VMun54

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What are the rules regarding reactivity of cycloalkyl halides. I had a question on the destroyer #108 that asked to rank compounds in order of reactivity. The tertiary cyclic alkyl halide was chosen over as the most reactive, followed by a secondary cyclic alkyl halide and a primary alkyl halide

Are there rules to reactivity of substitution or elimination reactions regarding this?? I couldnt find much online. Thanks
 

orgoman22

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What are the rules regarding reactivity of cycloalkyl halides. I had a question on the destroyer #108 that asked to rank compounds in order of reactivity. The tertiary cyclic alkyl halide was chosen over as the most reactive, followed by a secondary cyclic alkyl halide and a primary alkyl halide

Are there rules to reactivity of substitution or elimination reactions regarding this?? I couldnt find much online. Thanks
Here is a good general rule system .........Tertiary halides love to do elimination reactions....especially if heat or a strong nucleophile is added. Next is secondary......then finally primary. Primary halides usually do SN2 reactions unless a strong sterically hindered base such as LDA or t-butoxide is employed. Then, the E2 will result. Next......if you have two secondary halides, look at the leaving group. Iodides are awesome leaving groups.....bromides are pretty good.....chlorides are fair...and fluorides are poor. Problem #108 will be more enjoyable now that you know what you are doing.

Keep up the great work.

Hope this helps

Dr. Jim Romano
 
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VMun54

2+ Year Member
Dec 5, 2016
44
10
Status
Dental Student
Here is a good general rule system .........Tertiary halides love to do elimination reactions....especially if heat or a strong nucleophile is added. Next is secondary......then finally primary. Primary halides usually do SN2 reactions unless a strong sterically hindered base such as LDA or t-butoxide is employed. Then, the E2 will result. Next......if you have two secondary halides, look at the leaving group. Iodides are awesome leaving groups.....bromides are pretty good.....chlorides are fair...and fluorides are poor. Problem #108 will be more enjoyable now that you know what you are doing.

Keep up the great work.

Hope this helps

Dr. Jim Romano
Thanks Dr. Romano, that helped !
 
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