Organic Chemistry Third Edition + Electronic Solutions Manual And Study Guide
Organic Chemistry Third Edition + Electronic Solutions Manual And Study Guide
3rd Edition
ISBN: 9781119351610
Author: David Klein
Publisher: Wiley Plus
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Chapter 6, Problem 33PP
Interpretation Introduction

Interpretation:

The sequences of arrow-pushing pattern in the given reactions have to be identified and compared.

Concept Introduction:

Mechanism of the reaction is the step-by-step description of the process by which reactants are changed into products.

There are only four characteristic patterns, and all ionic mechanisms are simply combinations of these four steps, and they are,

  1. (1) Nucleophilic attack

When we identify a nucleophilic site and an electrophilic site, the arrow in the mechanism step shows the nucleophile attacking.

  1. (2) Proton transfer
  2. (3) Loss of leaving group
  3. (4) Rearrangements

Rearrangements will always occur when an alkyl group or hydrogen can shift to form a more stable carbocation. There are mainly two types of rearrangement shifts and they are,

1, 2-methyl shift1, 2-hydride shift

Curved arrows show the bonds that are formed and the bonds that are broken in a reaction.

Curved arrows used to understand a reaction mechanism.

Curved arrows are drawn to show how the electrons move as new covalent bonds are formed existing covalent bonds are broken.

Each arrow represents the simultaneous movement of two electrons from a nucleophile towards an electrophile.

Nucleophile: It is negatively charged species which seeks for positive charge and hence donate pair of electrons to positively charged species (electrophiles) which results in the formation of chemical bond.

In nucleophilic substitution reaction a nucleophile is the species with an unshared electron pair which reacts with an electron deficient carbon. And so the leaving group is substituted by a nucleophile.

Ipso substitution reaction: It is the one of the aromatic substitution reaction in which both the substituent (nucleophile and the parent substituent) present in the same ring position in an intermediate compound. Finally the parent substituent leave from the intermediate leads to the formation of product.

The mechanism of desulfonation curved arrow pattern is given below.

Organic Chemistry Third Edition + Electronic Solutions Manual And Study Guide, Chapter 6, Problem 33PP

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%Reflectance 95 90- 85 22 00 89 60 55 50 70 65 75 80 50- 45 40 WA 35 30- 25 20- 4000 3500 Date: Thu Feb 06 17:21:21 2025 (GMT-05:0(UnknownD Scans: 8 Resolution: 2.000 3000 2500 Wavenumbers (cm-1) 100- 2981.77 1734.25 2000 1500 1000 1372.09 1108.01 2359.09 1469.82 1181.94 1145.20 1017.01 958.45 886.97 820.49 668.25 630.05 611.37
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CH3 CH H3C CH3 H OH H3C- -OCH2CH3 H3C H -OCH3 For each of the above compounds, do the following: 1. List the wave numbers of all the IR bands in the 1350-4000 cm-1 region. For each one, state what bond or group it represents. 2. Label equivalent sets of protons with lower-case letters. Then, for each 1H NMR signal, give the 8 value, the type of splitting (singlet, doublet etc.), and the number protons it represents. of letter δ value splitting # of protons 3. Redraw the compound and label equivalent sets of carbons with lower-case letters. Then for each set of carbons give the 5 value and # of carbons it represents. letter δ value # of carbons

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