Draw structural formulas for all possible carbocations formed by the reaction of each alkene with HCl. (a) Ethylene contains one carbon-carbon double bond, and polyethylene contains many carboncarbon double bonds.
Draw the structural formula for a cycloalkene with the molecular formula $\mathrm{C}_{6} \mathrm{H}_{10}$ that reacts with $\mathrm{Cl}_{2}$ to give each compound. Draw at least two structural formulas for each of the following. (c) Ethylene and acetylene are constitutional isomers. Answer true or false. Draw a line-angle formula of each acid, showing clearly the configuration of the carbon-carbon double bond in each.
Which are sets of constitutional isomers?
The fatty acids in Problem 94 occur in animal fats, vegetable oils, and biological membranes almost exclusively as the all-cis isomers. (b) A defining feature of aromatic compounds is that they are highly unsaturated but do not undergo characteristic alkene addition reactions. In plants, this compound is almost always present in combination with chlorophyll to assist in the harvesting of the energy of sunlight.
As you draw these alkenes, remember that cis and trans isomers are different compounds and must be counted separately. (c) The $\mathrm{p} K_{\mathrm{a}}$ of phenol is smaller than that of acetic acid.
For each that does, draw structural formulas for both isomers.
(Chemical Connections 12E) How many cis-trans isomers are possible for capsaicin? (Chemical Connections $12 \mathrm{E}$ ) Identify the phenol group in capsaicin. What are the differences? $\beta$ -Ocimene, a triene found in the fragrance of cotton blossoms and several essential oils, has the IUPAC name $c i s-3,7$ -dimethyl-1,3,6-octatriene. Answer true or false. (c) 4 -Bromobenzoic acid can be separated into cis and trans isomers. (Chemical Connections $12 \mathrm{C}$ ) One of the degradation products of DDT is dichlorodiphenyldichloroethylene (DDE), which is formed by the loss of HCl from adjacent carbons of DDT. For each molecule that shows cis-trans isomerism, draw the cis isomer.
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. 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. What reagents and/or catalysts are necessary to carry out each conversion?
C 4 H 8 O Isomers | Chain, Functional, Cyclic Isomers of C 4 H 8 O. What types of products are made of low-density polyethylene?
Write line-angle formulas for all compounds with the molecular formula $\mathrm{C}_{4} \mathrm{H}_{8}$.
(a) Benzene does not undergo the addition reactions that are characteristic of alkenes.
Benzene, as we have seen in this chapter, is the simplest aromatic compound. A group which act as principle functional group in one structure may be treated as side chain in other instances. )(a) An alkene with six carbons(b) A cycloalkene with six carbons(c) An alkyne with six carbons(d) An aromatic hydrocarbon with eight carbons. (e) A carbocation is a carbon atom with four bonds that bears a positive charge. Explain how the VSEPR model (Section 3.10 ) predicts a bond angle of $109.5^{\circ}$ about each carbon in ethane but an angle of $120^{\circ}$ about each carbon in ethylene. Functional group priority list. (d) Benzene is a planar molecule. (a) $1-$ Bromo- 2 -chloro- 4 -ethylbenzene(b) $4-$ Bromo- 1,2 -dimethylbenzene(c) $2,4,6-$ Trinitrotoluene(d) 4 -Phenyl-1-pentene(e) $p$ -Cresol(f) 2,4 -Dichlorophenol. Fatty acids are metabolized by this pathway to produce energy. Draw structural formulas for these compounds. Answer true or false. We use the same code for the stem, as the alkane.
Which is which? (e) Cis -trans isomerism is possible only among appropriately substituted alkenes. (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}$$(\mathrm{m})$ The conversion of ethylene, $\mathrm{CH}_{2}=\mathrm{CH}_{2},$ to ethanol $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH},$ is an oxidation reaction. In omega-3 fatty acids, the last carbon of the last double bond of the hydrocarbon chain is three carbons from the methyl terminal end of the chain. With the notable exception of ethanol, the acidcatalyzed hydration of alkenes cannot be used to prepare primary alcohols. (a) There are two classes of unsaturated hydrocarbons-alkenes and alkynes.
(j) Addition of $\mathrm{H}_{2}$ to a double bond is a reduction reaction. (a) Propose a structural formula for terpin. (a) $\mathrm{CH}_{2}=\mathrm{CH}\left(\mathrm{CH}_{2}\right)_{4} \mathrm{CH}_{3}$b) c)(d) $\quad\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCH}=\mathrm{C}\left(\mathrm{CH}_{3}\right)_{2}$(e) $\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{5} \mathrm{C} \equiv \mathrm{CH}$$(\mathrm{f}) \quad \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C}=\mathrm{CC}\left(\mathrm{CH}_{3}\right)_{3}$g). Name and draw structural formulas for all compounds with the molecular formula $\mathrm{C}_{5} \mathrm{H}_{10}$ that are:(a) Alkenes that do not show cis-trans isomerism(b) Alkenes that show cis-trans isomerism(c) Cycloalkanes that do not show cis-trans isomerism(d) Cycloalkanes that show cis-trans isomerism. (c) Draw a structural formula for the product formed when albuterol is treated with one equivalent of hydrochloric acid. (For more information about alkyl groups, see Chapter 1 "Organic Chemistry Review / Hydrocarbons", Section 1.5 "IUPAC Nomenclature".
As alkane, the name of straight-chain alkenes is also made up of two component parts, the stem and the suffix.
Show how this flame retardant could be synthesized from a cycloalkatriene and write the structural formula and IUPAC name of this starting material. (f) PS and PVC are currently recycled. (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. Therefore, alkenes are unsaturated hydrocarbons. 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).
(a) The IUPAC name of an alkene is derived from the name of the longest carbon chain that contains the carbon-carbon double bond. (a) $1-$ Methylpropene(b) $3-$ Pentene(c) $2-$ Methylcyclohexene(d) 3,3 -Dimethylpentene(e) $4-$ Hexyne(f) 2-Isopropyl-2-butene, Explain why each name is incorrect and then write a correct name.
What do these two structural features have in common?
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) Draw a line-angle formula for eicosapentaenoic acid, showing the cis configuration of all carboncarbon double bonds in the hydrocarbon chain. How many of the carbon-carbon double bonds in lycopene have the possibility for cis-trans isomerism? Draw a structural formula for at least one bromoalkene with the molecular formula $\mathrm{C}_{5} \mathrm{H}_{9} \mathrm{Br}$ that(a) shows cis$/$trans isomerism and(b) does not show cis/trans isomerism.
Five of these were given in Problem $44 .$ Draw structural formulas for the other four, and predict the product(s) of the acid-catalyzed hydration of each. 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.
For example, Similar treatment of 3 -hexene gives only one alcohol with the molecular formula $\mathrm{C}_{6} \mathrm{H}_{14} \mathrm{O}$.
Account for the fact that the six-membered ring in benzene is planar but the six-membered ring in cyclohexane is not.
(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.
Following is the structural formula of albuterol (Proventil), one of the most widely used inhalation bronchodilators.
Explain why each name is incorrect and then write a correct name. Show how to convert ethylene to these compounds. (b) All $\mathrm{C}-\mathrm{C}-\mathrm{C}$ bond angles in both LDPE and HDPE are approximately $120^{\circ}$(c) Low-density polyethylene (LDPE) is a highly branched polymer. (Chemical Connections 12 A) In which isomer of retinal is the end-to-end distance longer, the all-trans isomer or the 11 -cis isomer? One type of polyethylene is currently recyclable, and the other is not.
(Several constitutional isomers are possible for each part. 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. Answer true or false.
In addition, it persists in the environment. (i) If a compound fails to react with $\mathrm{Br}_{2}$, it is unlikely that the compound contains a carbon-carbon double bond.
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