NOVEL THINKING

What are the similarities? 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? If the position of the alkene is unambiguous, the locant is not required, Functional group is an alkene, therefore suffix = -, The longest continuous chain is C3 therefore root =, In order to give the alkene the lowest number, number from the, The longest continuous chain is C4 therefore root =, The C=C is between C2 and C3 so the locant is, The C=C is between C1 and C2 so the locant is, The longest continuous chain is C6 therefore root =, The longest continuous chain is C5 therefore root =, The C=C is between C3 and C4 so the locant is, The first point of difference rule requires numbering from the. If you examine the structural formulas for the following cycloalkenes, you will see that the configuration of the double bond is cis in each.All attempts to synthesize these cycloalkenes in which the double bond has a trans configuration have failed. What do these two structural features have in common? What is the difference in structure between a saturated and an unsaturated hydrocarbon? Draw structural formulas for all possible carbocations formed by the reaction of each alkene with HCl. Name and draw a structural formula for each product.

Name the type of reaction that occurs in each step and suggest a reason why the sequence is called $\beta$ -oxidation. Draw a structural formula for $\beta$ -ocimene. Draw a structural formula for an alkene with the molecular formula $\mathrm{C}_{5} \mathrm{H}_{10}$ that reacts with $\mathrm{HCl}$ to give the indicated chloroalkane as the major product. 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. When toluene is treated with $\mathrm{Br}_{2}$ in the presence of an $\mathrm{AlBr}_{3}$ catalyst, a mixture of three compounds is formed, all with the molecular formula $\mathrm{C}_{7} \mathrm{H}_{7}$ Br. Answer true or false. As you draw these alkenes, remember that cis and trans isomers are different compounds and must be counted separately. (a) Ethylene contains one carbon-carbon double bond, and polyethylene contains many carboncarbon double bonds. There are different isomers which can be drawn for C 4 H 8 O molecular formula. (a) A phenyl group has the molecular formula $\mathrm{C}_{6} \mathrm{H}_{5}-$ and is represented by the symbol $\mathrm{Ph}-$(b) Para substituents occupy adjacent carbons on a benzene ring. (a) $\mathrm{V}$(b) $\mathrm{PP}$(c) PS. Draw the structural formula of an alkene that undergoes acid-catalyzed hydration to give the indicated alcohol as the major product. How many cis/trans isomers are possible for each?$$\begin{array}{c}\text { Oleic acid } \mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{7} \mathrm{CH}=\mathrm{CH}\left(\mathrm{CH}_{2}\right)_{7} \mathrm{COOH} \\\text { Linoleic acid } \mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{4}\left(\mathrm{CH}=\mathrm{CHCH}_{2}\right)_{2}\left(\mathrm{CH}_{2}\right)_{6} \mathrm{COOH} \\\text { Linolenic acid } \mathrm{CH}_{3} \mathrm{CH}_{2}\left(\mathrm{CH}=\mathrm{CHCH}_{2}\right)_{3}\left(\mathrm{CH}_{2}\right)_{6} \mathrm{COOH}\end{array}$$. Explain.

(b) An alkene in which each carbon of the double bond has two different groups bonded to it will show cis-trans isomerism. (b) Draw a structural formula for the product formed when albuterol is treated with one equivalent of aqueous sodium hydroxide. (n) Acid-catalyzed hydration of 1-butene gives 1-butanol. In plants, this compound is almost always present in combination with chlorophyll to assist in the harvesting of the energy of sunlight. What reagent and/or catalysts are necessary to bring about each conversion? Each nitrogencontaining compound shows the characteristic reactions of benzene and its derivatives each is highly unsaturated but does not undergo the characteristic addition reactions of alkenes. Label each carbocation as primary, secondary, or tertiary. It can only be used to prepare secondary and tertiary alcohols from alkenes in good yield. Draw a structural formula for the product formed by treatment of 2 -methyl-2-pentene with each reagent. One analogy often used to explain the concept of a resonance hybrid is to relate a rhinoceros to a unicorn and a dragon. (Chemical Connections $12 \mathrm{E}$ ) In what ways is capsaicin used in medicine? (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. (Chemical Connections $12 \mathrm{E}$ ) From what types of plants is capsaicin isolated? Answer true or false.

What are the differences? (a) Benzene to nitrobenzene(b) 1,4 -Dichlorobenzene to 2 -bromo-1,4-dichlorobenzene(c) Benzene to aniline. (a) $t r a n s-2$ -Methyl-3-hexene(b) $2-$ Methyl-3-hexyne(c) $2-$ Methyl-1-butene(d) 3 -Ethyl-3-methyl-1-pentyne(e) 2,3 -Dimethyl-2-pentene, Draw a structural formula for each compound. (b) The bulk of the ethylene used by the chemical industry worldwide is obtained from renewable resources.

(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. We have lot of functional groups in organic chemistry such as acids, acid derivatives, aldehydes, ketones, alcohols, amines and so many other groups. Explain why goiter is a regional disease.

Name and draw structural formulas for all alkenes with the molecular formula $\mathrm{C}_{5} \mathrm{H}_{10}$. (a) There are two classes of unsaturated hydrocarbons-alkenes and alkynes. Functional group priority list. (j) Addition of $\mathrm{H}_{2}$ to a double bond is a reduction reaction.

(d) Benzene is a planar molecule. (Cis refers to the configuration of the double bond between carbons 3 and $4,$ the only double bond in this molecule about which cis -trans isomerism is possible. (a) $1-$ Hexene gives one alcohol with a molecular formula of $\mathrm{C}_{6} \mathrm{H}_{14} \mathrm{O}$(b) 2 -Hexene gives two alcohols, each with a molecular formula of $\mathrm{C}_{6} \mathrm{H}_{14} \mathrm{O}$(c) 3 -Hexene gives one alcohol with a molecular formula of $\mathrm{C}_{6} \mathrm{H}_{14} \mathrm{O}$. Therefore, alkenes are unsaturated hydrocarbons. Propose a structural formula for the product(s) when each of the following alkenes is treated with $\mathrm{H}_{2} \mathrm{O} / \mathrm{H}_{2} \mathrm{SO}_{4} .$ Why are two products formed in part(b), but only one in parts (a) and (c)?

More than one alkene may give each compound as the major product. Acid-catalyzed hydration of $c i s$ - or trans-3-hexene gives a single alcohol in high yield. Show how to convert cyclopentene into these compounds. Predict all bond angles about each highlighted carbon atom. What is the difference in structure between a saturated hydrocarbon and an unsaturated hydrocarbon? (c) Predict the bond angles in pyridine and pyrimidine and the shape of each molecule. (Chemical Connections $12 \mathrm{C}$ ) Would you expect DDT to be soluble or insoluble in water? (a) $1-$ Pentene(b) $2-$ Pentene(c) 3 -Ethyl-2-pentene(d) 2,3 -Dimethyl-2-pentene(e) 2 -Methyl-2-pentene(f) 2,4 -Dimethyl-2-pentene. (a) Propose a structural formula for terpin.

Hence “methene” doesn’t exist. (d) Cyclohexane and 1-hexene are constitutional isomers. (For more information about alkyl groups, see Chapter 1 "Organic Chemistry Review / Hydrocarbons", Section 1.5 "IUPAC Nomenclature". (a) Name the functional groups present in albuterol. Write line-angle formulas for all compounds with the molecular formula $\mathrm{C}_{4} \mathrm{H}_{8}$. (Chemical Connections $12 \mathrm{C}$ ) What are the advantages and disadvantages of using DDT as an insecticide? Arachidonic acid is a naturally occurring $\mathrm{C}_{20}$ poly unsaturated fatty acid. (a) 1,2 -Dibromocyclopentane(b) Cyclopentanol(c) Iodocyclopentane(d) Cyclopentane.

(c) According to the resonance model of bonding, benzene is best described as a hybrid of two equivalent contributing structures. Then identify the error, for example, failure to locate the longest chain that contains the alkene functional group, etc., and then write the correct name. (b) Show that each aromatic compound has an aromatic sextet-that is, a loop of six electrons within a cyclic system. Name and draw structural formulas for alkenes with the molecular formula $\mathrm{C}_{6} \mathrm{H}_{12}$ that have the following carbon skeletons (remember cis and trans isomers). Answer true or false. General Formula: CnH2n, n = 2, 3, 4, ….Functional Group:Double BondFirst 3 Members:Chemical Properties:MUST Know!Alkenes are unsaturated hydrocarbons.Alkenes are a family of hydrocarbons (compounds containing carbon and hydrogen only) containing a carbon-carbon double bond.

Write the IUPAC name for each unsaturated hydrocarbon. In addition, it persists in the environment.

Explain what you would do, what you would expect to see, and how you would explain your observations. More than one alkene may give the same compound as the major product. (a) 2 -Ethyl-1-propene(b) 5 -Isopropylcyclohexene(c) $4-$ Methyl- 4 -hexene(d) $2-\sec$ -Butyl-1-butene(e) 6,6 -Dimethylcyclohexene(f) 2-Ethyl-2-hexene. 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. (a) Ethane(b) Ethanol(c) Bromoethane(d) 1,2 -Dibromoethane(e) Chloroethane, Show how to convert 1-butene to these compounds. Therefore, alkenes are unsaturated hydrocarbons.The general formula for alkene is CnH2n where n = 2, 3, …

Following is the structural formula of albuterol (Proventil), one of the most widely used inhalation bronchodilators. This compound was at one time used as a flame retardant in polystyrene foam insulation in buildings, but has now been banned because it had been shown to be toxic to aquatic organisms, and can disrupt thyroid hormone levels in laboratory test animals. Explain the reasoning in this analogy and how it might relate to a resonance hybrid.

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