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Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Question
Chapter 6, Problem 8CTQ
(a)
Interpretation Introduction
Interpretation:
The location of C2, C3, and C4of butane in model 4 that is Newman projection should be predicted.
Concept Introduction:
The spatial arrangement of atoms in a molecule obtained by rotation around carbon - carbon single bond is known as conformation.
(b)
Interpretation Introduction
Interpretation: Whether each member of the group sight down the C2-C3 bond of the model or not needs to be determined.
Concept Introduction:
The spatial arrangement of atoms in a molecule obtained by rotation around carbon - carbon single bond is known as conformation.
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Students have asked these similar questions
1. Draw the most and least stable Newman projections for the following molecules (focus
on C2 and C3).
a. 2-chloro-2-fluoropentane
b. 2,2-dimethylbutane
c. 2-chloro-2-methylpentane
d. 1,2-dibromoethane
Consider 1– Bromo – 2– methylbutane.
A. Looking down at the C1:C2 bond draw the Newman projection with the lowest energy
B. looking down at the C1:C2 bond draw the Newman projection highest energy
5. Chairs and E2
b.
a. Draw the line-bond structure of (1R, 2S,3S)-1-ethyl-2-iodo-3-isopropylcyclohexane.
Draw both chair flips of (1R, 2S,3S)-1-ethyl-2-iodo-3-isopropylcyclohexane. Showing all
calculations, determine which is the more stable conformation.
C. Which chair flip is able to undergo E2 elimination? Justify your answer.
d. Show the product of such an E2 elimination using NaOEt as base.
Chapter 6 Solutions
Organic Chemistry: A Guided Inquiry
Ch. 6 - Prob. 1CTQCh. 6 - Prob. 2CTQCh. 6 - Prob. 4CTQCh. 6 - Prob. 5CTQCh. 6 - Complete this graph of relative potential energy...Ch. 6 - Prob. 7CTQCh. 6 - Prob. 8CTQCh. 6 - Prob. 9CTQCh. 6 - Consider the Newman projection below. a. Draw a...Ch. 6 - Draw a Newman projection showing the lowest P.E....
Ch. 6 - Prob. 12CTQCh. 6 - Prob. 13CTQCh. 6 - In skeletal representations the hydrogens are not...Ch. 6 - Prob. 15CTQCh. 6 - Prob. 16CTQCh. 6 - Prob. 17CTQCh. 6 - Prob. 19CTQCh. 6 - Prob. 20CTQCh. 6 - Prob. 21CTQCh. 6 - Prob. 22CTQCh. 6 - Prob. 23CTQCh. 6 - Draw a constitutional isomer of pentane,...Ch. 6 - How many H’s are lost from the molecular formula...Ch. 6 - How many ifs are lost from the molecular formula...Ch. 6 - Prob. 27CTQCh. 6 - What is the degree of unsaturation for the example...Ch. 6 - Without counting hydrogens, determine which one of...Ch. 6 - Determine the degree of unsaturation (and draw a...Ch. 6 - a model of each molecule shown above: Is the...Ch. 6 - Prob. 32CTQCh. 6 - Prob. 33CTQCh. 6 - Label each double bond E, Z, or neither. (It may...Ch. 6 - Prob. 35CTQCh. 6 - Prob. 36CTQCh. 6 - Indicate the relationship between each pair....Ch. 6 - Prob. 38CTQCh. 6 - Prob. 1ECh. 6 - Prob. 2ECh. 6 - Using your model of butane (CH3CH2CH2CH3) ,...Ch. 6 - Consider the molecule 1-bromo-2-methylbutane. C3...Ch. 6 - Prob. 5ECh. 6 - Prob. 8ECh. 6 - Prob. 9ECh. 6 - Prob. 10ECh. 6 - Prob. 11ECh. 6 - Prob. 12ECh. 6 - Prob. 13ECh. 6 - Prob. 15ECh. 6 - Prob. 16ECh. 6 - Prob. 17ECh. 6 - Prob. 18ECh. 6 - Prob. 19ECh. 6 - Prob. 20ECh. 6 - Prob. 21ECh. 6 - Double bonds do not rotate freely under normal...Ch. 6 - up an example (not appearing in this ChemActivity)...Ch. 6 - Prob. 24ECh. 6 - Prob. 25E
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- i need the answer quicklyarrow_forwardDraw the most and least stable Newman projections for the following molecules ( focus on C2 and C3). a. 2-chloro-2- fluoropentane b. 2,2-dimethylbutane C. 2-chloro-2-methylpentane d. 1,2-dibromoethanearrow_forwardWhat is an acceptable Newman projection for the molecule shown below, looking down the indicated bond? O A. O B. H. Harrow_forward
- Draw 1,2,3,4,5,6-hexachlorocyclohexane with a. all the chloro groups in axial positions. b. all the chloro groups in equatorial positions.arrow_forward2. In aqueous solution d-glucose (or dextrose) exists in equilibrium between a linear and cyclic form shown below. A. Mark all the stereocenters in the linear form of the molecule. Number them 1,2,3, etc. B. Draw out the reaction that converts the linear form to the 6-membered ring using the arrow formalism. C. Identify the stereocenters in the 6-member ring that correspond to the stereocenters in the linear form marking them as 1,2,3, etc. The reaction also created a new stereocenter. Mark it as H -OH HO--H H--OH нон Ho но HO HO H он H-OH H но.arrow_forward. Consider the hash/wedge structure below. a. Draw the Newman projection of the bond indicated, keeping the conformation the same. НО b. Draw the Newman projection for the most stable conformation CI c. In the Newman projection for part b, label all gauche interactions.arrow_forward
- A. Circle the following molecules that have the S configuration. CH,CH3 CH,CH3 H. H3C-- H. CH=CH2 CH(CH3)2 CH3 CH3CH, CH2 HO, 3 1arrow_forwardSight along the C2-Cl bond of 2-methylpropane (isobutane). a. Draw a Newman projection of the most stable conformation. b. Draw a Newman projection of the least stable conformation. c. Make a graph of energy versus angle of rotation around the C2-Cl bond. d. Assign relative values to the maxima and minima in your graph, given that an H↔H eclipsing interaction costs 0 kJ/mol and an H↔CH3 eclipsing interaction costs 6.0 kJ/mol.arrow_forward3. Chair conformation time! Consider the following molecule: Ph. iPr NH₂ a. Circle the largest substituent. b. Now take this largest substituent and place it equatorial on one of the cyclohexane rings drawn below. It does not matter which ring you pick first. c. Now move clockwise (or counterclockwise if you're rebellious) around the chair conformation you chose, drawing in the rest of the substituents (including hydrogens). i. Remember, wedges and dashes only indicate up or down here, not axial or equatorial. You can be axial up, equatorial up, axial down, or equatorial down. d. Now look at the chair conformation you left blank. Draw the largest substituent axial on this ring. e. Repeat c, moving along the rest of the chair conformation to draw in the rest of the substituents, including hydrogens. f. Label the most stable conformation: it should be the conformation with the most and/or largest substituents equatorial. #4arrow_forward
- barrow_forwardpt. 4: Molecular Models: Stereoisomers me: 4. Using the model of 2-bromobutane representing the R enantiomer from 4., switch any two groups on the chiral carbon. Compare this to your S enantiomer from 4. a. Are they the same or different? b. Are they the same or enantiomers? C. Now switch any pair of groups around the chiral carbon of the "switched" model again! Compare the "double-switched" model with the other unmodified S molecule from 4. Are they enantiomers or are they identical? С. Shown below is the Fisher projection of (R)-2-bromo-(S)-3-chlorobutane. ne mirror image of this stereoisomer and assign the RIS configurations of iral carbons for both isomers. е ll erarrow_forwardConsider the cyclohexane framework in a chair conformation, where carbon 1 has two substituents, X and Y. a. Label each position as axial or equatorial. b. On the same figure, label all positions that are gauche to the Y group on carbon 1. A bin may hold more than one label. axial equatorial X 1 equatorial equatorial 2 axial axial axial gauche 3 axial gauche 5 equatorial equatorial 4 axial equatorial Answer Bank equatorial gauche axialarrow_forward
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