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- (A)Menthol, used to flavor various foods and tobacco, is the most stable stereoisomer of 2-isopropyl-5-methylcyclohexanol. Draw its most stable conformation. Is the hydroxyl group cis or trans to the isopropyl group? To the methyl group? (b) Neomenthol is a stereoisomer of menthol. That is, it has the same constitution but differs in the arrangement of its atoms in space. Neomenthol is the second most stable stereoisomer of 2-isopropyl-5methylcyclohexanol; it is less stable than menthol but more stable than any other stereoisomer. Write the structure of neomenthol in its most stable conformation.Classify the double bonds in the following compounds as cumulated, conjugated or isolated. I-cumulated, II conjugated 1-cumulated: 11-isolated I-conjugated: II-isolated 1-isolated; Il-cumulated 01-conjugated: Il-cumulated -8Gibbs 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.
- Fill in the blanks: cis-1,3-Dimethylcyclohexane has two different chair conformations: one withboth methyl groups in __________ positions and one with both methyl groups in ____________ positions.Ketones react with alcohols to yield products called acetals. Why does the all-cis isomer of 4-tert-butyl-1,3-cyclohexanediol react readily with acetone and an acid catalyst to form an acetal, but other stereoisomers do not react? In formulating your answer, draw the more stable chair conformations of all four stereoisomers and the product acetal for each one.Use your answers from Problem 2.48 to complete the table showing correlations between cis,trans and axial,equatorial for disubstituted derivatives of cyclohexane. Draw the alternative chair conformations for the cis and trans isomers of 1,2-dimethylcyclohexane, 1,3-dimethylcyclohexane, 1,4-dimethylcyclohexane. (a) Indicate by a label whether each methyl group is axial or equatorial.
- H3C HC 10 aH CH3 In its most stable chair conformation, indicate the orientation of each of the labeled groups in this substituted cyclohexane. Group a: Group b: Group c:1. Name compounds by IUPAC nomenclature CH₂CH-COOH a ОН 2) Find all of the heterofunctional compounds among following: ОН 2 сн, -ен, -с NH, OH COOH CH-OH CH,COOH e b COOH H-C-OH н-с- -ОН COOH -СООН f с H₂C-C-CH₂ 0 COOH HO-C-CH,COOH CH,COOH CH2-CH-CH2; OH ОН ОН g d ОН HOOC–C–CH,COOH ОН HOỌC –COOH б ONaPage of 11 ZOOM + A1. What is the arrangement of the bonds surrounding carbon in a saturated hydrocarbon? linear trigonal planar tetrahedral В trigonal bipyramidal A2. What is the definition of a constitutional isomer? A molecules with the same numbers and kinds of atoms arranged in different ways molecules with the same arrangements of atoms, but different arrangements of electrons molecules with the same connectivities, but different 3-D angles molecules with different isotopes of the same atoms В АЗ. How many hydrogen atoms does the following molecule contain? 12 В 16 18 Which functional group gives rise to a broad IR absorption between 3200 cm-1 and 3600 cm-1? A4. A O-H stretch C-H stretch O-H bend C-O stretch А5. How many resonances will appear in the 13C NMR spectrum of cyclopentanone? 3 4 Section A continues on the next page N468 ABCD ABCD ABCD
- Compounds 1 and 2 were prepared, and the difference in their heats of combustion was found to be 17.2 kJ/mol (J. Am. Chem. Soc. 1961, 83, 606-614): H H 1 Shown below are the lowest-energy conformations of compounds 1 and 2. Identify which drawing matches which compound, and identify which compound has the larger heat of combustion. H H H H |||I 2 H 4 H H The first drawing is compound 1, and compound 1 has a larger heat of combustion because it is the less stable compound. O The first drawing is compound 2, and compound 2 has a larger heat of combustion because it is the less stable compound. The first drawing is compound 2, and compound 2 has a larger heat of combustion because it is the more stable compound. The first drawing is compound 1, and compound 1 has a larger heat of combustion because it is the more stable compound.cỌH CH2OH ОН Н На H ÓH In its most stable chair conformation, indicate the orientation of each of the labeled groups in this substituted cyclohexane. Group a: Group b: Group c:One of the isomers of 1,2,3,4,5,6-hexahydroxycyclohexane, called myo-Inositol, acts as a growth factor in both animals and microorganisms. Draw the most stable chair conformation of myo-Inositol (Note: account the wedge and dash projection). Draw the most stable cis-trans stereoisomer of myo-Inositol. OH HO ОН HO "OH ОН