Consider the structure that results from the ring inversion of the chair conformation below. Add the substituents required to the giv ring to show this structure. Be sure to use guide points when adding substituents.

Consider the structure that results from the ring inversion of the chair conformation below. Add the substituents required to the giv ring to show this structure. Be sure to use guide points when adding substituents.

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter6: Alkanes & Alkenes

Section: Chapter Questions

Problem 4E: Consider the molecule 1-bromo-2-methylbutane. C3 and C4 should be drawn as Et as in theexample. This...

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Concept explainers

Alkanes and Cycloalkanes

Alkanes are saturated organic compounds which are made up of C and H atoms. Alkanes have the general formula of CnH2n+2. Alkane contains sp3 hybridized carbon atoms with four sigmas (σ) bonds & every hydrogen atom is connected with one of the carbon atoms. The size of the alkane could be determined by the number of carbon atoms located in it.

Question

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Consider the structure that results from the ring inversion of the chair conformation below. Add the substituents required to the given cyclohexane
ring to show this structure. Be sure to use guide points when adding substituents.
CI
OH

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2. Our knowledge of chair conformations allows us to use them to determine a great deal about a reaction's mechanism. In particular, using a t-butyl group to 'fix' a cyclohexane in a single conformation can help us learn about the spatial requirements and energetics of a reaction. Consider the following two reaction products: a. NO NID ALOH 1) NaCN 2) H+ 1) NaBH4 2) H3O+ OH Group -H -CN -OH A Value (kcal/mol) Defined as 0 0.2 kcal/mol 1.0 kcal/mol Draw the most stable chair conformation for each of the two products. b. Based on the A values in the table above, do the two products have the most stable conformation at the new stereocenter?
Which compounds have torsional strain (also known as eclipsing strain) in their most stable conformation? Note that compound that has two rings has been drawn in its most stable conformation. Select more than one answer. Even the correct answer gets feedback on this one. Me Me Me Me Me Me D E A. Cyclohexane is a chair, which has only secondary carbons. Since cyclopropane is flat all of the adjacent C's are eclipsed, this giving rise to torsional strain. Since cyclopropane is flat all of the adjacent C's are eclipsed, this giving rise to torsional strain. DE
Consider the structure that results from the ring inversion of the chair conformation below. Add the substituent required to the given cyclohexane ring to show this structure. Be sure to use guide points when adding substituents. H₂C. 0 to 0:0 3 ←
4. Ring Inversion of Substituted Cyclohexane 4.1 Two Chair Conformations of Substituted Cyclohexane Rings boat conformation is 30 hair conformation. Thus, the equilibrium favors the chair conformations. _kJ/mol higher ● ● When Ring Flipping Occurs If a substituent is initially in the axial position, after ring flipping it will be in the position (and vice-versa). equatorial 4 5 5 Connectivity does NOT change. Substituents stay on the same side of the ring that they started on! The cis-trans relationships do NOT change (cis groups stay cis and trans groups stay trans.) H3C Pown 6 3 3 6 CH3 1 CH3 2 1 2 eq I I CH3 H 180N -I 6 in energy than the down ax CH₂ On up on C 1
1. Please first draw a Newman projection representing correct staggered conformation (projection through the green bond). 2. Then identify the eclipsed least stable conformation for the following compound: H₂C. H₂C H- H A Et CH3 Me Et Me Me H Me H B CH3 CH3 Me H Et CH3 Et Me H₂C. H H- H C CH3 Et H CH3 Me Et Me Me H₂C H Me H D CH3 Et Me H CH3 Me Et
Following is a staggered conformation for one of the enantiomers of 2-bromobutane, and several purported Newman projections for this conformation. H H H3C Br H CH3 2-bromobutane H H (a) Is this (R)-2-bromobutane or (S)-2-bromobutane? CH3 CH3 Br H H H CH3 Br b CH3 H Br H CH3 CH3 H (b) Which of the following Newman projections is equivalent to the wedge-dash structure when viewed along the horizontal axis?
O Macmillan Learning Draw every stereoisomer for 1,2-difluoro-1,2-dimethylcyclopentane. Use wedge-and-dash bonds for the substituent groups, and be sure that they are drawn on the outside of the ring, adjacent to each other. Clearly show stereochemistry by drawing the wedge-and-dashed bonds like the example. You should replace the X with the appropriate halide. ZAO X IIX Select Draw all the stereoisomers of 1,2-difluoro-1,2-dimethylcyclopentane. X / || | / Draw 7 C H Rings F LL MacBook Pro More 剛戰戰時易感嗎! Erase
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Trans-1-bromo-2-methylcyclohexane will yield a non-Zaitsev elimination product (3-methylcyclohexene) upon reaction with KOH. Show this reaction by drawing the chair conformations of the reactant and product. Include the curved arrows and explain why the product is not a non-Zaitsev product.
3. 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. #4