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4. The cis isomer of 4-tert-butyl-1-bromocyclohexane undergoes E2 eliminations about 1,000 times faster than the trans isomer. Explain why the cis isomer reacts fast in complete sentences. (Hint: Draw the most stable chair structure of each; it is not because of steric hindrance.) Br Br NaOH FAST NaOH SLOW

4. The cis isomer of 4-tert-butyl-1-bromocyclohexane undergoes E2 eliminations about 1,000 times faster than the trans isomer. Explain why the cis isomer reacts fast in complete sentences. (Hint: Draw the most stable chair structure of each; it is not because of steric hindrance.) Br Br NaOH FAST NaOH SLOW

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Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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**Question 4** The cis isomer of 4-tert-butyl-1-bromocyclohexane undergoes E2 eliminations about 1,000 times faster than the trans isomer. Explain why the cis isomer reacts fast in complete sentences. (Hint: Draw the most stable chair structure of each; it is not because of steric hindrance.) **Reaction Diagrams:** 1. **Cis Isomer Reaction:** - Structure: A cyclohexane ring with a bromine (Br) atom and a tert-butyl group both in an equatorial position on the same side. - Reaction condition: Under the influence of NaOH. - Outcome: The reaction proceeds fast, leading to the formation of a cyclohexene product. 2. **Trans Isomer Reaction:** - Structure: A cyclohexane ring with a bromine (Br) atom in an axial position and a tert-butyl group in an equatorial position on opposite sides. - Reaction condition: Under the influence of NaOH. - Outcome: The reaction proceeds slowly and also leads to the formation of a cyclohexene product. **Explanation:** The faster reaction rate of the cis isomer is due to the geometric alignment favorable for the E2 mechanism, where the leaving group (Br) and the hydrogen to be extracted must be antiperiplanar. The equatorial positions in the cis isomer facilitate this alignment, unlike in the trans isomer, where the arrangement is less favorable for E2 elimination. This is not attributed to steric hindrance but rather to the proper geometric configuration for effective elimination.
Transcribed Image Text:**Question 4** The cis isomer of 4-tert-butyl-1-bromocyclohexane undergoes E2 eliminations about 1,000 times faster than the trans isomer. Explain why the cis isomer reacts fast in complete sentences. (Hint: Draw the most stable chair structure of each; it is not because of steric hindrance.) **Reaction Diagrams:** 1. **Cis Isomer Reaction:** - Structure: A cyclohexane ring with a bromine (Br) atom and a tert-butyl group both in an equatorial position on the same side. - Reaction condition: Under the influence of NaOH. - Outcome: The reaction proceeds fast, leading to the formation of a cyclohexene product. 2. **Trans Isomer Reaction:** - Structure: A cyclohexane ring with a bromine (Br) atom in an axial position and a tert-butyl group in an equatorial position on opposite sides. - Reaction condition: Under the influence of NaOH. - Outcome: The reaction proceeds slowly and also leads to the formation of a cyclohexene product. **Explanation:** The faster reaction rate of the cis isomer is due to the geometric alignment favorable for the E2 mechanism, where the leaving group (Br) and the hydrogen to be extracted must be antiperiplanar. The equatorial positions in the cis isomer facilitate this alignment, unlike in the trans isomer, where the arrangement is less favorable for E2 elimination. This is not attributed to steric hindrance but rather to the proper geometric configuration for effective elimination.
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