mathrm{BrCl}\) form when bromobenzene is treated with chlorine, \(\mathrm{Cl}_{2}\) in the presence of \(\mathrm{FeCl}_{3}\) as a catalyst. Name and draw a structural formula for each product.

Answer true or false. (a) Complete combustion of an alkene gives carbon dioxide and water. (b) Addition reactions of alkenes involve breaking one of the bonds of the carbon-carbon double bond and formation of two new single bonds in its place. (c) Markovnikov's rule refers to the regioselectivity of addition reactions of carbon-carbon double bonds. (d) According to Markovnikov's rule, in the addition of \(\mathrm{HCl}\), \(\mathrm{HBr}\), or \(\mathrm{HI}\) to an alkene, hydrogen adds to the carbon of the double bond that already has the greater number of hydrogen atoms bonded to it and the halogen adds to the carbon that has the lesser number of hydrogens bonded to it. (e) A carbocation is a carbon atom with four bonds that bears a positive charge. (f) The carbocation derived from ethylene is \(\mathrm{CH}_{3} \mathrm{CH}_{2}^{+}\) (g) The reaction mechanism for the addition of a halogen acid (HX) to an alkene is divided into two steps, (1) formation of a carbocation and (2) reaction of the carbocation with halide ion, which complete the reaction. (h) Acid-catalyzed addition of \(\mathrm{H}_{2} \mathrm{O}\) to an alkene is called hydration. (i) If a compound fails to react with \(\mathrm{Br}_{2}\), it is unlikely that the compound contains a carbon-carbon double bond. (j) Addition of \(\mathrm{H}_{2}\) to a double bond is a reduction reaction. (k) Catalytic reduction of cyclohexene gives hexane. (l) According to the mechanism presented in the text for acid-catalyzed hydration of an alkene, the H and \(-\) OH groups added to the carbon-carbon double bond both arise from the same molecule of \(\mathrm{H}_{2} \mathrm{O}\) \((\mathrm{m})\) The conversion of ethylene, \(\mathrm{CH}_{2}=\mathrm{CH}_{2},\) to ethanol \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH},\) is an oxidation reaction. (n) Acid-catalyzed hydration of 1-butene gives 1-butanol. Acid-catalyzed hydration of 2-butene gives 2 -butanol.

Arachidonic acid is a naturally occurring \(\mathrm{C}_{20}\) poly unsaturated fatty acid. Draw a line-angle formula for arachidonic acid showing the cis configuration about each double bond. \\[ \mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{4}\left(\mathrm{CH}=\mathrm{CHCH}_{2}\right)_{4} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{COOH} \\]

Answer true or false. (a) Alkenes and alkynes are nonpolar molecules. (b) The physical properties of alkenes are similar to those of alkanes of the same carbon skeletons. (c) Alkenes that are liquid at room temperature are insoluble in water and when added to water, will float on water.

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