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, Problem 63P
Interpretation Introduction
Interpretation: The structure of cis-1,2-dimethylcyclohexane needs to be drawn and its stability needs to be explained.
Concept Introduction: A compound is stable when its methyl group present in its equatorial position.
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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.
Construct a model in which a tetrahedral carbon atom has four different colored model atoms attached to it- red, green, orange and white representing 4 different atoms attached to the central atom.
a) Does the atom have a plane of symmetry? why or why not?
b) Now replace the green atom in your model with a second orange atom. Now two of the groups attached to the carbon atom are identical. Does the model now have a plane of symmetry? Describe it.
c)A carbon atom has four different groups attached to the stereogenic center. Draw structural formulas for the following compound and mark stereogenic centers with as asterisk: 1-bromobutane, 2-bromobutane, 1,2-dibromobutane, 1,4-dibromobutane, 2,3-dibromobutane.
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
|
F
OH
C
H
OH
E
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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- For the the structure shown below, Part A) Draw the Newman projections and 3-D sawhorse structures corresponding to the lowest and highest energy conformations for rotation around the C2-C3 bond. Draw the Newman projections looking FROM THE C2 CARBON TO THE C3 CARBON (i.e. with the C2 carbon in the "front"). Part B) Determine the energy difference between the lowest and highest conformations, and be sure to clearly show each energy contribution that you are including in your calculation. 2,3-dimethylpentane ECLIPSING Interactions AB Energy kcal/mol H/H 1.0 H / Me 1.4 H/Et 1.5 H/i-Pr 1.6 H/t-Bu 3.0 Me / Me 2.6 Me / Et 2.7 Me/i-Pr 3.0 GAUCHE A. Interactions Me / Me Me / Et Me / i-Pr Me / t-Bu Et / Et Et / -Pr Et/t-Bu i-Pr/i-Pr B Energy kcal/mol 0.9 0.95 1.1 2.7 1.1 1.6 3.0 2.0arrow_forwardF) Circle the letter corresponding to the relationship of each pair of structures: Identical (1), Conformers (C), Enantiomers (E) (enantiomers can have different conformations). FIRST... determine the absolute configuration of chiral centers. I OH с OH Earrow_forwardc) Draw the most stable chair conformation for each of the following cyclohexanes. Now, "flip" the ring and redraw the molecule in the higher energy form. i) chlorocyclohexane ii) cis-1-chloro-2-methylcyclohexane iii) trans-1-methyl-3-propylcyclohexanearrow_forward
- Label 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_forward3)- Determine the total number of conformers and draw the Chair Structures of the conformers for the Tri-substituted cyclohexane structure given below (i.e., "A"). Draw the relative energy diagram for the possible conformers for the cyclohexane structure below. Note, draw only the required structures for the conformers of A. Also, include hydrogen atoms wherever there are substituents on all of your chair conformers. Answer (Total #of Conformers): Chair Structures: Relative Energy Diagram 8 bas roll 3arrow_forwardQuestion: 2. For the molecule shown below, draw the indicated stereoisomers in the boxes. a) Draw a meso stereoisomer HO c) Circle the chiral centers in the original molecule a) 3. For each of the following individual molecules check all the descriptions that apply. a) b) OH c) HO d) OH Molecule 5 is achiral has an enantiomer has at least one chiral diastereomer contains at least one R chiral center has a meso diastereomer OH OH Br "Br OH ZOH Ph Ph ☆ H₂N NH₂ OH H₂N 4. For each of the pairs of molecules drawn below, place letters in the corner boxes corresponding to all accurate descriptions of the relationship between the two molecules. OH ado H₂N OH Ph H b) Br H Ph Br OH Molecule 6 is achiral has an enantiomer has at least one chiral diastereomer contains at least one R chiral center has a meso diastereomer all letters that apply all letters that apply b) Draw a chiral stereoisomer all letters that apply all letters that apply c) Ph Molecule 7 is achiral has an enantiomer has at least…arrow_forward
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