Concept explainers
Interpretation:
The configuration of (+)-2-methyl-1-butanol has to be determined from the given structure of (-)-2-methyl-1-butanol.
Concept introduction:
The pair of Enantiomers has different configurations.
Enantiomers are named by following Cahn-Ingold-Prelog system, in which R or S letter is used to differentiate between enantiomers.
According to Cahn-Ingold-Prelog system,
The group attached to asymmetric center should be ranked based on the
Check the direction of arrow drawn in the direction of decreasing priority. If the arrow points clockwise direction, then the compound has R configuration. If the arrow points counterclockwise direction, then the compound has S configuration. If the group with lowest priority is not bonded by a hatched wedge, then interchange this group (lowest priority) by group bonded to hatched wedge and draw the arrow in priority order but the configuration is assigned as just reverse.
Pair of enantiomers has different optical activity, which means if one will show levorotatory then the other will show dextrorotatory.
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Chapter 4 Solutions
ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL
- Draw and name the seven aldehydes and ketones with the formula C5H10O. Which are chiral?arrow_forwardThe specific rotation, [a]p, for (-)-2-butanol is +14. What is the observed rotation for a solution of 3.3 g of (-)-2-butanol in 10 mL of water in a sample tube having a pathlength of 10 cm? degrees . The observed rotation of a solution of 0.75 g of a compound in 10 mL of water is -6.9 degrees. If the pathlength is 10 cm, what is the specific rotation of the compound?arrow_forwardWhich of these compounds is expected to be optically active at room temperature? ÇOOH H OH CH, CH, Br но- Br CH H- OH COOH CH (A) (B) (C) (D) O B OD O Aarrow_forward
- 5A Explain which of the following statements are true and which are false. i. N,N'-dicyclohexylurea (DCU) is the dehydrating reagent that converts a carboxylic acid to the corresponding anhydride. ii. The fact that carbonyl compounds have a lower boiling point than alcohols with the same C atoms is because the molecular dipole moment of carbonyl compounds is less than that of alcohols. iii. 3-Methylbut-2-en-2-ol is the only tautomeric structure of 3- methylbutan-2-one.arrow_forwardWhich of the following represents the lowest energy conformer of a compound that could be described (inaccurately) as 3-(1-methylethyl)cyclohexanol with a trans- relationship between groups? OH OH но HO (A) (B) (C) (D) O Structure D Structure C Structure A Structure Barrow_forward12. Natural (2)-menthol, the essential oil primarily responsible for the flavor and aroma of peppermint, is the IR,25,5R-stereoisomer. (a) Identify (2)-menthol from the structures you drew for Problem 50, part (b). (b) Another of the naturally occurring diastereomers of menthol is (1)-isomenthol, the 1S 2R5R- stereoisomer. Identify (1)-isomenthol among your structures. (c) A third is (1)-neomenthol, the 15.25,SR-compound. Find (1)-neomenthol among your structures. (d) Based on your understanding of the conformations of substituted cyclohexanes (Section 4-4), what is the stability order (from most stable to least) for the three diastereomers, menthol, isomenthol, and neomenthol?arrow_forward
- The reaction of (R)-1-iodo-2-methylbutane with hydroxide ion forms an alcohol without breaking any bonds to the asymmetric center. The alcohol rotates the plane of polarization of plane-polarized light counterclockwise. What is the configuration of (+)-2-methyl-1-butanol?arrow_forwardΩ Enilconazole CH₂ Enilconazole is an agricultiral fungicide. Synthesis of enilconazole involves an SÃ2 reaction between an alkoxide ion and a secondary alkyl chloride. Draw the structures of these components if the chirality of the resulting ether is (R).arrow_forward(9) How many chiral centers are present in a molecule of 1,3-dimethylcyclohexane? (C) 2 (D) 3 1 (A) O (10) What is the percent composition of a mixture of (S)-(+)-2-butanol, [a] = +13.52°, and (R)-(-)-2-butanol, [a] = -13.52°, with a specific rotation [a]D = -6.76° (A) 75%R 25%S (B) 25%R 75%S (C) 50%R 50%S 67%R 33%Sarrow_forward
- VIII. Assign R, S configurations to each chirality center in the molecule below. Br CH3 X OH CH3 I I (arrow_forward7 For the following compound with two chiral centers assign 'R' and 'S' configurations. Draw enantiomers and diastereomers for the following compound? How many enantiomers and diastereomers are possible. Assign (R) and (S) configurations for all the structures. What are diastereomers? COOH H CI € Br -H CH3arrow_forward(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.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning