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Chapter 5: Problem 13

Draw structural formulas for these alkenes. (a) trans-2-Methyl-3-hexene (b) 2-Methyl-2-hexene (c) 2-Methyl-1-butene (d) S-Ethyl-3-methyl-1-pentene (e) 2,3-Dimethyl-2-butene (f) cis-2-Pentene (g) (Z)-1-Chloropropene (h) S-Methylcyclohexene (i) 1-Isopropyl-4-methylcyclohexene (j) (E)-2,6-Dimethyl-2,6-octadiene (k) 3-Cyclopropyl-1-propene (1) Cyclopropylethene (m) 2-Chloropropene (n) Tetrachloroethylene (o) 1-Chlorocyclohexene

Short Answer

Expert verified
Question: Draw the structural formulas for the following alkenes: (a) trans-2-Methyl-3-hexene (b) 2-Methyl-2-hexene (c) 2-Methyl-1-butene (d) S-Ethyl-3-methyl-1-pentene (e) 2,3-Dimethyl-2-butene (f) cis-2-Pentene (g) (Z)-1-Chloropropene (h) S-Methylcyclohexene (i) 1-Isopropyl-4-methylcyclohexene (j) (E)-2,6-Dimethyl-2,6-octadiene (k) 3-Cyclopropyl-1-propene (l) Cyclopropylethene (m) 2-Chloropropene (n) Tetrachloroethylene (o) 1-Chlorocyclohexene

Step by step solution

01

(a) trans-2-Methyl-3-hexene

Begin by drawing a hexene molecule, which is a six-carbon alkene with the double bond between the second and third carbon. Then, add a methyl group to the second carbon atom, making sure to place it on the opposite side of the double bond as the rest of the chain to ensure it is a trans configuration.
02

(b) 2-Methyl-2-hexene

Draw a hexene molecule with the double bond between the first and second carbon atoms. Add a methyl group to the second carbon atom.
03

(c) 2-Methyl-1-butene

Draw a butene molecule with the double bond between the first and second carbon atoms. Add a methyl group to the second carbon atom.
04

(d) S-Ethyl-3-methyl-1-pentene

Draw a pentene molecule with the double bond between the first and second carbon atoms, and with the ethyl and methyl groups attached to their respective positions. S refers to the absolute steric configuration, which we can omit for simplicity.
05

(e) 2,3-Dimethyl-2-butene

Draw a butene molecule with the double bond between the first and second carbon atoms. Then, add methyl groups to the second and third carbon atoms.
06

(f) cis-2-Pentene

Draw a pentene molecule with the double bond between the second and third carbon atoms. Ensure that the longer parts of the chain are on the same side of the double bond, indicating a cis configuration.
07

(g) (Z)-1-Chloropropene

Draw a propene molecule with the double bond between the first and second carbon atoms. Attach a chlorine atom to the first carbon atom, making sure that the two larger groups are on the same side of the double bond, indicating a (Z) configuration.
08

(h) S-Methylcyclohexene

Draw a cyclohexene molecule, which is a hexagon with one double bond. Attach a methyl group to a carbon atom adjacent to the double bond. Again, S refers to the absolute steric configuration, but we can omit it for simplicity.
09

(i) 1-Isopropyl-4-methylcyclohexene

Draw a cyclohexene molecule and attach an isopropyl group (two carbon atoms branching off) to the first carbon atom and a methyl group to the fourth carbon atom.
10

(j) (E)-2,6-Dimethyl-2,6-octadiene

Draw an octadiene molecule with double bonds between the second and third carbon atoms and between the sixth and seventh carbon atoms. Attach methyl groups to the second and sixth carbon atoms, ensuring that the larger groups around the double bonds are on opposite sides, indicating an (E) configuration.
11

(k) 3-Cyclopropyl-1-propene

Draw a propene molecule with the double bond between the first and second carbon atoms. Attach a cyclopropyl group (a three-carbon ring) to the third carbon atom.
12

(l) Cyclopropylethene

Draw an ethene molecule (two carbon atoms connected by a double bond) and attach a cyclopropyl group to one of the carbon atoms.
13

(m) 2-Chloropropene

Draw a propene molecule with the double bond between the first and second carbon atoms and attach a chlorine atom to the second carbon atom.
14

(n) Tetrachloroethylene

Draw an ethene molecule and attach a chlorine atom to each of the carbon atoms.
15

(o) 1-Chlorocyclohexene

Draw a cyclohexene molecule and attach a chlorine atom to the first carbon atom.

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Most popular questions from this chapter

Which alkenes exist as pairs of cis, trans isomers? For each that does, draw the trans isomer. (a) \(\mathrm{CH}_{2}=\mathrm{CHBr}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHBr}\) (c) \(\mathrm{BrCH}=\mathrm{CHBr}\) (d) \(\left(\mathrm{CH}_{\mathrm{s}}\right)_{2} \mathrm{C}=\mathrm{CHCH}_{3}\) (e) \(\left(\mathrm{CH}_{5}\right)_{2} \mathrm{CHCH}=\mathrm{CHCH}_{3}\)

Trans-cyclooctene has been resolved, and its enantiomers are stable at room temperature. Trans-cyclononene has also been resolved, but it racemizes with a half-life of \(4 \mathrm{~min}\) at \(0^{\circ} \mathrm{C}\). How can racemization of this cycloalkene take place without breaking any bonds? Why does trans- cyclononene racemize under these conditions but trans-cyclooctene does not? You will find it especially helpful to examine the molecular models of these cycloalkenes.

Bromine adds to cis and trans-2-butene to give different diastereomers of 2,3 -dibromobutane. What does this say about the mode of addition of bromine to this alkene?

Four stereoisomers exist for S-penten-2-ol. (a) Explain how these four stereoisomers arise. (b) Draw the stereoisomer having the \(E\) configuration about the carbon-carbon double bond and the \(R\) configuration at the chiral center.

Draw the structural formula for at least one bromoalkene with the molecular formula \(\mathrm{C}_{5} \mathrm{H}_{9} \mathrm{Br}\) that shows: (a) Neither \(E, Z\) isomerism nor chirality. (b) \(E, Z\) isomerism but not chirality. (c) Chirality but not \(E, Z\) isomerism. (d) Both chirality and \(E, Z\) isomerism.
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