ẞ-Eliminations that follow an E2 mechanism have stereochemical implications that need to beaddressed. Elimination MUST occur from a conformation with an "anti periplanar" between theleaving group and ẞ-hydrogen. This corresponds to a staggered conformation in acyclic systems and"trans-diaxial" in cyclohexane chairs.A. Examples of acyclic systemsHCH3EtNaOCH3H3C7EtBrCHOOSBrH CH3PhNaOH13H t-BuHHBrNaOHPhPh H1HOOGM

1. E2 Elimination and Stereochemistry: For an E2 elimination to occur, the leaving group and the…

Answered: ẞ-Eliminations that follow an E2…

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter14: Elimination

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Problem 40CTQ

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2) Draw Newman projections of all staggered conformations of (S)-butan-2-ol. Clearly mark the highest energy conformation. 3) Draw both chair conformations of (1S,3R)-1-chloro-3-isopropylcyclohexane. Clearly mark the most stable conformation, and also the conformation which enables E2 elimination.
Consider compound Q shown below (trimethylcyclohexane isomer). compound Q Which of the following is the most stable conformation of compound Q? I ||| CH3 Select one: O A. II OB. I O C. III O. D. IV H CH3 H CH3 H H- CH3 CH3 H CHS ||| H IV CH3 H CH₁ CH3 fff, H CH3 CH3 CH3
Nn.127. Subject :- Chemistry
The compounds drawn should each contain a cyclohexane ring. For all three compounds draw a wedge and dash structure, Chair I, and Chair II conformations. Formula: C9H18 with substitution 1,1- disubstituted with stereochemistry of (R,S) Formula: C7H13Cl with substitution 1,3- disubstituted with stereochemistry of (R,R) Formula: C7H14O with substitution 1,4- disubstituted with stereochemistry (S,S)
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?
5) relationship between the pairs of structures. NOTE: Each term may be used more than Choose the term from the five terms listed below that BEST describes the once and not all terms need be used. Identical Diastereomers Enantiomers Constitutional isomers Not isomers CH3 CH3 ÇI H3C-Br CH3 Br -CI H,C. D-H H3C- Br H- -D Br CH3 -CI ČH3 OH H3C, CHO OHC, OH OH H. HO CHO OHC CH3 H. OH ÓH
a a a d 0° 60° 120° 180° Complete the following potential energy diagram by plotting relative energy of each of the above Newman Projections is versus dihedral angle. The plot should show the correct relative order of the potential energy of each conformation.
6. Draw the stable conformations of the following molecules. A) (2R,3S)-3-methyl-2-hexanol (staggered Newman Projection). B) meso 1,2-dibromo cyclohexane in (chair conformation) 7. What is the value of the equilibrium constant for the following equilibrium? HC ECH + NaOH HC=C: Na + H₂O pk₂= 25 pka = 15.7
None
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Which of these products is the result of a hydride shift occuring during the substitution reaction of aqueous 2-chloro-3-methylpentane? CH3CH2CCH2CH3 || CH2 CH3CH(OH)CH(CH3)CH2CH3 CH2=CHC(CH3)=CHCH3 CH3CH=C(CH3)CH2CH3 CH3CH2C(CH3)CH2CH3 | OH

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