Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 13.10, Problem 13P
Interpretation Introduction
Interpretation:
The given parts with respect to
Concept Introduction:
The rate of electrophilic
The presence of a substituent on benzene ring modifies the rates at which EAS occurs at different ring carbons.
The rate of EAS depends on the position of the carbon relative to the substituent already present and the number of equivalent carbons of each type.
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Explain how Hammond's postulate accounts for the higher
selectivity of bromination reactions as compared to chlorination
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Bromocyclopentane is more reactive than bromocyclohexane when heated with sodium iodide in acetone. Explain this difference in reactivity.
Assuming that benzaldehyde is the limiting reagent for the synthesis of stilbene, that stilbene is the limiting reagent for the synthesis of stilbene dibromide, and that stilbene dibromide
is the limiting reagent for the synthesis of diphenylacetylene; what is the overall % yield of diphenylacetylene from benzaldehyde given the percentage yield of each step of the
reaction sequence as follows? Give only two significant digits. If the answer is a whole number with two digits, do not include the decimal.
52%
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Answer:
diphenylacetylene
Notes:
For our multi-step synthesis we cannot just calculate the yield based on starting amount of benzaldehyde and final amount of diphenylacetylene because your group may have been
supplemented with commercial material at one or more steps.
In truth most chemist use an excess of the least expensive reagent to increase their yield. So in our case benzyltriphenylphosphonium chloride should probably be our…
Chapter 13 Solutions
Organic Chemistry - Standalone book
Ch. 13.2 - Based on Hammonds postulate which holds that the...Ch. 13.3 - Prob. 2PCh. 13.3 - Using : O =N+= O : as the electrophile, write a...Ch. 13.4 - Prob. 4PCh. 13.5 - Prob. 5PCh. 13.6 - Prob. 6PCh. 13.6 - Write a reasonable mechanism for the formation of...Ch. 13.6 - tert-Butylbenzene can be prepared by alkylation of...Ch. 13.6 - Prob. 9PCh. 13.7 - The reaction shown gives a single product in 88...
Ch. 13.7 - Prob. 11PCh. 13.8 - Using benzene and any necessary organic or...Ch. 13.10 - Prob. 13PCh. 13.11 - Prob. 14PCh. 13.12 - Prob. 15PCh. 13.12 - Prob. 16PCh. 13.13 - Prob. 17PCh. 13.13 - Prob. 18PCh. 13.14 - Reaction of chlorobenzene with p-chlorobenzyl...Ch. 13.15 - Prob. 20PCh. 13.15 - Prob. 21PCh. 13.15 - Prob. 22PCh. 13.16 - Prob. 23PCh. 13.16 - Prob. 24PCh. 13.17 - Prob. 25PCh. 13.18 - Prob. 26PCh. 13.19 - Write the structure of the expected product from...Ch. 13.20 - Prob. 28PCh. 13.20 - Prob. 29PCh. 13.21 - Prob. 30PCh. 13.21 - Offer an explanation for the observation that...Ch. 13.21 - Prob. 32PCh. 13 - Write the structure of the organic product in each...Ch. 13 - Prob. 34PCh. 13 - Prob. 35PCh. 13 - Prob. 36PCh. 13 - Prob. 37PCh. 13 - Prob. 38PCh. 13 - Prob. 39PCh. 13 - Treatment of the alcohol shown with sulphuric acid...Ch. 13 - Prob. 41PCh. 13 - Prob. 42PCh. 13 - Prob. 43PCh. 13 - Arrange the following five compounds in order of...Ch. 13 - Prob. 45PCh. 13 - Prob. 46PCh. 13 - Prob. 47PCh. 13 - Give reagents suitable for carrying out each of...Ch. 13 - Prob. 49PCh. 13 - Prob. 50PCh. 13 - Which is the best synthesis of the compound shown?Ch. 13 - What combination of acyl chloride or acid...Ch. 13 - A standard synthetic sequence for building a...Ch. 13 - Prob. 54PCh. 13 - Prob. 55PCh. 13 - Prob. 56PCh. 13 - Prob. 57PCh. 13 - Prob. 58PCh. 13 - Prob. 59PCh. 13 - Prob. 60DSPCh. 13 - Prob. 61DSPCh. 13 - Prob. 62DSPCh. 13 - Prob. 63DSP
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- Explain with the help of electronic effects, ‘generally haloalkenes undergo nucleophilic substitution reactions whereas haloarenes undergo electrophilic substitution reactions’.arrow_forwardAssuming that benzaldehyde is the limiting reagent for the synthesis of stilbene, that stilbene is the limiting reagent for the synthesis of stilbene dibromide, and that stilbene dibromide is the limiting reagent for the synthesis of diphenylacetylene; what is the overall % yield of diphenylacetylene from benzaldehyde given the percentage yield of each step of the reaction sequence as follows? Give only two significant digits. If the answer is a whole number with two digits, do not include the decimal. benza Idehy de Notes: 66% stil be ne 23% stilbene dibromi de 66% dipheny lacetyle nearrow_forwardPossible alternative brominations include: Veratrole (1,2-dimethoxybenzene) to 1,2-dibromo-4,5-dimethoxybenzene; 4-Methylacetanilide to 2-bromo-4-methylacetanilide; 2-Methylacetanilide (made in experiment S.1) to 4-bromo-2-methylacetanilide; Vanillin to 5-bromovanillin; Acetanilide to 4-bromoacetanilide; a. b. C. d. e. EXPERIMENT S4: BROMINATION OF AROMATIC COMPOUNDS Certain other acetanilides made in experiment S.1 may also be used as precursors in this experiment. Estimated time: 1 afternoon Associated learning goals: Section 6, LG 6.6; Section 7, LG 7.2 and 7.4 Pre-lab report: complete the standard report form, and answer the following questions. In this experiment, molecular bromine (Br2) is generated from the redox reaction of potassium bromate with hydrobromic acid. Write a balanced equation for this process. Briefly outline the mechanism by which Br2 brominates your aromatic compound. Why do the bromine atoms end up at the positions indicated rather than anywhere else in the…arrow_forward
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