ORGANIC CHEMISTRY-NEXTGEN+BOX (2 SEM.)
ORGANIC CHEMISTRY-NEXTGEN+BOX (2 SEM.)
3rd Edition
ISBN: 9781119497479
Author: Klein
Publisher: WILEY
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Chapter 21, Problem 53PP

(a)

Interpretation Introduction

Interpretation:

The enolate that is formed when the given ketone reacts with LDA has to be drawn.

Concept Introduction:

The structure of LDA :

  ORGANIC CHEMISTRY-NEXTGEN+BOX (2 SEM.), Chapter 21, Problem 53PP , additional homework tip  1

The name LDA stands for Lithiumdiisopropylamide.

Since LDA  is being a bulky base, it always prefers to attack only the less hindered site α-Carbon atom of ketone and forms the enolate which will be resonance stabilized.

Enolate formation:

When ketones are treated with a strong base, the α-position of the ketone will be deprotonated to give a resonance-stabilized intermediate called an enolate.

Example:

ORGANIC CHEMISTRY-NEXTGEN+BOX (2 SEM.), Chapter 21, Problem 53PP , additional homework tip  2

(b)

Interpretation Introduction

Interpretation:

The enolate that is formed when the given ketone reacts with LDA has to be drawn.

Concept Introduction:

The structure of LDA :

  ORGANIC CHEMISTRY-NEXTGEN+BOX (2 SEM.), Chapter 21, Problem 53PP , additional homework tip  3

The name LDA stands for Lithiumdiisopropylamide.

Since LDA  is being a bulky base, it always prefers to attack only the less hindered site α-Carbon atom of ketone and forms the enolate which will be resonance stabilized.

Enolate formation:

When ketones are treated with a strong base, the α-position of the ketone will be deprotonated to give a resonance-stabilized intermediate called an enolate.

Example:

ORGANIC CHEMISTRY-NEXTGEN+BOX (2 SEM.), Chapter 21, Problem 53PP , additional homework tip  4

(c)

Interpretation Introduction

Interpretation:

The enolate that is formed when the given ketone reacts with ORGANIC CHEMISTRY-NEXTGEN+BOX (2 SEM.), Chapter 21, Problem 53PP , additional homework tip  5 has to be drawn.

Concept Introduction:

The structure of LDA :

  ORGANIC CHEMISTRY-NEXTGEN+BOX (2 SEM.), Chapter 21, Problem 53PP , additional homework tip  6

The name LDA stands for Lithiumdiisopropylamide.

Since LDA  is being a bulky base, it always prefers to attack only the less hindered site α-Carbon atom of ketone and forms the enolate which will be resonance stabilized.

Enolate formation:

When ketones are treated with a strong base, the α-position of the ketone will be deprotonated to give a resonance-stabilized intermediate called an enolate.

Example:

ORGANIC CHEMISTRY-NEXTGEN+BOX (2 SEM.), Chapter 21, Problem 53PP , additional homework tip  7

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What spectral features allow you to differentiate the product from the starting material? Use four separate paragraphs for each set of comparisons. You should have one paragraph each devoted to MS, HNMR, CNMR and IR. 2) For MS, the differing masses of molecular ions are a popular starting point. Including a unique fragmentation is important, too. 3) For HNMR, CNMR and IR state the peaks that are different and what makes them different (usually the presence or absence of certain groups). See if you can find two differences (in each set of IR, HNMR and CNMR spectra) due to the presence or absence of a functional group. Include peak locations. Alternatively, you can state a shift of a peak due to a change near a given functional group. Including peak locations for shifted peaks, as well as what these peaks are due to. Ideally, your focus should be on not just identifying the differences but explaining them in terms of functional group changes.

Chapter 21 Solutions

ORGANIC CHEMISTRY-NEXTGEN+BOX (2 SEM.)

Ch. 21.2 - Prob. 10CCCh. 21.2 - Prob. 11CCCh. 21.2 - Prob. 12CCCh. 21.2 - Prob. 13CCCh. 21.3 - Prob. 2LTSCh. 21.3 - Prob. 14PTSCh. 21.3 - Prob. 15PTSCh. 21.3 - Prob. 16ATSCh. 21.3 - Prob. 3LTSCh. 21.3 - Prob. 17PTSCh. 21.3 - Prob. 18ATSCh. 21.3 - Prob. 4LTSCh. 21.3 - Prob. 19PTSCh. 21.3 - Prob. 20ATSCh. 21.3 - Prob. 21CCCh. 21.3 - Prob. 22CCCh. 21.3 - Prob. 23CCCh. 21.4 - Prob. 24CCCh. 21.4 - Prob. 25CCCh. 21.4 - Prob. 26CCCh. 21.4 - Prob. 27CCCh. 21.4 - Prob. 28CCCh. 21.5 - Prob. 29CCCh. 21.5 - Prob. 30CCCh. 21.5 - Prob. 5LTSCh. 21.5 - Prob. 31PTSCh. 21.5 - Prob. 32ATSCh. 21.5 - Prob. 6LTSCh. 21.5 - Prob. 33PTSCh. 21.5 - Prob. 34ATSCh. 21.6 - Prob. 35CCCh. 21.6 - Prob. 36CCCh. 21.6 - Prob. 37CCCh. 21.6 - Prob. 7LTSCh. 21.6 - Prob. 38PTSCh. 21.6 - Prob. 39ATSCh. 21.6 - Prob. 40CCCh. 21.6 - Prob. 41CCCh. 21.7 - Prob. 8LTSCh. 21.7 - Prob. 42PTSCh. 21.7 - Prob. 43PTSCh. 21.7 - Prob. 9LTSCh. 21.7 - Prob. 45PTSCh. 21.7 - Prob. 46ATSCh. 21 - Prob. 47PPCh. 21 - Prob. 48PPCh. 21 - Prob. 49PPCh. 21 - Prob. 50PPCh. 21 - Prob. 51PPCh. 21 - Prob. 52PPCh. 21 - Prob. 53PPCh. 21 - Prob. 54PPCh. 21 - Prob. 55PPCh. 21 - Prob. 56PPCh. 21 - Prob. 57PPCh. 21 - Prob. 58PPCh. 21 - Prob. 59PPCh. 21 - Prob. 60PPCh. 21 - Prob. 61PPCh. 21 - Prob. 62PPCh. 21 - Prob. 63PPCh. 21 - Prob. 64PPCh. 21 - Prob. 65PPCh. 21 - Prob. 66PPCh. 21 - Prob. 67PPCh. 21 - Prob. 68PPCh. 21 - Prob. 69PPCh. 21 - Prob. 70PPCh. 21 - Prob. 71PPCh. 21 - Prob. 72PPCh. 21 - Prob. 73PPCh. 21 - Prob. 74PPCh. 21 - Prob. 75PPCh. 21 - Prob. 76PPCh. 21 - Prob. 77PPCh. 21 - Prob. 78PPCh. 21 - Prob. 79PPCh. 21 - Prob. 80PPCh. 21 - Prob. 81PPCh. 21 - Prob. 82PPCh. 21 - Prob. 83PPCh. 21 - Prob. 84PPCh. 21 - Prob. 85PPCh. 21 - Prob. 86PPCh. 21 - Prob. 87PPCh. 21 - Prob. 88PPCh. 21 - Prob. 89IPCh. 21 - Prob. 90IPCh. 21 - Prob. 91IPCh. 21 - Prob. 92IPCh. 21 - Prob. 93IPCh. 21 - Prob. 94IPCh. 21 - Prob. 95IPCh. 21 - Prob. 96IPCh. 21 - Prob. 97IPCh. 21 - Prob. 98IPCh. 21 - Prob. 99IPCh. 21 - Prob. 100IPCh. 21 - Prob. 101IPCh. 21 - Prob. 102IPCh. 21 - Prob. 103IPCh. 21 - Prob. 104IPCh. 21 - Prob. 105IPCh. 21 - Prob. 106IPCh. 21 - Prob. 107IPCh. 21 - Prob. 108IPCh. 21 - Prob. 109IPCh. 21 - Prob. 110IPCh. 21 - Prob. 111IPCh. 21 - Prob. 112IPCh. 21 - Prob. 113IPCh. 21 - Prob. 114IPCh. 21 - Prob. 115IPCh. 21 - Prob. 116CPCh. 21 - Prob. 117CPCh. 21 - Prob. 118CP
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