Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 6, Problem 6.19P
Interpretation Introduction
Interpretation:
The anti-conformation of butane as an isolated structure has any stereocenters or not is to be determined. The stereo-centers in the anti-conformation of butane are to be identified if present.
Concept introduction:
A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also called as asymmetric or stereogenic centers. A carbon atom that does not have four nonequivalent atoms or groups attached to it is known as an achiral carbon atom.
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The following are representations of two forms of glucose. The six-membered ring is known to exist in a chair conformation in each form. Draw clear representations of the most stable conformation of each. Are they two different conformations of the same molecule, or are they stereoisomers that cannot be interconverted by rotation about single bonds? Which substituents (if any) occupy axial sites?
Describe the conformations of the following:
E) Gauche conformation of ethane,
(ü) felipsed conformation of ethene,
(iii) Staggered conformation of propane,
(iv) Syn- and anti-conformation of butane.
Determine whether the structures in each set represent the same molecule, cis-trans isomers, or constitutional isomers. If they are the same molecule, determine whether they are in
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(a)
and
(b)
and
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(d)
and
Chapter 6 Solutions
Organic Chemistry
Ch. 6 - Prob. 6.1PCh. 6 - Prob. 6.2PCh. 6 - Prob. 6.3PCh. 6 - Prob. 6.4PCh. 6 - Prob. 6.5PCh. 6 - Prob. 6.6PCh. 6 - Prob. 6.7PCh. 6 - Prob. 6.8PCh. 6 - Prob. 6.9PCh. 6 - Prob. 6.10P
Ch. 6 - Prob. 6.11PCh. 6 - Prob. 6.12PCh. 6 - Prob. 6.13PCh. 6 - Prob. 6.14PCh. 6 - Prob. 6.15PCh. 6 - Prob. 6.16PCh. 6 - Prob. 6.17PCh. 6 - Prob. 6.18PCh. 6 - Prob. 6.19PCh. 6 - Prob. 6.20PCh. 6 - Prob. 6.21PCh. 6 - Prob. 6.22PCh. 6 - Prob. 6.23PCh. 6 - Prob. 6.24PCh. 6 - Prob. 6.25PCh. 6 - Prob. 6.26APCh. 6 - Prob. 6.27APCh. 6 - Prob. 6.28APCh. 6 - Prob. 6.29APCh. 6 - Prob. 6.30APCh. 6 - Prob. 6.31APCh. 6 - Prob. 6.32APCh. 6 - Prob. 6.33APCh. 6 - Prob. 6.34APCh. 6 - Prob. 6.35APCh. 6 - Prob. 6.36APCh. 6 - Prob. 6.37APCh. 6 - Prob. 6.38APCh. 6 - Prob. 6.39APCh. 6 - Prob. 6.40APCh. 6 - Prob. 6.41APCh. 6 - Prob. 6.42APCh. 6 - Prob. 6.43APCh. 6 - Prob. 6.44APCh. 6 - Prob. 6.45APCh. 6 - Prob. 6.46APCh. 6 - Prob. 6.47APCh. 6 - Prob. 6.48APCh. 6 - Prob. 6.49APCh. 6 - Prob. 6.50APCh. 6 - Prob. 6.51APCh. 6 - Prob. 6.52APCh. 6 - Prob. 6.53APCh. 6 - Prob. 6.54AP
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- For the following pair of molecules, (1) Draw out the chair conformation for each molecule, flip the ring if it is possible. (2) Compare both molecules to circle out which one is more stable. (3) Assign the absolute configuration (R/S) on all the chiral center(s), if it applicable. (4) Name the molecule on the left side. VS.arrow_forwardDraw the boat conformation of the structure 2,4-dibromocylohexane. Are there any chiral centers present? If so, label them.arrow_forwarda. b. For the following two pairs of molecules, (1) Draw out the chair conformation for each molecule, flip the ring if it is possible. (2) Compare both molecules to circle out which one is more stable. (3) Identify their relationship as: constitutional isomer, conformational isomer, stereoisomer or identical. (4) Find all the chiral center on each molecule and label them. Br and ZX- and VS. H H H Br H H ∞arrow_forward
- For the 1,2-dichlorocyclohexane stereoisomers, which conformation of the trans stereoisomer has the lower energy, the diaxial or the diequatorial conformer? Which isomer and conformation of the three you built has the lowest energy? E of all the isomers of 1,2-dichlorocyclohexane. Explain the differences in energy, i.e., identify the sources of strain in the conformations you built. Show the sources of strain in a drawing.arrow_forwardcorresponding to the systelmalilC Thumu projection that illustrates the highest energy conformation of n-propane along any C-C bond axis of the same. Again, place your answer in the space provided. Molecular formula Highest energy conformation of n-propane of n-propane OVER >arrow_forwarda) Draw the following compound in topological structure (zig-zag) and name the conformation that is drawn: b) Determine if each of the following molecules is an enantiomer, a diastereoisomer, an isomer in constitution or identical to the molecule in (a) and which is drawn in the box. Solve all parts otherwise I will downvotearrow_forward
- Discuss and compare two possible chair conformations of cis-1,3-dibromocyclohexane compound. Which conformation is more stable? Why? Explain the reason clearly.arrow_forward1. The structure shown below is a dioxane, and it exists in a chair conformation just like cyclohexane. The specific compound is cis-2-methyl-5-tert-butyl-1,3-dioxane. Draw the two chair conformations of this compound. Surprisingly, the conformer with the tert-butyl group in an axial position is preferred. Circle the preferred conformer. In one sentence or less, explain of this observation. C(CH3)3 CH3arrow_forwardBelow is the energy diagram of different conformations of cyclohexane. Assign a structure to each point indicated by the arrow heads (put A, B, C, or D on the horizontal lines).arrow_forward
- (b) Consider the following tetra-substituted cyclohexane: OH Draw the alternative chair conformations of the cyclohexane compound, shown above. List the unfavourable steric interactions for each chair conformation and determine the more stable conformation of the compound. i.arrow_forwardLabel the following pairs as A) distereoisomers, B) enantiomers, C) conformers, or D) the same. b1 c1 d1 e1 a2 b2 c2 The structures above are labeled a1, a2, b1, b2 ...etc. Using these labels, indicate which compounds above would have an optical rotation ofarrow_forward(B) Draw two chair conformations of the following substituted cyclohexane and identify the most stable conformation. Clearly show the axial and equatorial bonds.arrow_forward
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