Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 8, Problem 41P
Interpretation Introduction
Interpretation:
The reason why the double bond of tetrachloroethene is undetectable in the bromine test for unsaturation is to be explained.
Concept Introduction:
Bromination leads to the addition reaction of
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Why does the addition of bromine to fumaric acid require a high temperature for the reaction while other substrates (generic alkanes, alkenes, and alkynes) react with bromine at room temperature?
b) i) Draw the different structural isomers of the 6-membered ring compound
[GAAIBNPAS]H6 in which there are alternating Group 13 and 15 elements.
ii) The isomers containing both B-N and AI-N bonding are the most stable.
Explain why this is the case.
ii) How would you expect the structure and reactivity of the heterocycles
[GAAIBNPAS]H6 to compare with borazine?
iv) While borazine exists as a planar ring compound, the [GAAIBNPAS]H6 ring
compounds dimerize. Explain these observations.
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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%
87%
benzaldehyde → stilbene → stilbene dibromide
41%
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 8 Solutions
Organic Chemistry
Ch. 8 - Prob. 1PPCh. 8 - Prob. 2PPCh. 8 - Practice Problem 8.3 Provide mechanistic...Ch. 8 - Prob. 4PPCh. 8 - Prob. 5PPCh. 8 - Prob. 6PPCh. 8 - Prob. 7PPCh. 8 - Prob. 8PPCh. 8 - Prob. 9PPCh. 8 - Prob. 10PP
Ch. 8 - Prob. 11PPCh. 8 - Prob. 12PPCh. 8 - Practice Problem 8.13
Specify the appropriate...Ch. 8 - Prob. 14PPCh. 8 - Practice Problem 8.15 Write a mechanism to explain...Ch. 8 - Prob. 16PPCh. 8 - Prob. 17PPCh. 8 - Prob. 18PPCh. 8 - Practice Problem 8.19 Treating cyclohexene with l,...Ch. 8 - Prob. 20PPCh. 8 - Practice Problem 8.21
Predict the products of the...Ch. 8 - Prob. 22PPCh. 8 - Prob. 23PPCh. 8 - Prob. 24PPCh. 8 - Prob. 25PPCh. 8 - Write structural formulas for the products that...Ch. 8 - Prob. 27PCh. 8 - Prob. 28PCh. 8 - 8.29. Give the structure of the products that you...Ch. 8 - Give the structure of the products you would...Ch. 8 - Prob. 31PCh. 8 - Prob. 32PCh. 8 - Prob. 33PCh. 8 - Prob. 34PCh. 8 - Prob. 35PCh. 8 - Prob. 36PCh. 8 - Prob. 37PCh. 8 - When 3, 3-dimethyl-2-butanol is neared with...Ch. 8 - Prob. 39PCh. 8 - Prob. 40PCh. 8 - Prob. 41PCh. 8 - Prob. 42PCh. 8 - 8.43. Write a mechanism that explains the...Ch. 8 - 8.44. Write a mechanism for the following...Ch. 8 - Write a mechanism that explains formation of the...Ch. 8 - Prob. 46PCh. 8 - 8.47. Farnesene (below) is a compound found in the...Ch. 8 - Limonene is a compound found in orange oil and...Ch. 8 - Prob. 49PCh. 8 - Synthesize the following compound starting with...Ch. 8 - Predict features of their IR spectra that you...Ch. 8 - Deduce the structures of compounds A, B, and C,...Ch. 8 - Ricinoleic acid, a compound that can be isolated...Ch. 8 - 8.54. There are two dicarboxylic acids with the...Ch. 8 - Prob. 55PCh. 8 - Prob. 56PCh. 8 - Prob. 57PCh. 8 - Prob. 58PCh. 8 - 8.59. For each of the following questions, please...Ch. 8 - Prob. 60PCh. 8 - Prob. 61PCh. 8 - Prob. 62PCh. 8 - Triethylamine, (C2H5)3N, like all amines, has a...Ch. 8 - (a) Synthesize (3S, 4R)-3,...Ch. 8 - Prob. 2LGPCh. 8 - Prob. 3LGPCh. 8 - Prob. 4LGP
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- When 30 cm3 of a gaseous hydrocarbon was exploded with 210cm3 of oxygen the residual gases occupied volume of 150cm3. After shaking the residual gases with excess aqueous sodium hydroxide, the final volume was 30cm3.(All volumes were measured at room temperature and pressure.) The hydrocarbon has a number of isomers. Draw the displayed formulae and name 2 of the isomers of the hydrocarbon that illustrate each of the following types of isomerism below (i.e. 2 isomers must be drawn for each type of isomerism) (i) chain (ii)functional grouparrow_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_forward1) Discuss three methods that can be utilised to synthesise n – heptane in the laboratory.arrow_forward
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- 1. Write the structure of the aminal or hemiaminal intermediate and the imine product formed in the reaction of Acetaldehyde and benzylamine, C6HSCH2NH2. 2. Write the structure of the hemiaminal intermediate and the enamine product formed in the reaction of 3-Pentanone and pyrrolidine. 3. Identify the alkene formed in the following reaction 'H. (CeHs)»P- 4. Predict the principal organic product for the following reaction. K2Cr2O7 H2SO4, H20 H. 5. What is the expected chemical shift for the aldehyde hydrogen in 'H NMR and aldehyde carbon in 13C NMR?arrow_forwardGive the structural chemistry of active methylene, classify it asradical/intermediate/stable organic compound, reagent of its production and role in alkylationarrow_forwardBiphenyl has the following structure.(a) Is biphenyl a (fused) polynuclear aromatic hydrocarbon?(b) How many pi electrons are there in the two aromatic rings of biphenyl? How does this number compare with that for naphthalene?(c) The heat of hydrogenation for biphenyl is about 418 kJ>mol (100 kcal>mol). Calculate theresonance energy of biphenyl.(d) Compare the resonance energy of biphenyl with that of naphthalene and with that of two benzene rings. Explain thedifference in the resonance energies of naphthalene and biphenyl.arrow_forward
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