Label a curve of potential energy vs. dihedral angle for the Newman conformations of 2,3-dimethylbutane. In each case, the C-2 to C-3 bond rotates in the clockwise direction. Step 1: Translate line-bond notation to the Newman projection. Step 2: Identify Newman projections for each rotation. HI ||| H Step 3: Identify the relative stability of each Newman projection. Step 4: Construct the energy diagram. Step 2: Identify the Newman projections for each rotation (continued). As the back carbon rotates, the Newman projections alternate from staggered to eclipsed and back again. Fill in the remaining conformations for each conformation labeled with the angle of internal rotation from the starting Newman projection. Starting structure - 0° 120° 180° CH3 H₂C H H Answer Bank CH3 -CH3 CH3 H CH3 □ O CH3 O 240° 300° CH3 CH3 DFØ CH3 H CH3 CH3 H CH3

Label a curve of potential energy vs. dihedral angle for the Newman conformations of 2,3-dimethylbutane. In each case, the C-2 to C-3 bond rotates in the clockwise direction. Step 1: Translate line-bond notation to the Newman projection. Step 2: Identify Newman projections for each rotation. HI ||| H Step 3: Identify the relative stability of each Newman projection. Step 4: Construct the energy diagram. Step 2: Identify the Newman projections for each rotation (continued). As the back carbon rotates, the Newman projections alternate from staggered to eclipsed and back again. Fill in the remaining conformations for each conformation labeled with the angle of internal rotation from the starting Newman projection. Starting structure - 0° 120° 180° CH3 H₂C H H Answer Bank CH3 -CH3 CH3 H CH3 □ O CH3 O 240° 300° CH3 CH3 DFØ CH3 H CH3 CH3 H CH3

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter6: Alkanes & Alkenes

Section: Chapter Questions

Problem 4E: Consider the molecule 1-bromo-2-methylbutane. C3 and C4 should be drawn as Et as in theexample. This...

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Label a curve of potential energy vs. dihedral angle for the Newman conformations of 2,3-dimethylbutane. In each case, the C-2 to C-3 bond rotates in the clockwise direction. Step 1: Translate line-bond notation to the Newman projection. Step 2: Identify Newman projections for each rotation. HI!!!! "Η Step 3: Identify the relative stability of each Newman projection. Step 4: Construct the energy diagram. Step 4: Construct the energy diagram. You have determined the different Newman projections and the relative stabilities. Plot a potential energy vs. dihedral angle graph for the Newman conformations of 2,3-dimethylbutane. Return to the previous questions to view the substituents at each angle of bond rotation and the relative stability. Points on the graphing module are graded for location. When you click and hold onto the first dot, highlighted points appear that represent possible positions for the dot. Consider the energy level for each angle of rotation, then drag the dot to the…
Label a curve of potential energy vs. dihedral angle for the Newman conformations of 2,3-dimethylbutane. In each case, the C-2 to C-3 bond rotates in the clockwise direction. Step 1: Translate line-bond notation to the Newman projection. Step 2: Identify Newman projections for each rotation. HI "H Step 3: Identify the relative stability of each Newman projection. Step 4: Construct the energy diagram. The potential energy diagram will look at the energy levels as the carbon-carbon bond rotates. Let's rotate the back carbon 60°. Draw the expected Newman projection. Answer Bank CH3 □ The Newman projection is gauche interactions. eclipsed. staggered. There are 1 2 3 H
Label a curve of potential energy vs. dihedral angle for the Newman conformations of 2,3-dimethylbutane. In each case, the C-2 to C-3 bond rotates in the clockwise direction. Step 1: Translate line-bond notation to the Newman projection. Step 2: Identify Newman projections for each rotation. TH Step 3: Identify the relative stability of each Newman projection. Step 4: Construct the energy diagram. Step 1: Translate line-bond notation to Newman projection. Eye |||||H H The Newman projection is O staggered O eclipsed H Answer Bank CH3
Label a curve of potential energy vs. dihedral angle for the Newman conformations of 2,3-dimethylbutane. In each case, the C-2 to C-3 bond rotates in the clockwise direction. Step 1: Translate line-bond notation to the Newman projection. Step 2: Identify Newman projections for each rotation. !!!H Step 3: Identify the relative stability of each Newman projection. Step 4: Construct the energy diagram. Step 3: Identify the relative stability of each Newman projection (continued) Compare the eclipsed Newman projections and determine the relative stability. 0° 120° 240° CH3 CH3 H H₂C Da -CH3 H H CH3 CH3 H H3C H3C Select the true statement. 0° is the most stable conformation. 120° and 240° are less stable and have equivalent stability. 0° is the most stable, followed by 120°, then 240° 240° is the most stable, followed by 120°, then 0° 120° and 240° are the most stable and have equivalent stability. 0° is the least stable, H3C H -CH3 CH3 H CH3
HI!!!!! 0° H €2H Looking at C1 with C2 behind C1, complete the Newman Projection diagrams. The angles are defined as the dihedral angle between C1-1 and C2-1. 60° H 120° 180° Complete the following potential energy diagram by plotting relative energy of each of the above Newman Projections is versus dihedral angle. The plot should show the correct relative order of the potential energy of each conformation.
8 po Din 3. Consider 1-bromopropane. (looking at C₁ and C₂ bond) I) Draw a Newman projection (conformation) in which methyl and bromine are anti. II) Draw a Newman projection (conformation) in which methyl and bromine are in gauche. III) Draw a Newman projection (conformation) which represents the least stable eclipsed conformation.
b. Draw a Newman projection of the given compound H viewed from C-2 to C-3 orientated according to the first template. Then use the Newman projection to demonstrate the most stable conformation around the C2-C3 bond according to the second template. (Hint: Order of decreasing group size 'Pr > CH2CH3 > CH3 > OH > Br > H] NH2 Me Ме H 'Pr Given conformation Most stable conformation
3. Draw the most stable Newman projection of 1-bromocyclohexane looking down the C-1 to C-2 bond.
Starting from the wedge-and-dash structure below (sighting down the indicated bond), rotate the back carbon to provide the structure in the conformation that will be capable of an E2 elimination. R/S stereochemistry is graded. H H|||| Br H₂C Br H CH₂ Edit Newman Projection CH3 CH3
Question 11 of 22 > O Macmillan Learning Translate the given conformer from the wedge-and-dash drawing into its Newman projection. You might find it helpful to make a model, then manipulate it to the desired viewpoint. H3C H C... Br "|||H CH3 Which Newman structure matches the conformer? CH3 H B H CH3 H $ Br H -CH3 Br -CH3 CI O H CI CI H H CH3 -I Br CH3 Br -CH3 CH3
3. For pentane draw Newman projections for the Syn-periplanar, conformation. the Anti- periplanar conformation and a Gauche conformation. Use C2 as the front carbon and C3 as the back carbon. Label each conformation, circle the highest energy conformation and underline the lowest energy conformation.
5. Draw the Newman Projection of cis-1,2- dimethylcyclopentane looking down the C1-C2 bond. Assume a planar conformation (i.e. the methyl groups would be eclipsed).