Name: Page 4 of 7 Task 2: Newman projection and conformational analysis of 2,3-dichlorobutane (From your model kit, Use white pieces for hydrogens and green pieces for chlorines for this task.) Problem 2(A): Build a model of 2,3-dichlorobutane and orient it in a staggered conformation so that the dihedral angle between C1 and C4 is 180° as shown below. Complete the line and wedge template indicated below. In order to draw the Newman projection, orient the model so you are looking down on C2-C3 bond (projected bond). Complete the Newman projection template indicated below. H CH3 CI 2 5 of 7 Name: 'CH3 Ꭰ H3C H 3Cl Hwww CI 4 CH3 4 CH3 CH 2,3-dichlorobutane (staggered) H B CH3 4 CH3 kJ/mol kJ/mol E kJ/mol kJ/mol F Page 5 of 7 kJ/mol kJ/mol Problem 2(B): Orient your model of 2,3-dichlorobutane in an eclipsed conformation so that the dihedral angle between C1 and C4 is 0°. Complete the line and wedge template indicated below. Orient the model so you are looking down on C2-C3 bond (projected bond). Complete the Newman projection template indicated below. CI H Problem 2(D): Draw the quantitative energy profile for 2,3-dichlorobutane by utilizing the relative energy of six conformations you calculated in problem 2C. Be mindful of what the two axes represent in the conformational analysis plot you draw (x axis= dihedral angle between C¹ methyl and C+ methyl, y axis = potential energy). Your conformational analysis plot should represent the relative energy of all possible conformations in the plot below (and not just the six above). USE A RULER - sloppy work deserves no credit!! H 2 3 CI H3C 4 CH3 2,3-dichlorobutane (eclipsed) CH3 CH3 Problem 2(C): This problem is based on conformational analysis of 2,3-dichlorobutane. Observe your model in a manner that C2 is the front carbon and C3 is the back carbon. Complete the Newman projections (A) (F) by rotating the back carbon (C2) by 60° clockwise. You must keep the front carbon stationary. Calculate the relative energy of each conformation by adding up the energy costs for each gauche or eclipsed interaction. Interaction Energy cost Interaction (kJ/mol) Energy cost (kJ/mol) H/H eclipsed 4 CI/CH3 eclipsed CH3/CH3 eclipsed 14 CI/CI eclipsed 12 27 H/CH3 eclipsed 6 CI/H eclipsed 6 CH3/CH3 gauche 4 CI/CH3 gauche 3 CI/CI gauche 5 CI/H gauche ignore CH3/H gauche ignore

Name: Page 4 of 7 Task 2: Newman projection and conformational analysis of 2,3-dichlorobutane (From your model kit, Use white pieces for hydrogens and green pieces for chlorines for this task.) Problem 2(A): Build a model of 2,3-dichlorobutane and orient it in a staggered conformation so that the dihedral angle between C1 and C4 is 180° as shown below. Complete the line and wedge template indicated below. In order to draw the Newman projection, orient the model so you are looking down on C2-C3 bond (projected bond). Complete the Newman projection template indicated below. H CH3 CI 2 5 of 7 Name: 'CH3 Ꭰ H3C H 3Cl Hwww CI 4 CH3 4 CH3 CH 2,3-dichlorobutane (staggered) H B CH3 4 CH3 kJ/mol kJ/mol E kJ/mol kJ/mol F Page 5 of 7 kJ/mol kJ/mol Problem 2(B): Orient your model of 2,3-dichlorobutane in an eclipsed conformation so that the dihedral angle between C1 and C4 is 0°. Complete the line and wedge template indicated below. Orient the model so you are looking down on C2-C3 bond (projected bond). Complete the Newman projection template indicated below. CI H Problem 2(D): Draw the quantitative energy profile for 2,3-dichlorobutane by utilizing the relative energy of six conformations you calculated in problem 2C. Be mindful of what the two axes represent in the conformational analysis plot you draw (x axis= dihedral angle between C¹ methyl and C+ methyl, y axis = potential energy). Your conformational analysis plot should represent the relative energy of all possible conformations in the plot below (and not just the six above). USE A RULER - sloppy work deserves no credit!! H 2 3 CI H3C 4 CH3 2,3-dichlorobutane (eclipsed) CH3 CH3 Problem 2(C): This problem is based on conformational analysis of 2,3-dichlorobutane. Observe your model in a manner that C2 is the front carbon and C3 is the back carbon. Complete the Newman projections (A) (F) by rotating the back carbon (C2) by 60° clockwise. You must keep the front carbon stationary. Calculate the relative energy of each conformation by adding up the energy costs for each gauche or eclipsed interaction. Interaction Energy cost Interaction (kJ/mol) Energy cost (kJ/mol) H/H eclipsed 4 CI/CH3 eclipsed CH3/CH3 eclipsed 14 CI/CI eclipsed 12 27 H/CH3 eclipsed 6 CI/H eclipsed 6 CH3/CH3 gauche 4 CI/CH3 gauche 3 CI/CI gauche 5 CI/H gauche ignore CH3/H gauche ignore

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Transcribed Image Text:Name: Page 4 of 7 Task 2: Newman projection and conformational analysis of 2,3-dichlorobutane (From your model kit, Use white pieces for hydrogens and green pieces for chlorines for this task.) Problem 2(A): Build a model of 2,3-dichlorobutane and orient it in a staggered conformation so that the dihedral angle between C1 and C4 is 180° as shown below. Complete the line and wedge template indicated below. In order to draw the Newman projection, orient the model so you are looking down on C2-C3 bond (projected bond). Complete the Newman projection template indicated below. H CH3 CI 2 5 of 7 Name: 'CH3 Ꭰ H3C H 3Cl Hwww CI 4 CH3 4 CH3 CH 2,3-dichlorobutane (staggered) H B CH3 4 CH3 kJ/mol kJ/mol E kJ/mol kJ/mol F Page 5 of 7 kJ/mol kJ/mol Problem 2(B): Orient your model of 2,3-dichlorobutane in an eclipsed conformation so that the dihedral angle between C1 and C4 is 0°. Complete the line and wedge template indicated below. Orient the model so you are looking down on C2-C3 bond (projected bond). Complete the Newman projection template indicated below. CI H Problem 2(D): Draw the quantitative energy profile for 2,3-dichlorobutane by utilizing the relative energy of six conformations you calculated in problem 2C. Be mindful of what the two axes represent in the conformational analysis plot you draw (x axis= dihedral angle between C¹ methyl and C+ methyl, y axis = potential energy). Your conformational analysis plot should represent the relative energy of all possible conformations in the plot below (and not just the six above). USE A RULER - sloppy work deserves no credit!! H 2 3 CI H3C 4 CH3 2,3-dichlorobutane (eclipsed) CH3 CH3 Problem 2(C): This problem is based on conformational analysis of 2,3-dichlorobutane. Observe your model in a manner that C2 is the front carbon and C3 is the back carbon. Complete the Newman projections (A) (F) by rotating the back carbon (C2) by 60° clockwise. You must keep the front carbon stationary. Calculate the relative energy of each conformation by adding up the energy costs for each gauche or eclipsed interaction. Interaction Energy cost Interaction (kJ/mol) Energy cost (kJ/mol) H/H eclipsed 4 CI/CH3 eclipsed CH3/CH3 eclipsed 14 CI/CI eclipsed 12 27 H/CH3 eclipsed 6 CI/H eclipsed 6 CH3/CH3 gauche 4 CI/CH3 gauche 3 CI/CI gauche 5 CI/H gauche ignore CH3/H gauche ignore

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