Draw the most stable chairconformation of each of the followingcompounds. (a) cis-1,1,4-trimethylcyclohexane (B) trans-1,1,3-trimethylcyclohexane (c) cis-1 fluro-4-ethylcyclohexane-

Step 1: Step 2: Step 3: Step 4:

Answered: Draw the most stable chair conformation…

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter7: Cycloalkanes

Section: Chapter Questions

Problem 12CTQ: Fill in the blanks: cis-1,3-Dimethylcyclohexane has two different chair conformations: one withboth...

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(A)Menthol, used to flavor various foods and tobacco, is the most stable stereoisomer of 2-isopropyl-5-methylcyclohexanol. Draw its most stable conformation. Is the hydroxyl group cis or trans to the isopropyl group? To the methyl group? (b) Neomenthol is a stereoisomer of menthol. That is, it has the same constitution but differs in the arrangement of its atoms in space. Neomenthol is the second most stable stereoisomer of 2-isopropyl-5methylcyclohexanol; it is less stable than menthol but more stable than any other stereoisomer. Write the structure of neomenthol in its most stable conformation.
1.Draw both cis- and trans-1,4-dimethylcyclohexane in their conformations. (a) How many stereoisomérs are there of cis-1,4-dimethylcyclohexane, and how many of rans-1,4-dimethylcyclohexane? (b) Are of the structures chiral? (c) What are the stereochemicar relationships among the various stereoisomers of 1,4-dimethylcyclohexane?
Answer ALL parts. (a) Draw BOTH chair conformations of trans-1,2-dichlorocyclohexane, and explain which is more stable. (b) Draw Newman projections for both the highest and lowest energy conformations of the product obtained from the reaction of (E)-but-2-ene with bromine in water.
Dehydration of 1,2,2-trimethylcyclohexanol with H2SO4 affords 1-tertbutylcyclopentene as a minor product. (a) Draw a stepwise mechanism that shows how this alkene is formed. (b) Draw other alkenes formed in this dehydration. At least one must contain a five-membered ring.
Fill in the blanks: cis-1,3-Dimethylcyclohexane has two different chair conformations: one withboth methyl groups in __________ positions and one with both methyl groups in ____________ positions.
Build a model of methylcyclohexane, and use the model to complete the following Newmanprojections of methylcyclohexane in the chair conformation: a. When the methyl group is in an axial or equatorial (circle one) position, the molecule is inits lowest potential energy conformation. b. Label one Newman projection above anti and the other gauche to describe the relationshipbetween the methyl group and C3 of the ring. c. In general, which is a lower PE conformation, anti or gauche? d. Explain how your answer to b and c provide an explanation for why it is more favorable fora large group to be in an equatorial than an axial position.
(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.
Are e through g isomers, conformers, or stereoisomers?
Draw a three-dimensional structure for each compound, and star all asymmetric carbon atoms. Draw the mirror image for each structure, and state whether you have drawn a pair of enantiomers or just the same molecule twice. Build molecular models of any of these examples that seem difficult to you. (a) ОН (b) (c) NH, ОН СH—CH—СООН | pentan-2-ol pentan-3-ol alanine (d) 1-bromo-2-methylbutane (e) chlorocyclohexane (f) cis-1,2-dichlorocyclobutane (h) (i) H CH; "H H. H CH, H
Give each of the following structures an IUPAC name. (a) (b) H3C H3C² Н2 ОН HC. H2 Н, ОН CH3 (c) (d) НО НО Н, Н, CH ОН C H2 ОН НС. OH CH3
Dehydration of 1,2,2-trimethylcyclohexanol with H2SO4 affords 1-tertbutylcyclopentene as a minor product. (a) Draw a stepwise mechanismthat shows how this alkene is formed. (b) Draw other alkenes formed inthis dehydration. At least one must contain a five-membered ring.
Draw 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, NaOH

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Draw the most stable chair conformation of each of the following compounds. (a) cis-1,1,4- trimethylcyclohexane (B) trans -1,1,3-trimethylcyclohexane (c) cis -1 fluro-4-ethylcyclohexane -