ORGANIC CHEMISTRY-PRINT COMPANION (LL)
ORGANIC CHEMISTRY-PRINT COMPANION (LL)
3rd Edition
ISBN: 9781119444251
Author: Klein
Publisher: WILEY
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Chapter 20, Problem 92CP
Interpretation Introduction

Interpretation: For the given formation of epoxide and bromohydrin, a plausible mechanism has to be provided.

Concept Introduction:

 For any given transformation, the following mandatory observations have to be made clear to predict the synthetic scheme:

  • Observe whether there is any change in the carbon skeleton.
  • Observe whether there is any change in the location of the functional group.
  • Predict the synthetic scheme in such a way that these two observations have to be achieved within the minimum chemo selective steps.

The given transformation is:

ORGANIC CHEMISTRY-PRINT COMPANION (LL), Chapter 20, Problem 92CP

SN2 reaction:

The alcohols is reaction with acids like hydrochloric acid or hydrobromic acid, the bromine atom attacks back side of the carbon atoms which is bearing alcohol group which yield the corresponding inversion product.

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3. SYNTHESIS. Propose a sequence of synthetic steps (FGI) that convert the starting material (SM) into the Target molecule. For each FGI in your proposed synthesis, specify the reagents / conditions, and draw the product(s) of that FGI. DO NOT INCLUDE the FGI mxn in the answer you submit. If an FGI requires two reagent sets, specify the order in which the reagent sets are added, e.g., i) Hg(OAc)2 / H₂O; ii) NaBH4/MeOH. Indicate the stereochemistry (if any) of the products of each FGI. FGI 1. Me Starting Material Source of all carbons in the Target molecule (can use multiple copies) Me Me Target molecule + enantiomer
curved arrows are used to illustate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction mechanism steps

Chapter 20 Solutions

ORGANIC CHEMISTRY-PRINT COMPANION (LL)

Ch. 20.5 - Prob. 11CCCh. 20.6 - Prob. 12CCCh. 20.6 - Prob. 13CCCh. 20.7 - Prob. 1LTSCh. 20.7 - Prob. 14PTSCh. 20.7 - Prob. 15ATSCh. 20.8 - Prob. 16CCCh. 20.8 - Prob. 17CCCh. 20.8 - Prob. 18CCCh. 20.9 - Prob. 19CCCh. 20.10 - Prob. 20CCCh. 20.10 - Prob. 21CCCh. 20.11 - Prob. 22CCCh. 20.11 - Prob. 23CCCh. 20.12 - Prob. 24CCCh. 20.12 - Prob. 25CCCh. 20.12 - Prob. 26CCCh. 20.13 - Prob. 27CCCh. 20.13 - Prob. 28CCCh. 20.13 - Prob. 29CCCh. 20.14 - Prob. 2LTSCh. 20.14 - Prob. 30PTSCh. 20.14 - Prob. 31ATSCh. 20.14 - Prob. 3LTSCh. 20.14 - Prob. 32PTSCh. 20.14 - Prob. 33ATSCh. 20.15 - Prob. 34CCCh. 20 - Prob. 35PPCh. 20 - Prob. 36PPCh. 20 - Prob. 37PPCh. 20 - Prob. 38PPCh. 20 - Prob. 39PPCh. 20 - Prob. 40PPCh. 20 - Prob. 41PPCh. 20 - Prob. 42PPCh. 20 - Prob. 43PPCh. 20 - Prob. 44PPCh. 20 - Prob. 45PPCh. 20 - Prob. 46PPCh. 20 - Prob. 47PPCh. 20 - Prob. 48PPCh. 20 - Prob. 49PPCh. 20 - Prob. 50PPCh. 20 - Prob. 51PPCh. 20 - Prob. 52PPCh. 20 - Prob. 53PPCh. 20 - Prob. 54PPCh. 20 - Prob. 55PPCh. 20 - Prob. 56PPCh. 20 - Prob. 57PPCh. 20 - Prob. 58PPCh. 20 - Prob. 59PPCh. 20 - Prob. 60PPCh. 20 - Prob. 61PPCh. 20 - Prob. 62PPCh. 20 - Prob. 63PPCh. 20 - Prob. 64PPCh. 20 - Prob. 65PPCh. 20 - Prob. 66PPCh. 20 - Prob. 67PPCh. 20 - Prob. 68PPCh. 20 - Prob. 69PPCh. 20 - Prob. 70IPCh. 20 - Prob. 72IPCh. 20 - Prob. 73IPCh. 20 - Prob. 74IPCh. 20 - Prob. 75IPCh. 20 - Prob. 76IPCh. 20 - Prob. 77IPCh. 20 - Prob. 78IPCh. 20 - Prob. 79IPCh. 20 - Prob. 80IPCh. 20 - Prob. 81IPCh. 20 - Prob. 82IPCh. 20 - Prob. 83IPCh. 20 - Prob. 84IPCh. 20 - Compound 3 (below) was used as an intermediate in...Ch. 20 - The m- and p-substituted methyl benzoates listed...Ch. 20 - Prob. 87IPCh. 20 - Prob. 88IPCh. 20 - Prob. 89IPCh. 20 - Prob. 90CPCh. 20 - Prob. 91CPCh. 20 - Prob. 92CPCh. 20 - Prob. 93CP
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