Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Chapter 5.6, Problem 5.23E
Interpretation Introduction
Interpretation:Conformation is to be drawn for the given meso compounds in given exercise that contains the mirror plane.
Concept introduction:Meso compounds are those compounds with two chiral centers and there is similar set of four groups at both chiral centers. These chiral centers are arranged in a way that they are superimposable mirror images of each other.
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Students have asked these similar questions
Draw all the conformers of the molecule on the right as Newman
projections sighted along the C3– C4 bond. Label the interactions present
in each conformer. Rank the conformers from lowest to highest energy
(some may be equal).
Compare the following conformers of 1-fluoropropan-1-ol. Match each conformer to
their corresponding relative energy. Recall, the more stable the conformer the lower
the energy.
OH
CH3
'F
2.
HOH
2nd Highest Energy
H
2nd Lowest Energy
H3C
3.
H.
ОН
Lowest Energy
H
'F
Highest Energy
ČH3
4.
H3C,
OH
'F
1.
>
Compare the two possible chair conformations of this molecule. Given
the AG for the two possible chair conformations, calculate the
equilibrium constant for the interconversion between the two chair
conformers at room temperature.
CI
H3C
AG = 1.3 kcal/mol
%3D
AG = -RT In K
%3D
rearranges to
K = e-AG/RT
%3D
R = 1.987 x 10-3 kcal/molK
||
Chapter 5 Solutions
Organic Chemistry: Structure and Function
Ch. 5.1 - Prob. 5.3ECh. 5.1 - Prob. 5.4ECh. 5.1 - Prob. 5.5ECh. 5.2 - Prob. 5.6ECh. 5.2 - Prob. 5.8TIYCh. 5.3 - Prob. 5.9ECh. 5.3 - Prob. 5.11TIYCh. 5.3 - Prob. 5.12ECh. 5.4 - Prob. 5.13ECh. 5.4 - Prob. 5.14E
Ch. 5.4 - Prob. 5.16TIYCh. 5.4 - Prob. 5.17ECh. 5.5 - Prob. 5.18ECh. 5.5 - Prob. 5.19ECh. 5.5 - Prob. 5.20ECh. 5.6 - Prob. 5.21ECh. 5.6 - Prob. 5.22ECh. 5.6 - Prob. 5.23ECh. 5.7 - Prob. 5.24ECh. 5.7 - Prob. 5.26TIYCh. 5.7 - Prob. 5.27ECh. 5 - Prob. 5.1ECh. 5 - Prob. 5.2ECh. 5 - Prob. 30PCh. 5 - Prob. 31PCh. 5 - Prob. 32PCh. 5 - Prob. 33PCh. 5 - Prob. 34PCh. 5 - Prob. 35PCh. 5 - Prob. 36PCh. 5 - Prob. 37PCh. 5 - Prob. 38PCh. 5 - Prob. 39PCh. 5 - Prob. 40PCh. 5 - Prob. 41PCh. 5 - Prob. 42PCh. 5 - Prob. 43PCh. 5 - Prob. 44PCh. 5 - Prob. 45PCh. 5 - Prob. 46PCh. 5 - Prob. 47PCh. 5 - Prob. 48PCh. 5 - Prob. 49PCh. 5 - Prob. 50PCh. 5 - Prob. 51PCh. 5 - Prob. 52PCh. 5 - Prob. 53PCh. 5 - Prob. 54PCh. 5 - Prob. 55PCh. 5 - Prob. 56PCh. 5 - Prob. 57PCh. 5 - Prob. 58PCh. 5 - Prob. 59PCh. 5 - Prob. 60PCh. 5 - Prob. 61PCh. 5 - Prob. 62PCh. 5 - Prob. 63PCh. 5 - Prob. 64PCh. 5 - Prob. 65PCh. 5 - Prob. 66PCh. 5 - Prob. 67PCh. 5 - Prob. 68PCh. 5 - Prob. 69PCh. 5 - Prob. 70PCh. 5 - Prob. 71P
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- F) Circle the letter corresponding to the relationship of each pair of structures: Identical (I), Conformers (C), Enantiomers (E) (enantiomers can have different conformations). FIRST... determine the absolute configuration of chiral centers. H. ІН' I H | H с H Me E Mearrow_forwardBuild a model (attach a photo) for any of the following compounds. What is their relationship: (i) Identical in the same conformation, (ii) conformers, (iii) enantiomers, (iv) diastereomers, (v) constitutional (structural) isomers or none of (i) – (v)? H OH H. HO $Bu CI $Bu Relationship:arrow_forwardUsing Newman projections, draw all of the staggered and eclipsed conformations that result from the rotation around the indicated bond. Look down what is labeled as the C2- C3. Draw a rotational energy profile for this rotation and calculate the strain energy for the least stable and most stable conformations. Using these values, what is the barrier to rotation around the indicated bond?arrow_forward
- Which molecule would have their 2 chair conformations be of equal energies?arrow_forward4. Clearly draw both Chair Conformations. of the following molecule Xordin 5. for the Molecule in Question 4 - Circle the lowest energy Chair Conformat. TAM!arrow_forwardDraw the most stable AND most unstable conformations of the following molecules. Briefly explain your answer. Note, for linear structures looking at rotation around the bond depicted in red. HO OH HN Brarrow_forward
- Please fill in the Newman projections for both chair conformations of the molecule indicated below from the perspective shown. Please indicate which conformations would be lower in energy. CH3, Pr Eye Meo CH3arrow_forwardStereoisomers are isomers that differ in spatial arrangement of atoms, rather than connectivity of atoms. Stereoisomers have different properties, especially in biological systems. Which is the stereochemical relationship between this pair of molecules? OH "OH 8p OH OH ...||| 4 A) enantiomers B) diastereomers C) identical compounds D) constitutional isomers E) Not isomersarrow_forward3) Draw the most stable conformation of (2Z, 4E)-2,4-hexadiene.arrow_forward
- req Zreq 2req 2req 2req [Review Topics) [References] Cyclohexane derivatives exist primarily in the most stable of the available chair conformations. Give the position, axial or equatorial, of each of the three groups shown when the ring is in the most stable chair conformation. If a group divides its time equally between axial and equatorial positions, indicate this with ax/eq. The table of "Axial Strain Energies for Monosubstituted Cyclohexanes" found in the "Strain Energy Increments" section of the Reference tool is useful for answering this question. OH HC Group a is Group bis Group cis Submit Answer OH b Retry Entire Group 9 more group attempts remaining o O · 9020 0arrow_forwardDo a conformational analysis for the following molecules (include energy diagram). H₂C- Hillm Br → H will H H F Br ull Brarrow_forwardWhat is the potential energy of a conformation?arrow_forward
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