Concept explainers
(a)
Interpretation:
The structure for each of the given thioesters.
Concept Introduction:
Thioesters are sulfur analogs of esters. The S-alkyl or S-aryl thioester has a carbonyl group and a sulfur-linked alkyl or aryl group. The first part of the name indicates that the alkyl or aryl group has bonded to the sulfur atom. The last part of the name indicates the
Answer to Problem 25.1P
Explanation of Solution
In the given name cyclohexyl thiobenzoate, the cyclohexyl is the alkyl group which is bonded to the sulfur atom. Thiobenzoate consists of a phenyl ring bonded to the sulfur atom through a carbonyl group. The structure for cyclohexyl thiobenzoate is drawn as below:
The structure for cyclohexyl thiobenzoate is:
(b)
Interpretation:
The structure for each of the given thioesters.
Concept Introduction:
Thioesters are sulfur analogs of esters. The S-alkyl or S-aryl thioester has a carbonyl group and a sulfur-linked alkyl or aryl group. The first part of the name indicates that the alkyl or aryl group has bonded to the sulfur atom. The last part of the name indicates the carboxylic acid stem. In common usage, the “S-“prefix is understood, and so, it is not mentioned.
Answer to Problem 25.1P
Explanation of Solution
The first part of the name suggests that the isopropyl group must be attached directly to the sulfur atom. The second part of the name suggests that the ester is formed from butanoic acid. In
The structure for S-isopropyl butanethioate is:
(c)
Interpretation:
The structure for each of the given thioesters.
Concept Introduction:
Thioesters are sulfur analogs of esters. The S-alkyl or S-aryl thioester has a carbonyl group and a sulfur-linked alkyl or aryl group. The first part of the name indicates that the alkyl or aryl group has bonded to the sulfur atom. The last part of the name indicates the carboxylic acid stem. In common usage, the “S-“prefix is understood, and so, it is not mentioned.
Answer to Problem 25.1P
Explanation of Solution
The first part of the name suggests that the phenyl ring must be attached directly to the sulfur atom. The second part of the name suggests that the ester is formed from the carboxylic acid which contains a cyclohexyl ring. In IUPAC nomenclature, “thio-“is inserted before the “ate” suffix in the name of the corresponding oxygen ester.
The structure for S-phenyl cyclohexanecarbothioate is shown as below:
The structure for S-phenyl cyclohexanecarbothioate is:
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Chapter 25 Solutions
Organic Chemistry
- Calculate activation energy (Ea) from the following kinetic data: Temp (oC) Time (s) 23.0 180. 32.1 131 40.0 101 51.8 86.0 choices: 0.0269 kJ/mole 2610 kJ/mole 27.6 kJ/mole 0.215 kJ/mole 20.8 kJ/molearrow_forwardCalculate activation energy (Ea) from the following kinetic data: Temp (oC) Time (s) 23.0 180. 32.1 131 40.0 101 51.8 86.0arrow_forwardDon't used hand raiting and don't used Ai solutionarrow_forward
- Rank the compounds in each group below according to their reactivity toward electrophilic aromatic substitution (most reactive = 1; least reactive = 3). Place the number corresponding to the compounds' relative reactivity in the blank below the compound. a. CH₂F CH3 F b. At what position, and on what ring, is bromination of phenyl benzoate expected to occur? Explain your answer. :0: C-O phenyl benzoate 6.Consider the reaction below to answer the following questions. A B C NO₂ FeBr3 + Br₂ D a. The nucleophile in the reaction is: BODADES b. The Lewis acid catalyst in the reaction is: C. This reaction proceeds d. Draw the structure of product D. (faster or slower) than benzene.arrow_forwardPart 2. A solution of 6.00g of substance B in 100.0mL of aqueous solution is in equilibrium, at room temperature, wl a solution of B in diethyl ether (ethoxyethane) containing 25.0 g of B in 50.0 mL 9) what is the distribution coefficient of substance B b) what is the mass of B extracted by shaking 200 ml of an aqueous solution containing 10g of B with call at room temp): i) 100 mL of diethyl ether ii) 50ml of diethyl ether twice iii) 25ml of diethyl ether four timesarrow_forward- Rank the following groups of compounds from most acidic (1) to least acidic (4). Place the number corresponding to the compound's relative rank in the blank below the structure. a. NO₂ NO₂ CH2CH2CH2CH2OH CH3 CH3CH2CHOH CH3CH2CH2CH2OH NO₂ CH3CHCH2CH2OH b. OH OH CH₂OH CO₂H HC CN CN CNarrow_forward
- Give the major organic product(s) of the following reactions or sequences of reactions. Show all relevant stereochemistry a. H MgBr 1. ether 2. H₂O* 4 COH b. 1. LIAIH, ether 2. H₂O Choose the best reagent(s) for carrying out the following conversions from the list provided below. Place the letter of the best choice in the blank to the left of the conversion. Reagents may be used more than once. a. 1. CH3MgBr, ether 2. H3O+ NaOH b. 1. PBr3 2. C. 2. 1. (CH3)3SiCl, (CH3CH2)3N CH3MgBr, ether 3. H₂O*+ 2. H3O+ e. 1. p-TosCl, pyridine f. نها g. 2. NaOH CrO3, H₂SO4, H₂O 1. NaBH4, ethanol 2. H30* h. PCC, CH2Cl2 Ovoldo-6 a. b. OH OH H OH O any organicarrow_forwardDetermine the rate law for sodium thiosulfate from the following data: [Na2S2O3] Time (s) 0.0318 230. 0.0636 57.5arrow_forwardDon't used hand raiting and don't used Ai solutionarrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning