Based on the data below, what is the reactivity order of the following compounds? Explain your reasoning in detail. Chlorobenzene Total: 327mg Ortho: 162mg / Para: 165mg Bromobenzene Total: 508mg Ortho: 128mg / Para: 380mg Iodobenzene Total: 664mg Ortho: 20mg / Para: 664mg

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter13: Substitution
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Based on the data below, what is the reactivity order of the following compounds? Explain your reasoning in detail.

Chlorobenzene

Total: 327mg

Ortho: 162mg / Para: 165mg

Bromobenzene

Total: 508mg

Ortho: 128mg / Para: 380mg

Iodobenzene

Total: 664mg

Ortho: 20mg / Para: 664mg

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Which position of substitution (ortho or para) is favored for iodobenzene, bromobenzene and chlorobenzene in F-C acylation? and why?

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What would be the mechanism for the acylation of iodobenzene to form the major product with the data above?

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Follow-up Question

Is there a trend in the ortho: para product ratios as the substituent on the benzene ring changes, based on the data? Describe the trend in the ortho: para product ratios in relation to a chemical principle, if any exist.

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