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 SAPLING ACCESS + ETEX
- SH 0arrow_forward2. Please consider the two all 'cis' isomers of trimethylcyclohexane drawn below. Draw the two chair conformers of each stereoisomer below (1 and 2) and calculate their torsional interaction energies in order to identify the lower energy conformer for each stereoisomer. Based on your calculations, state which of the two stereoisomers 1 and 2 is less stable and which is more stable. [1,3-diaxial CH3 CH3 = 3.7kcal/mol; 1,3-diaxial CH3 H = 0.88kcal/mol; cis-1,2 (axial:equatorial) CH3 CH3 = 0.88kcal/mol; trans-1,2-diequatorial CH3 CH3 = 0.88kcal/mol) all-cis-1,2,3- 1 all-cis-1,2,4- 2arrow_forwardNonearrow_forward
- What is the mechanism by which the 1,4 product is created? Please draw it by hand with arrows and stuff.arrow_forwardWhat is the relationship between A and B? H3C A Br Cl H3C B Br relationship (check all that apply) O same molecule O enantiomer O diastereomer structural isomer O stereoisomer isomer O need more information to decide O same molecule ☐ enantiomer Br Br Br CH3 Br CI CH3 O diastereomer ☐ structural isomer ☐ stereoisomer isomer O need more information to decide O same molecule O enantiomer Odiastereomer structural isomer O stereoisomer ☐ isomer O need more information to decidearrow_forwardb. Please complete the zig-zag conformation of the compound (3R,4S)-3,4-dichloro-2,5-dimethylhexane by writing the respective atoms in the boxes. 4arrow_forward
- c. Serricornin, the female-produced sex pheromone of the cigarette beetle, has the following structure. OH What is the maximum number of possible stereoisomers? Is this structure a meso compound? d. Please consider the natural product alkaloids shown below. Are these two structures enantiomers, diastereomers or conformers? H HO H H HN HO HN R R с R=H cinchonidine R=ET cinchonine Harrow_forwardNail polish remover containing acetone was spilled in a room 5.23 m × 3.28 m × 2.76 m. Measurements indicated that 2,250 mg of acetone evaporated. Calculate the acetone concentration in micrograms per cubic meter.arrow_forwardPlease help me answer number 1. 1. If your graphs revealed a mathematical relationship between specific heat and atomic mass, write down an equation for the relationship. I also don't understand, is the equation from the line regression the one that I'm suppose use to show the relationship? If so could you work it all the way out?arrow_forward
- Describe the principle of resonance and give a set of Lewis Structures to illustrate your explanation.arrow_forwardDon't used hand raitingarrow_forwardIt is not unexpected that the methoxyl substituent on a cyclohexane ring prefers to adopt the equatorial conformation. OMe H A G₂ = +0.6 kcal/mol OMe What is unexpected is that the closely related 2-methoxytetrahydropyran prefers the axial conformation: H H OMe OMe A Gp=-0.6 kcal/mol Methoxy: CH3O group Please be specific and clearly write the reason why this is observed. This effect that provides stabilization of the axial OCH 3 group in this molecule is called the anomeric effect. [Recall in the way of example, the staggered conformer of ethane is more stable than eclipsed owing to bonding MO interacting with anti-bonding MO...]arrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning