Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 11.9, Problem 19P
Interpretation Introduction
Interpretation:
In which isomer the E2 elimination occurs faster is interpreted. The more stable chair confirmation is drawn to explain the reaction.
Concept introduction:
If the leaving group and hydrogen are trans diaxial only the E2 elimination occurs in cyclohexane rings. The E2 elimination occurs by Zaitsevs rule.
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Chapter 11 Solutions
Organic Chemistry
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- Ketones react with alcohols to yield products called acetals. Why does the all-cis isomer of 4-tert-butyl-1,3-cyclohexanediol react readily with acetone and an acid catalyst to form an acetal, but other stereoisomers do not react? In formulating your answer, draw the more stable chair conformations of all four stereoisomers and the product acetal for each one.arrow_forwardDraw each of the above molecules in a 3D perspective. Show all six-membered rings as chairs and all acyclic torsions in staggered conformation. If multiple conformations are possible, choose the best one.arrow_forwardAcyclic conjugated dienes may exist in two conformations, as shown below. Based on differences in steric strain, which of the following dienes has the greatest preference for the s-trans conformation? * s-cis s-trans H;C / H;C- CH3 CH3 CH3 H;C- CH3arrow_forward
- H2/Ptarrow_forward2. 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?arrow_forward(a) Draw all stereoisomers formed by monochlorination of the cis and trans isomers of 1,2-dimethylcyclobutane drawn below. (b) How many constitutional isomers are formed in each reaction? (c) Label any pairs of enantiomers formed.arrow_forward
- Identify the most stable conformation of trans-1-methyl-4-bromocyclohexane (5). A B Me (5) Me Br A Br B Me Br C Me Br Me Darrow_forwardStarting from the wedge-and-dash structure below (sighting down the indicated bond), rotate the back carbon to provide the structure in the conformation that will be capable of an E2 elimination. R/S stereochemistry is graded. H H|||| Br H₂C Br H CH₂ Edit Newman Projection CH3 CH3arrow_forwardPlace the conformations of cis-1-isopropyl-4-methylcyclohexane that are drawn below in order of increasing stability (least stable to most stable). A B C D Earrow_forward
- Which structure represents the most stable chair conformation of trans-1-tert-butyl-3-methylcyclohexane? O structure a O structureb O structure c O structure darrow_forwardDraw all of the products, both constitutional isomers and stereoisomers, of the following reactions. a) 4,4-dibromo-1-ethylcyclopentene ---->Br2,H2O b) 3,3-dibromo-1-ethylcyclopentene ----> HBr c) 3,3-dibromo-1,2-dimethylcyclopentene ----> 1. BH3. 2. H2O2, NaOHarrow_forward2. 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: CN 1) NaCN 2) H+ OH 1) NaBH4 2) H3O+ OH Group -H -CN A Value (kcal/mol) Defined as 0 0.2 kcal/mol -OH 1.0 kcal/mol c. For any products that do have the most stable conformation, does our understanding of the mechanism allow for ‘thermodynamic control'? d. If one of the products is not the most stable, can you explain the observed product based on ‘kinetic control'? (Does the most easily formed transition state result in the observed product?) Consider the chair-like conformation of the starting material.arrow_forward
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