Concept explainers
The heats of combustion of the more and less stable stereoisomers of the
and
Dimethylcyclohexane
Heats of combustion (kJ/mol):
More stable stereoisomer
Less stable stereoisomer
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Solutions Manual for Organic Chemistry
- Write a conformational structure for 1,2,3-trimethylcyclohexane in which all the methyl groups are axial and then show its more stable conformation.arrow_forwardWhich will be more stable, cis or trans-1,4-tert-butylcyclohexane? Explain by drawing their structures?arrow_forwardOn a cyclohexane ring, an axial carboxyl group has a conformational energy of 5.9 kJ (1.4 kcal)/mol relative to an equatorial carboxyl group. Consider the equilibrium for the alternative chair conformations of trans-1,4-cyclohexanedicarboxylic acid. Draw the less stable chair conformation on the left of the equilibrium arrows and the more stable chair on the right. Calculate DG0 for the equilibrium as written and calculate the ratio of the more stable chair to the less stable chair at 25°C.arrow_forward
- From : cis (1s, 4s) -1-bromo- (tert-butyl) cyclohexane trans (1r, 4r)- 1- iodo- 4- isoproppylcyclohexane 1,5 - dimethylcyclohex -1 -ene trans (1r, 4r)- (tert - butyl) - 4- fluorocyclohexane trans (1r, 4r) - 1- bromo - 4- (tert - butyl) cyclohexane 1,3,5 - trimethylcyclohex - 1- ene . 5- Choose the substrate from the ones that drawn and illustrate an example complete Markovnikov addition mechanism using the reagents of your choice showing all stereochemical consequences. Identify if your addition mechanism is syn addition or anti addiction (Use curved arrows to show the electron movement in everyday steps). use ChemDraw if possible..arrow_forwardIllustrate the differences between stereoisomers and conformations in a 1,3-diene: ?arrow_forwardFrom studies of the dipole moment of 1,2-dichloroethane in the gas phase at room temperature (25°C), it is estimated that the ratio of molecules in the anti conformation to gauche conformation is 7.6 to 1. Calculate the difference in Gibbs free energy between these two conformations.arrow_forward
- Solve for the value of x in the following combustion reaction of a particular alkane in the presence of heat, CH3(CH2)xCH3 + yO2 → zCO2 + 14 H2O A. 4 B. 3 C. 15 D. 11 E. 5arrow_forwardGibbs free energy differences between axial-substituted and equatorial-substituted chair conformations of cyclohexane were given in Table 2.4. (a) Calculate the ratio of equatorial to axial tert-butylcyclohexane at 25C. (b) Explain why the conformational equilibria for methyl, ethyl, and isopropyl substituents are comparable but the conformational equilibrium for tert-butylcyclohexane lies considerably farther toward the equatorial conformation.arrow_forward1,4-Pentadiene (CH2=CH-CH2-CH=CH2) is a liquid at room temperature and has a density of 0.66 g/mL and molar mass of 68.12 g/mol. In a laboratory experiment, 3.80 mL of this compound was treated with 4.80 mL of conc. H2SO4 (100% w/w; molar mass 98.08 g/mol). Note that the density of conc. H2SO4 is 1.84 g/mL. The resulting sulfate ester was then treated with 1.20 mL of water (molar mass 18.02 g/mol) affording, after work- up, 2,4-pentanediol (molar mass 104.15 g/mol) as the crude product. The crude product was then purified by simple distillation, which yielded 2.00 g of pure product. What is the theoretical yield of 2,4-pentanediol expressed in grams? Show calculations. What is the percentage yield of pure 2,4-pentanediol?arrow_forward
- 1,4-Pentadiene (CH2=CH-CH2-CH=CH2) is a liquid at room temperature and has a density of 0.66 g/mL and molar mass of 68.12 g/mol. In a laboratory experiment, 3.80 mL of this compound was treated with 4.80 mL of conc. H2SO4 (100% w/w; molar mass 98.08 g/mol). Note that the density of conc. H2SO4 is 1.84 g/mL. The resulting sulfate ester was then treated with 1.20 mL of water (molar mass 18.02 g/mol) affording, after work- up, 2,4-pentanediol (molar mass 104.15 g/mol) as the crude product. The crude product was then purified by simple distillation, which yielded 2.00 g of pure product. a. Provide a balanced chemical equation to show the reaction between 1,4-pentadiene and sulfuric acid. Do not use molecular formulas in the chemical equation except for sulfuric acid. b. What reactant is the limiting reagent in this chemical equation? Show calculations to support your answer.arrow_forwardHow many products of 2-hexene+Cl2 are therearrow_forwardIn addition to more highly fluorinated products, fluorination of 2-methylbutane yields a mixture of compounds with the formula C5H10F2. Draw the structures of all the isomers with the formula C5H10F2 that would be produced and label with a star all the chiral centers present in their structures.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning