13. Newman Projections Draw the Newman projection for the most stable conformation and the least stable conformation for the following molecules. I want you to look down the bond that is in bold (with the front carbon being the one on the left. i) (H3C)2HC-CH3 ii) (H3C)₂HC-CH₂CH3 iii) H3CH₂C-CH₂OH

13. Newman Projections Draw the Newman projection for the most stable conformation and the least stable conformation for the following molecules. I want you to look down the bond that is in bold (with the front carbon being the one on the left. i) (H3C)2HC-CH3 ii) (H3C)₂HC-CH₂CH3 iii) H3CH₂C-CH₂OH

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter6: Alkanes & Alkenes

Section: Chapter Questions

Problem 10CTQ: Consider the Newman projection below. a. Draw a full Lewis structure of this molecule with...

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Following is a chair conformation of cyclohexane with the carbon atoms numbered 1 through 6. (a) Draw hydrogen atoms that are above the plane of the ring on carbons 1 and 2 and below the plane of the ring on carbon 4. (b) Which of these hydrogens are equatorial? Which are axial? (c) Draw the alternative chair conformation. Which hydrogens are equatorial? Which are axial? Which are above the plane of the ring? Which are below it?
A trisubstituted cyclohexane with three substituents-red, green, and blue-undergoes a ring-flip to its alternate chair conformation. Identify each substituent as axial or equatorial, and show the positions occupied by the three substituents in the ring-flipped form.
a model of cyclohexane in a chair conformation, and explain why the names “axial” and“equatorial’ are appropriate.
Consider the Newman projection below. a. Draw a full Lewis structure of this molecule with R1=Me,R2=Et , and R3=iPr . b. Given the sizes of these R groups (R3R2R1) , does the Newman projection above show thelowest potential energy conformation of this bond? If not, draw a Newman projectionshowing the lowest P.E. conformation (sighting down this same bond). c. To draw a Newman projection in the lowest P.E. conformation, the following rule of thumbusually applies: Place the largest group on the front carbon anti to the largest group on theback carbon. Is your answer to the previous question consistent with this rule of thumb?
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.
The diaxial conformation of cis-1, 3-dimethylcyclohexane is approximately 23 kJ/mol (5.4 kcal/mol) less stable than the diequatorial conformation. Draw the two possible chair conformations, and suggest a reason for the large energy difference.
Build a model of methylcyclohexane, and use the model to complete the following Newmanprojections of methylcyclohexane in the chair conformation: a. When the methyl group is in an axial or equatorial (circle one) position, the molecule is inits lowest potential energy conformation. b. Label one Newman projection above anti and the other gauche to describe the relationshipbetween the methyl group and C3 of the ring. c. In general, which is a lower PE conformation, anti or gauche? d. Explain how your answer to b and c provide an explanation for why it is more favorable fora large group to be in an equatorial than an axial position.
4. Draw the most stable conformation for each of the following substituted cyclohexanes; then, in each case, flip the ring and redraw the molecular in the higher energy chair conformation. Shown all conformation in Newman projections. Fill in hydrogens to indicate unsubstituted carbons. a) b) most stable conformation: # higher energy conformation: most stable conformation: higher energy conformation: 00 Do po
2) Label the least favorable conformation and most favorable conformation of the substituted cyclohexane below. Explain your choices in 1-2 sentences or less. H3C H3C H3C F OH CH3 CH3 H3C CH3 F CH3 OH H3C CH3 H3C снаанз F CH3 CH3 -OH
4. Draw the most stable conformation for each of the following substituted cyclohexanes; then, in each case, flip the ring and redraw the molecular in the higher energy chair conformation. Shown all conformation in Newman projections. Fill in hydrogens to indicate unsubstituted carbons. a) b) most stable conformation: higher energy conformation: á most stable conformation: higher energy conformation: 3 Da
translate the bond-line notation structure to the Newman projection by filling int the missing groups (A, B, C, D or E) on the lines in the Newman projection so they match the conformation given in the original structure. Circle if the conformation is a staggered or eclipsed.
We consider the following molecule A: And. THIS Of the following Newman projections, indicate: MeEt F F Me 1 Br 5 Br F And Me THIS CH2CH3 AT CH2CH3 "CH3 Br Br Me Me. THIS 2 Br 6 And And .And And Br CI Me F And 3 F And 7 Me the one that corresponds to the least stable conformation of molecule A: And Br And the one that corresponds to the most stable eclipsed conformation of molecule A: CI Me THIS And Br And Br F F And Me And Choose... Choose... the one that corresponds to molecule A as seen by the eye of the observer in the statement: Choose... the one that corresponds to the least stable staggered conformation of molecule A: the one that corresponds to the most stable conformation of molecule A: Choose... Choose... ◆