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 11.4, Problem 10P
After heating a solution of allyl tert-butyl sulfide and sodium ethoxide in ethanol for several hours, tert-butyl propenyl sulfide was isolated in
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Chapter 11 Solutions
Organic Chemistry - Standalone book
Ch. 11.1 - Prob. 1PCh. 11.1 - Prob. 2PCh. 11.2 - The two compounds shown differ by a factor of 60...Ch. 11.2 - Prob. 4PCh. 11.2 - Prob. 5PCh. 11.2 - Prob. 6PCh. 11.3 - Prob. 7PCh. 11.3 - Prob. 8PCh. 11.3 - Evaluate 2,3,3-trimethyl-1-butene as a candidate...Ch. 11.4 - After heating a solution of allyl tert-butyl...
Ch. 11.5 - Prob. 11PCh. 11.6 - Prob. 12PCh. 11.8 - Prob. 13PCh. 11.9 - What dienes containing isolated double bonds are...Ch. 11.10 - Prob. 15PCh. 11.10 - Prob. 16PCh. 11.11 - Prob. 17PCh. 11.12 - Dicarbonyl compounds such as quinones are reactive...Ch. 11.12 - 2,3-Di-tert-butyl-1,3-butadiene is extremely...Ch. 11.12 - Methyl acrylate (H2C=CHCO2CH3) reacts with...Ch. 11.13 - Prob. 21PCh. 11.14 - What diene and dienophile could you use to prepare...Ch. 11.14 - Write equations in the synthetic direction for the...Ch. 11.16 - Prob. 24PCh. 11.16 - Prob. 25PCh. 11 - Write structural formulas for each of the...Ch. 11 - Give an acceptable IUPAC name for each of the...Ch. 11 - A certain species of grasshopper secretes an...Ch. 11 - Which of the following are chiral?...Ch. 11 - Describe the molecular geometry expected for...Ch. 11 - Prob. 31PCh. 11 - What compound of molecular formula C6H10 gives...Ch. 11 - Prob. 33PCh. 11 - Prob. 34PCh. 11 - Prob. 35PCh. 11 - Prob. 36PCh. 11 - Identify the more reactive dienophile in each of...Ch. 11 - Prob. 38PCh. 11 - Prob. 39PCh. 11 - Prob. 40PCh. 11 - Prob. 41PCh. 11 - Prob. 42PCh. 11 - Prob. 43PCh. 11 - Prob. 44PCh. 11 - Prob. 45PCh. 11 - Prob. 46PCh. 11 - Show how to prepare each of the following...Ch. 11 - Prob. 48PCh. 11 - Prob. 49PCh. 11 - Prob. 50PCh. 11 - Compound A was converted to compound B by the...Ch. 11 - Suggest reasonable explanations for each of the...Ch. 11 - Prob. 53PCh. 11 - Prob. 54PCh. 11 - Prob. 55DSPCh. 11 - Prob. 56DSPCh. 11 - Prob. 57DSPCh. 11 - Prob. 58DSPCh. 11 - Prob. 59DSP
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- After heating a solution of allyl tert-butyl sulfide and sodium ethoxide in ethanol for several hours, tert-butyl propenyl sulfide was isolated in 66% yield. Suggest a stepwise mechanism for this isomerization. Which has the smaller pKa (is the stronger acid), the reactant or the product?arrow_forwardThe pKa values of a few ortho-, meta-, and para-substituted benzoic acids are shown below: The relative pKa values depend on the substituent. For chloro-substituted benzoic acids, the ortho isomer is the most acidic and the para isomer is the least acidic; for nitro-substituted benzoic acids, the ortho isomer is the most acidic and the meta isomer is the least acidic; and for amino-substituted benzoic acids, the meta isomer is the most acidic and the ortho isomer is the least acidic. Explain these relative acidities.a. Cl: ortho 7 meta 7 para b. NO2: ortho 7 para 7 meta c. NH2: meta 7 para 7 orthoarrow_forwardThe pKa values of a few ortho-, meta-, and para-substituted benzoic acids are shown below: The relative pKa values depend on the substituent. For chloro-substituted benzoic acids, the ortho isomer is the most acidic and the para isomer is the least acidic; for nitro-substituted benzoic acids, the ortho isomer is the most acidic and the meta isomer is the least acidic; and for amino-substituted benzoic acids, the meta isomer is the most acidic and the ortho isomer is the least acidic. Explain these relative acidities. a. Cl: ortho > meta > para b. NO2: ortho > para > meta c. NH2: meta > para > orthoarrow_forward
- Propanal and propanone react in a similar way with acidified aqueous potassium cyanide, KCN. For this reaction to occur reasonably quickly, the pH of the solution should be approximately 4. The reaction of propanal proceeds with acidified potassium cyanide proceeds more rapidly than that of propanone. Referring to the mechanism of the reactions, explain this phenomenon.arrow_forwardThe pKa of phenol is 10.0 and the pKa of para-nitrophenol is 7.2. Given this information, one knows that The conjugate base of para-nitrophenol must be less stable than the conjugate base of phenol The conjugate acid of para-nitrophenol must be more stable than the conjugate base of phenol The conjugate base of para-nitrophenol must be more stable than the conjugate base of phenol Both acids are basesarrow_forwardArrange the following compounds in the increasing order of their acid strength: p-cresol, p-nitrophenol, phenolarrow_forward
- 4) Write the reaction between cyclohexanecarboxylic acid and thionyl chloride showing all three products (two gaseous and one liquid). Take the liquid product and treat it with 2 moles of dimethylamine in benzene as the solvent. You get two products. What are they? Draw their formulae and write their names.arrow_forwardThe following three derivatives of succinimide are anticonvulsants that have found use in the treatment of epilepsy, particularly petit mal seizures. Q. Of these three anticonvulsants, one is considerably more acidic than the other two. Which is the most acidic compound? Estimate its pKa and account for its acidity. How does its acidity compare with that of phenol? with that of acetic acid?arrow_forwardQ5:- Give structures and names of the principal organic reactants and products of the following reactions. a- pentinoic acid from butanol b- Preparation of acid anhydrides Q6:- Rank the following substances in order of increasing acidity , Justify your choice. benzoic acid, p-chlorobenzoic acid , 2,4-dichlorobenzoic acid , 2,4,6-trichlorobenzoic acidarrow_forward
- Isoerythrogenic acid, C18H26O2, is an acetylic fatty acid that turns a vivid blue on exposure to UV light. On Catalytic hydrogenation over a palladium catalyst, five molar equivalents of hydrogen are absorbed, and stearic acid, CH3(CH2)16CO2H, is produced. Ozonolysis of isoerythrogenic acid yields the following products: formaldehyde, CH2O, malonic acid, HO2CCH2CO2H, adipic acid, HO2C(CH2)4CO2H, and the aldehyde carboxylic acid, OHC(CH2)6CO2H. Provide a structure for isoerythrogenic acid.arrow_forwardPyridine forms a stronger Lewis acid-base complex with SO3 than SO2. However, pyridine forms a weaker complex with SF6 than with SF4. Explain the difference.arrow_forwardWhy are carboxylic acids more acidic than alcohols? The increased inductive effect of the alkyl group of the carboxylic acid resonance stabilization of the carboxylate ion (conjugate base of carboxylic acids) Due to hydrogen bonding They have high pKa valuesarrow_forward
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