Laboratory Techniques in Organic Chemistry
4th Edition
ISBN: 9781464134227
Author: Jerry R. Mohrig, David Alberg, Gretchen Hofmeister, Paul F. Schatz, Christina Noring Hammond
Publisher: W. H. Freeman
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Chapter 8, Problem 4Q
Interpretation Introduction
Interpretation:
When the same computational chemistry method is performed by two different students, the reason for the different values for conformations needs to be explained and the method of determining the lowest energy value in this case needs to be discussed.
Concept Introduction:
Chair-like conformation for cyclohexane molecule is a three-dimensional way of representing the molecule. This is a non-planar conformation with all the angles approximately equal to 109.5o. This is stable conformation because it has lower strain energy than the flat hexagonal shape. All the carbon centers are equivalent in the chair conformation. In the flat hexagonal shape, the wedge and dashed bonds represent the group attached directed away and towards the plane of paper respectively. In the chair conformation, these wedge and dashed bonds are axial and equatorial respectively.
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Why are these two conformational isomers? I was under the impression that in molecules with only sigma bonds, the bonds can rotate freely, and so the placement of the chlorines wouldn't matter?
I need help figuring out which ones are conformation,constitutional isomer, cis isomer and trans isomer.
Draw the structure(s) of all of the possible monochloro derivatives of 2,2-dimethylpropane, C3H11CI.
• You do not have to consider stereochemistry.
• Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right co
Separate structures with + signs from the drop-down menu.
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Laboratory Techniques in Organic Chemistry
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- Make a model of cyclooctane. At least 8 different somewhat stable conformations of this molecule can exist. Draw some of the conformations you can find. Can you find a conformation of this ring that is strain-free? Identify the type of strain present in all possible conformations of this molecule.arrow_forwardStereoisomers share the same connectivity and differ only in the way their atoms are arranged in space. Draw the structure of a compound that is a stereoisomer of cis-1,4-dibromocyclohexane.(Note that the question asks for a different stereoisomer of the named compound and not the named compound itself.)Use the wedge/hash bond tools to indicate stereochemistry where it exists.In cases where there is more than one answer, just draw one.arrow_forwarda graph representing the potential energy of different conformational states of 2-methylbutane is shown below. identify the point on the graph for the following conformation.arrow_forward
- Draw the cis isomer of the structure shown below. D • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • In cases where there is more than one answer, just draw one. If the structure does not have cis/trans isomers, simply redraw the molecule without stereobonds.arrow_forwardIn this molecule’s other chair conformation, how many (non H) axial positions are there?arrow_forwardThere are several aromatic compounds with the formula CgH9Cl. Draw those that have a disubstituted ring where the chlorine is attached to the ring. • You do not have to consider stereochemistry. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu.arrow_forward
- Consider 2-methylbutane (isopentane). Sighting along the C2-C3 bond, Draw a Newman projection formula for the most stable conformation. Based on your drawing, determine the total strain energy for this conformation. Given the following strain energies with respect to atoms/groups bonded to C-C (one atom/group bonded to each C) H H eclipsed: 4 kJ/mol CH3 H eclipsed: 6 kJ/mol CH3 CH3 eclipsed: 11 kJ/mol CH3 CH3 gauche staggered: 3.8 kJ/mol Select one: O A. 11 kJ/mol O B. 7.6 kJ/mol O C. 3.8 kJ/mol O D. 14.8 kJ/molarrow_forwardaccording to the figure which molecule has the greatest energy savings for its comjugated system?arrow_forwardConsider the following four molecules, count how many sp2 atoms are conjugated how many are non-conjugated. Molecule A has _ conjugated sp2 atoms and _ non-conjugated sp2 atoms. Molecule B has _ conjugated sp2 atoms and _ non-conjugated sp2 atoms. Molecule C has _ conjugated sp2 atoms and _ non-conjugated sp2 atoms. Molecule D has _ conjugated sp2 atoms and _ non-conjugated sp2 atoms.arrow_forward
- a) Draw all Newman projections of your molecule's conformations in which the CH3 group and the H of the CHY2 group are positioned 'ANTI' to each other. Be sure to put in the correct X and Y atoms, bonded to the correct C atoms, for your molecule. X = FY=I Conformations = 60 deg and - 180 deg 60 deg dihedral angle = - 179.987 deg 180 deg · - dihedral angle = 179.814 degarrow_forwardWhich of the following statements about the HOMO and LUMO of conjugated molecules is correct? The energy gap between the HOMO and LUMO in conjugated molecules is greater than in unconjugated molecules. resulting in the brilliant colors in the visible wavelength range. When a conjugated molecule absorbs light, an electron transitions from the LUMO to the HOMO. O The energy gap belween the HOMO and LUMO in conjugated molecules is smaller than in unconjugated molecules. O None of these statements are correct. 1ptsarrow_forwardSquare planar molecules with formula AB2C2 and octahedral molecules with formulas AB4C2 and AB3C3 feature diastereoisomers. Recall that trigonal bipyramidal geometry features two distinct positions: axial and equatorial. Draw all diastereoisomers for trigonal bipyramidal molecules with formula (a) AB4C and (b) AB3C2. You must indicate the stereochemistry using full and dashed wedges and label all positions as either axial (ax) and equatorial (eq)..arrow_forward
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