Problem 3(D): Build a model of 3-bromo-4-chloro-2-pentanol to match the configuration of the following stereoisomer. Rotate the C-C bonds so that the five-carbon chain is curved away from the viewer. The five-carbon chain in this "eclipsed" model represents the backbone of the Fischer projection you need to draw by orienting the boxed CH, group at the top. Based on your analysis in part B), which conformation of (-)-menthol is most stable - CHAIR 1 or CHAIR 2? Explain your answer. Br H3C H3C CH3 H3C CI OH Assign R/S configuration to each asymmetric center!!! CH3 CH3 Complete this line and Complete this Fischer Projection!!! wedge representation!!! Task 4: Visualizing chair cyclohexanes Problem 4(A): Menthol is a mild analgesic present in cough lozenges and a variety of topical pain medication. Complete the following scheme based on the Newman projection of the chair conformations of (-)-menthol shown below. Observe the Newman projection of (-)-menthol indicated below to construct your model. CHAIR 1 CHAIR 2 H OHH H CH3 H chair-chair interconversion H' H H H START Here Newman projection of the conformation resulting from chair-chair interconversion. (The projected bonds should be C1-C2 and C4-C5 as in CHAIR 1) CHAIR 1 CHAIR 2 chair-chair interconversion chair representation of the Newman projection drawn above chair representation of the conformation resulting from chair- chair interconversion of CHAIR 1 Problem 4(B): For each conformation drawn above - CHAIR 1 and CHAIR 2, list all unfavorable interactions (1,3- diaxial interactions and other gauche interactions) that are expected to raise the energy of the conformation relative to the chair conformation of unsubstituted cyclohexane. CHAIR 1: CHAIR 2: Based on your analysis in part B), which conformation of (-)-menthol is most stable - CHAIR 1 or CHAIR 2? Explain your answer. 230% Problem 4(C): Now draw the line and wedge representations (lines and wedges attached to a regular hexagon) of (- )-menthol and (+)-menthol. Also provide their systematic names by following the rules of IUPAC nomenclature. Do NOT forget to include the configurations of various asymmetric centers. (-)-menthol: (shown on the previous page) (+)-menthol: What is the relationship between (-)-menthol and (+)-menthol? Rationalize your answer in one sentence. 30 AM Mon Jul 1 Stereochemistry Worksheet - Updated Fall 2023 2 15% Done Task 2: Provide the snapshot of your model of (S)-2-chlorobutane below. Task 3: Provide the snapshot of your model of (2R,3R)-2,3-dichlorobutane below observed with the perspective of a Fisher projection. Task 4: Provide the snapshots of your model of (-)-menthol as depicted by: CHAIR 1 (all non-hydrogen substituents axial). CHAIR 2 (chair-chair interconversion of CHAIR 1)