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In omega-3 fatty acids, the last carbon of the last double bond of the hydrocarbon chain is three carbons from the methyl terminal end of the chain. The last carbon of the chain is called the omega carbon, hence, the designation omega-3. Eicosapentaenoic acid is a common omega-3 fatty acid found in cold water fatty fish and health food supplements. \\[ \mathrm{CH}_{3}\left(\mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}\right)_{5} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{H} \\] Eicosapentaenoic acid a \(\mathrm{C}_{20}\) polyunsaturated fatty acid (a) How many cis-trans isomers are possible for this fatty acid? (b) Draw a line-angle formula for eicosapentaenoic acid, showing the cis configuration of all carboncarbon double bonds in the hydrocarbon chain.

Short Answer

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(a) 32 isomers are possible. (b) Draw the line-angle formula with all cis double bonds.

Step by step solution

01

Define the structure of eicosapentaenoic acid

Eicosapentaenoic acid, often represented as EPA, is a 20-carbon polyunsaturated fatty acid with 5 double bonds. It has the molecular formula \( \text{CH}_3(\text{CH}_2\text{CH}=\text{CH})_5\text{CH}_2\text{CH}_2\text{CH}_2\text{CO}_2\text{H} \). The double bonds are found starting from the 5th carbon in the chain.
02

Determine the possible isomers

Each double bond in the chain can exhibit cis-trans isomerism. Eicosapentaenoic acid with 5 double bonds can theoretically have \( 2^5 = 32 \) possible cis-trans isomers since each double bond can be either in the cis or trans configuration.
03

Draw the line-angle formula

In the line-angle formula, each vertex represents a carbon atom, and lines represent the bonds between them. For eicosapentaenoic acid, the bonds will be drawn such that all five double bonds adopt the cis configuration, forming zig-zag patterns commonly seen in natural fatty acids.

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Key Concepts

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

Eicosapentaenoic Acid
Eicosapentaenoic acid, commonly known as EPA, is one of the essential omega-3 fatty acids crucial for human health. It is primarily found in cold water fish, like mackerel and salmon, and can also be consumed through supplements, such as fish oil capsules. EPA is a polyunsaturated fatty acid, which means it has multiple double bonds within its carbon chain. Specifically, it is composed of 20 carbon atoms and contains five double bonds. These double bonds start from the fifth carbon atom of the chain and are spaced at regular intervals, a structure that gives it specific biochemical properties.

EPA plays a significant role in anti-inflammatory processes and cardiovascular health. It has been linked to reduced risks of heart diseases, making its inclusion in the diet beneficial. Moreover, since the human body cannot synthesize it in sufficient amounts, consuming dietary sources of EPA is essential to meet its physiological needs.
  • Composed of 20 carbon atoms.
  • Contains five double bonds.
  • Primarily sourced from marine life.
Understanding EPA and its function helps illuminate the importance of omega-3 fatty acids in overall health maintenance, emphasizing the need for a balanced diet rich in these beneficial compounds.
Cis-Trans Isomerism
Cis-trans isomerism, sometimes referred to as geometric isomerism, is a form of stereoisomerism. This phenomenon occurs in molecules with double bonds, such as those found in certain fatty acids like eicosapentaenoic acid. When a molecule features a double bond, the atoms attached to the bonded carbons can arrange themselves in different orientations, leading to distinct isomers.

In the cis configuration, both atoms or groups of interest are on the same side of the double bond, causing a bend in the molecule. Meanwhile, in the trans configuration, these groups are on opposite sides, resulting in a more linear structure. For eicosapentaenoic acid, which contains five double bonds, theoretically, each bond can switch between these configurations, leading to potential isomers of the molecule.
  • Cis: Atoms/groups on the same side.
  • Trans: Atoms/groups on opposite sides.
  • Can result in multiple isomers due to different possible configurations.
The biological activity of fatty acids can be significantly influenced by their isomerism. Typically, in natural fatty acids like EPA, the cis configuration is more common as it confers a specific shape and biologic activity critical for their role in health. Understanding these configurations can help explain why certain fats are found in specific structural forms within food sources.
Polyunsaturated Fatty Acids
Polyunsaturated fatty acids (PUFAs) are a type of essential fat found predominantly in plants and marine organisms. They are characterized by having two or more double bonds within their carbon chains. These fats play crucial roles in the body, including hormone production, inflammatory process regulation, and maintaining cell membrane integrity.

Why are PUFAs important? First, the presence of multiple double bonds introduces bends and twists in the carbon chain, which prevent the molecules from packing tightly. This quality helps to maintain the fluidity of cell membranes, which is vital for cell function and communication. In addition, PUFAs like omega-3 and omega-6 fatty acids are precursors to signaling molecules that help regulate inflammation and other critical physiological processes.
  • Contains two or more double bonds.
  • Essential for maintaining cell membrane fluidity.
  • Involved in inflammatory processes and hormonal balance.
Among the various types of PUFAs, those classified as omega-3, including linolenic acid, EPA, and DHA, are particularly beneficial for cardiovascular health. They help decrease triglyceride levels and may lower the risk of heart arrhythmias. By understanding the structure, importance, and dietary sources of polyunsaturated fatty acids, individuals can better appreciate how these compounds contribute to a healthy lifestyle.

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Most popular questions from this chapter

Acid-catalyzed hydration of 2-pentene gives a mixture of two alcohols, each with the molecular formula \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O} .\) Draw the structural formula for both alcohols. Similar treatment of 3 -hexene gives only one alcohol with the molecular formula \(\mathrm{C}_{6} \mathrm{H}_{14} \mathrm{O}\). Draw the structural formula for this alcohol.

Answer true or false. (a) Alkenes, alkynes, and arenes are unsaturated hydrocarbons. (b) Aromatic compounds were so named because many of them have pleasant odors. (c) According to the resonance model of bonding, benzene is best described as a hybrid of two equivalent contributing structures. (d) Benzene is a planar molecule.

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.

cis-3-Hexene and trans-3-hexene are different compounds and have different physical and chemical properties. Yet, when treated with \(\mathrm{H}_{2} \mathrm{O} / \mathrm{H}_{2} \mathrm{SO}_{4},\) each gives the same alcohol. What is this alcohol, and how do you account for the fact that each alkene gives the same one?

Both phenol and cyclohexanol are only slightly soluble in water. Account for the fact that phenol dissolves in aqueous sodium hydroxide but cyclohexanol does not.

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