3 - Newman and Chairs (Answers - Monday) PDF

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CHM 1321...

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CHM 1321 DGD #3 – Newman Projectionsand Chair Conformation For help going between perspectives: https://molview.org/ Newman Projections

1. Draw a line structure consistent with these Newman projections. You can take on any perspective you want—as long as the bonds stay the same! Cl OH

H H

H

Br

COOH

CH2CH3 OH

HO

NH2

H F

CH3

COOH CH3 COOH

CH3

2. Draw the Newman projection for each of the labelled bonds. Make sure to draw the projection using the given perspective. O HO

Cl

OH

3. Rank the following conformers (same molecule but different conformation due to rotation, flipping, etc.) from highest energy (1) to lowest energy (4). H CH3

CH3 H

H

H

H

CH H 3

H H

H3CCH3

CH3 H

CH3

H

H

H H

H H

H

CH3

4. For the highest energy conformer in question 3, change the methyl groups into tert-butyl groups (C(CH3)3). Do you expect the energy to be higher/lower/the same? Justify your answer?

Chair Conformation

1. Draw a line structure consistent with these chair conformations.

OH NH2 Cl

2. Label the substituents on the chair conformations from question 1 as either axial or equatorial.

3. Draw a chair conformation consistent for the given cyclohexane molecules. Then, check to make sure that the conformation you’ve drawn is the most stable form. OH

COOH NH2

OH O

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4. Glucose is a simple sugar (a monosaccharide) and an important carbohydrate in biology. Cells use it as a source of energy and a metabolic intermediate. Glucose is one of the main products of photosynthesis and starts cellular respiration. Draw the most stable chair conformation for glucose. CH2OH HO

O

HO

OH OH...