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Chapter 9: Problem 6

Predict the \(\beta\)-elimination product(s) formed when each chloroalkane is treated with sodium ethoxide in ethanol. If two or more products might be formed, predict which is the major product. (a) CC1(Cl)CCCCC1 (b) ClCC1CCCCC1 (c) CC1(C)CCC(Cl)CC1

Short Answer

Expert verified
(a) Chloroalkane: CC1(Cl)CCCCC1 Major Product: C=C1CCCCC1 (b) Chloroalkane: ClCC1CCCCC1 Major Product: C=CCC1CCCCC1 (c) Chloroalkane: CC1(C)CCC(Cl)CC1 Major Product: CC1(C)CCC=C(C)C1

Step by step solution

01

Identifying \(\beta\)-Hydrogens

Look for the \(\beta\)-hydrogen atoms in the molecule that are adjacent to the carbon atom attached to the chlorine. In this case, there are two possible locations for the \(\beta\)-hydrogens.
02

Performing E2 Elimination Reaction

With sodium ethoxide being a strong base, applying the E2 mechanism, we would expect the major product to be the most stabilized alkene. In other words, the alkene with the most highly substituted double bond will be the major product.
03

Applying Zaitsev's Rule

According to Zaitsev's rule, the major product will be the alkene where the more substituted carbon is doubly bonded to one of the nearest \(\beta\)-hydrogens. In this case, the major product (major alkene) will be: C=C1CCCCC1 (b) ClCC1CCCCC1
04

Identifying \(\beta\)-Hydrogens

Locate the \(\beta\)-hydrogen atoms in the molecule that are adjacent to the carbon atom attached to the chlorine. In this case, there is only one possible location for the \(\beta\)-hydrogens.
05

Performing E2 Elimination Reaction

Apply the E2 mechanism with sodium ethoxide as the strong base, which leads us to predict the major product as the most stabilized alkene. In other words, the alkene with the most highly substituted double bond will be the major product.
06

Applying Zaitsev's Rule

According to Zaitsev's rule, the major product will be the alkene where the more substituted carbon is doubly bonded to one of the nearest \(\beta\)-hydrogens. In this case, the major product (major alkene) will be: C=CCC1CCCCC1 (c) CC1(C)CCC(Cl)CC1
07

Identifying \(\beta\)-Hydrogens

Find the \(\beta\)-hydrogen atoms in the molecule that are adjacent to the carbon atom attached to the chlorine. In this case, there is only one possible location for the \(\beta\)-hydrogens.
08

Performing E2 Elimination Reaction

Utilize the E2 mechanism with sodium ethoxide as the strong base, leading us to predict the major product as the most stabilized alkene. In other words, the alkene with the most highly substituted double bond will be the major product.
09

Applying Zaitsev's Rule

According to Zaitsev's rule, the major product will be the alkene where the more substituted carbon is doubly bonded to one of the nearest \(\beta\)-hydrogens. In this case, the major product (major alkene) will be: CC1(C)CCC=C(C)C1

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Most popular questions from this chapter

1-Chloro-4-isopropylcyclohexane exists as two stereoisomers: one cis and one trans. Treatment of either isomer with sodium ethoxide in ethanol gives 4 -isopropylcyclohexene by an E2 reaction. CC(C)C1CC=CCC1 1-Chloro-4- 4-Isopropylcyclohexene isopropylcyclohexane The cis isomer undergoes E2 reaction several orders of magnitude faster than the trans isomer. How do you account for this experimental observation?

\- Using your roadmap as a guide, show how to convert cyclohexane into racemic 3-bromocyclohexene. Show all reagents and all molecules synthesized along the way.

Attempts to prepare optically active iodides by nucleophilic displacement on optically active bromides using I \(\mathrm{I}^{-}\)normally produce racemic iodoalkanes. Why are the product iodoalkanes racemic?

Consider the following statements in reference to \(\mathrm{S}_{\mathrm{N}} 1, \mathrm{~S}_{\mathrm{N}} 2, \mathrm{E} 1\), and \(\mathrm{E} 2\) reactions of haloalkanes. To which mechanism (s), if any, does each statement apply? (a) Involves a carbocation intermediate. (b) Is first order in haloalkane and first order in nucleophile. (c) Involves inversion of configuration at the site of substitution. (d) Involves retention of configuration at the site of substitution. (e) Substitution at a stereocenter gives predominantly a racemic product. (f) Is first order in haloalkane and zero order in base. (g) Is first order in haloalkane and first order in base. (h) Is greatly accelerated in protic solvents of increasing polarity. (i) Rearrangements are common. (j) Order of reactivity of haloalkanes is \(3^{\circ}>2^{\circ}>1^{\circ}\). (k) Order of reactivity of haloalkanes is methyl \(>1^{\circ}>2^{\circ}>3^{\circ}\).

Suggest a product of the following reaction. HI is a very strong acid. $$ \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCH}_{2} \mathrm{CH}_{3}+2 \mathrm{HI} \longrightarrow $$
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