ORGANIC CHEMISTRY WILEYPLUS ACCESS>I<
4th Edition
ISBN: 9781119850151
Author: Klein
Publisher: WILEY
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Chapter 6.10, Problem 16ATS
Interpretation Introduction
Interpretation: The missing lone pairs and curved arrows along with the arrow pushing pattern are to be interpreted for the reaction of indolizomycin with triphenylphosphine
Concept introduction: In a
Electrophiles have a positive charge and are attracted toward an electronegative center. On the contrary, nucleophiles carry a negative charge and are attracted toward the electropositive center.
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Consider the following nucleophilic substitution reaction. The compound listed above the arrow is the solvent for the reaction. If nothing is listed over the arrow,
then the nucleophile is also the solvent for the reaction.
Part 1 of 2
Br
CH,CN
+ I¯
What is the correct mechanism for the reaction? Select the single best answer.
@SN2
○ SN 1
Part: 1/2
Part 2 of 2
Draw the products for the reaction. Include both the major organic product and the inorganic product. If more than one stereoisomer is possible, draw
only one stereoisomer. Include stereochemistry where relevant.
Click and drag to start drawing a
structure.
X
હૈ
20.33 Think-Pair-Share
(a) Rank the following dienes and dienophiles in order of increasing reactivity in the
Diels-Alder reaction.
(i)
CO₂Et
(ii)
COEt
||
CO₂Et
MeO
MeO
(b) Draw the product that results from the most reactive diene and most reactive
dienophile shown in part (a).
(c) Draw a depiction of the orbital overlap involved in the pericyclic reaction that oc-
curs between the diene and dienophile in part (b).
(d) Is the major product formed in part (b) the endo or exo configuration? Explain
your reasoning.
20.40 The following compound undergoes an intramolecular Diels-Alder reaction to give a
tricyclic product. Propose a structural formula for the product.
CN
heat
An intramolecular
Diels-Alder adduct
Chapter 6 Solutions
ORGANIC CHEMISTRY WILEYPLUS ACCESS>I<
Ch. 6.1 - Prob. 1LTSCh. 6.1 - Prob. 1PTSCh. 6.1 - Prob. 2ATSCh. 6.2 - Prob. 3CCCh. 6.3 - Prob. 4CCCh. 6.3 - Prob. 5CCCh. 6.4 - Prob. 6CCCh. 6.6 - Prob. 7CCCh. 6.7 - Prob. 2LTSCh. 6.7 - Prob. 8PTS
Ch. 6.7 - Prob. 9PTSCh. 6.7 - Prob. 10ATSCh. 6.8 - Prob. 3LTSCh. 6.8 - Prob. 11PTSCh. 6.8 - Prob. 12ATSCh. 6.9 - Prob. 4LTSCh. 6.9 - Prob. 13PTSCh. 6.9 - Prob. 14ATSCh. 6.10 - Prob. 5LTSCh. 6.10 - Prob. 15PTSCh. 6.10 - Prob. 16ATSCh. 6.11 - Prob. 6LTSCh. 6.11 - Prob. 17PTSCh. 6.11 - Prob. 18ATSCh. 6 - Prob. 19PPCh. 6 - Prob. 20PPCh. 6 - Prob. 21PPCh. 6 - Prob. 22PPCh. 6 - Prob. 24PPCh. 6 - Prob. 25PPCh. 6 - Prob. 26PPCh. 6 - Prob. 27PPCh. 6 - Prob. 28PPCh. 6 - Prob. 29PPCh. 6 - Prob. 30PPCh. 6 - Prob. 31PPCh. 6 - Prob. 32PPCh. 6 - Prob. 33PPCh. 6 - Prob. 34PPCh. 6 - Prob. 35PPCh. 6 - Prob. 36PPCh. 6 - Prob. 37PPCh. 6 - Prob. 38PPCh. 6 - Prob. 39PPCh. 6 - Prob. 40PPCh. 6 - Prob. 41PPCh. 6 - Prob. 43ASPCh. 6 - Prob. 44ASPCh. 6 - Prob. 45ASPCh. 6 - Prob. 46ASPCh. 6 - Prob. 47ASPCh. 6 - Prob. 48ASPCh. 6 - Prob. 49ASPCh. 6 - Prob. 50IPCh. 6 - Prob. 51IPCh. 6 - Prob. 52IPCh. 6 - Prob. 53IPCh. 6 - Prob. 54IPCh. 6 - Prob. 55IPCh. 6 - Prob. 56IPCh. 6 - Prob. 57IPCh. 6 - Prob. 58IPCh. 6 - Prob. 59IPCh. 6 - Prob. 60IPCh. 6 - Prob. 61IPCh. 6 - Prob. 62CPCh. 6 - Prob. 64CP
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- What is the reaction mechanism for this?arrow_forwardWhat is the reaction mechanism for this?arrow_forwardCurved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. + Drawing Arrows CH3ONA, CH3OH heat : Br:O Na → H H Br Na + H H H H H :0: .H + Undo Reset Done Q CH3 Drag To Pan +arrow_forward
- What is the reaction mechanism for this?arrow_forward20.19 Predict the structure of the major 1,2-addition product formed by reaction of one mole of Cl₂ with 3-methylenecyclohexene. Also predict the structure of the 1,4-addition product formed under these conditions. 20.20 Which of the two molecules shown do you expect to be the major product formed by 1,2-addition of HCI to cyclopentadiene? Explain. Cyclopentadiene + HC 3-Chlorocyclopentene (racemic) or 4-Chlorocyclopentene (racemic)arrow_forward20.35 Propose structural formulas for compounds A and B and specify the configuration of compound B. EtO₂C 250°C C14H2004 CO₂Et 1. Oso, then NaHSO3 2. HIO4 C14H2006 A Barrow_forward
- 20.21 Predict the major product formed by 1,4-addition of HCI to cyclopentadiene. 20.22 Draw structural formulas for the two constitutional isomers with the molecular for- mula C₂H,Br, formed by adding one mole of Br, to cyclopentadiene.arrow_forwardAdd substituents to draw the conformer below (sighting down the indicated bond), then rotate the back carbon to provide the conformation that will be capable of an E2 elimination. R/S stereochemistry is graded. + I I H CH3 Ph Досн Br OCH 3 Drawing Q H Atoms, Bonds and Rings Charges Tap a node to see suggestions. H H H H H Undo Reset Remove Done Rotatearrow_forward20.17 Predict the structure of the major product formed by 1,2-addition of HBr to 3-methylenecyclohexene. 3-Methylenecyclohexene 20.18 Predict the major product formed by 1,4-addition of HBr to 3-methylenecyclohexene.arrow_forward
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