ORG.CHEM EBOOK W/BBWILEY PLUS>CUSTOM<
ORG.CHEM EBOOK W/BBWILEY PLUS>CUSTOM<
2nd Edition
ISBN: 9781118872925
Author: Klein
Publisher: JOHN WILEY+SONS INC.CUSTOM
Question
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Chapter 20, Problem 71PP

 (a)

Interpretation Introduction

Interpretation:

The given starting compounds and selective reagents used to accomplish the target products transformation should be draw and identified.

Concept introduction:

Wittig reaction: This process allows the preparation of an alkene by the reaction of an aldehyde ( -CHO ) or ketone ( -C=O ) with ylides generated from a phosphonium salt. The geometry of the resulting cis, trans alkene depends on the reactivity of the ylide.

Markovnikov addition: The addition reaction of parotic acids to a different alkene or alkyne, the hydrogen atom of H-X becomes bonded to the carbon atom that the greatest number of hydrogen atoms in the starting alkene or alkyne.

Grignard Reaction: This is a organometallic reaction in different alkyl, aryl-magnesium halides add to a carbonyl group in an aldehyde and ketone. This reaction is an important for the conversion of carbon-carbon single (-C-C-) bond. Moreover the addition of a reagent to an aster, lactone gives a tertiary alcohol in which wo alkyl groups are the same and the addition of a Grignard reagent to a nitrile produces an unsymmetrical ketone.

NaBH4 Reduction: The saturated/unsaturated aldehyde and ketones in the presence of sodium metal in NaBH4 and carbonyl compound produced saturated alcohols. The keto group involves in the reduction process of NaBH4, this end up reducing to give the alcohols.

Acid Catalyzed Hydration Reaction: The reaction involves breaking of π-bonds between carbon-carbon multiple bonds and addition of alcohol to more substituted position of carbon in the molecule.

Addition Reaction: It is defined as chemical reaction in which two given molecules combines and forms product. The types of addition reactions are electrophilic addition, nucleophilic addition, free radical additions and cycloadditions. Generally, compounds with carbon-hetero atom bonds favors addition reaction.

To identify: The reagents used to accomplish the given transformation.

(b)

Interpretation Introduction

Interpretation:

The given starting compounds and selective reagents used to accomplish the target products transformation should be draw and identified.

Concept introduction:

Wittig reaction: This process allows the preparation of an alkene by the reaction of an aldehyde ( -CHO ) or ketone ( -C=O ) with ylides generated from a phosphonium salt. The geometry of the resulting cis, trans alkene depends on the reactivity of the ylide.

Markovnikov addition: The addition reaction of parotic acids to a different alkene or alkyne, the hydrogen atom of H-X becomes bonded to the carbon atom that the greatest number of hydrogen atoms in the starting alkene or alkyne.

Grignard Reaction: This is a organometallic reaction in different alkyl, aryl-magnesium halides add to a carbonyl group in an aldehyde and ketone. This reaction is an important for the conversion of carbon-carbon single (-C-C-) bond. Moreover the addition of a reagent to an aster, lactone gives a tertiary alcohol in which wo alkyl groups are the same and the addition of a Grignard reagent to a nitrile produces an unsymmetrical ketone.

NaBH4 Reduction: The saturated/unsaturated aldehyde and ketones in the presence of sodium metal in NaBH4 and carbonyl compound produced saturated alcohols. The keto group involves in the reduction process of NaBH4, this end up reducing to give the alcohols.

Acid Catalyzed Hydration Reaction: The reaction involves breaking of π-bonds between carbon-carbon multiple bonds and addition of alcohol to more substituted position of carbon in the molecule.

Addition Reaction: It is defined as chemical reaction in which two given molecules combines and forms product. The types of addition reactions are electrophilic addition, nucleophilic addition, free radical additions and cycloadditions. Generally, compounds with carbon-hetero atom bonds favors addition reaction.

To identify: The reagents used to accomplish the given transformation.

(c)

Interpretation Introduction

Interpretation:

The given starting compounds and selective reagents used to accomplish the target products transformation should be draw and identified.

Concept introduction:

Wittig reaction: This process allows the preparation of an alkene by the reaction of an aldehyde ( -CHO ) or ketone ( -C=O ) with ylides generated from a phosphonium salt. The geometry of the resulting cis, trans alkene depends on the reactivity of the ylide.

Markovnikov addition: The addition reaction of parotic acids to a different alkene or alkyne, the hydrogen atom of H-X becomes bonded to the carbon atom that the greatest number of hydrogen atoms in the starting alkene or alkyne.

Grignard Reaction: This is a organometallic reaction in different alkyl, aryl-magnesium halides add to a carbonyl group in an aldehyde and ketone. This reaction is an important for the conversion of carbon-carbon single (-C-C-) bond. Moreover the addition of a reagent to an aster, lactone gives a tertiary alcohol in which wo alkyl groups are the same and the addition of a Grignard reagent to a nitrile produces an unsymmetrical ketone.

NaBH4 Reduction: The saturated/unsaturated aldehyde and ketones in the presence of sodium metal in NaBH4 and carbonyl compound produced saturated alcohols. The keto group involves in the reduction process of NaBH4, this end up reducing to give the alcohols.

Acid Catalyzed Hydration Reaction: The reaction involves breaking of π-bonds between carbon-carbon multiple bonds and addition of alcohol to more substituted position of carbon in the molecule.

Addition Reaction: It is defined as chemical reaction in which two given molecules combines and forms product. The types of addition reactions are electrophilic addition, nucleophilic addition, free radical additions and cycloadditions. Generally, compounds with carbon-hetero atom bonds favors addition reaction.

To identify: The reagents used to accomplish the given transformation.

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Part VII. Below are the 'HNMR, 13 C-NMR, COSY 2D- NMR, and HSQC 2D-NMR (similar with HETCOR but axes are reversed) spectra of an organic compound with molecular formula C6H1003 - Assign chemical shift values to the H and c atoms of the compound. Find the structure. Show complete solutions. Predicted 1H NMR Spectrum 4.7 4.6 4.5 4.4 4.3 4.2 4.1 4.0 3.9 3.8 3.7 3.6 3.5 3.4 3.3 3.2 3.1 3.0 2.9 2.8 2.7 2.6 2.5 2.4 2.3 2.2 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4 1.3 1.2 1.1 f1 (ppm) Predicted 13C NMR Spectrum 100 f1 (ppm) 30 220 210 200 190 180 170 160 150 140 130 120 110 90 80 70 -26 60 50 40 46 30 20 115 10 1.0 0.9 0.8 0 -10
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None

Chapter 20 Solutions

ORG.CHEM EBOOK W/BBWILEY PLUS>CUSTOM<

Ch. 20.5 - Prob. 12CCCh. 20.5 - Prob. 13CCCh. 20.5 - Prob. 14CCCh. 20.6 - Prob. 3LTSCh. 20.6 - Prob. 15PTSCh. 20.6 - Prob. 16ATSCh. 20.6 - Prob. 17ATSCh. 20.6 - Prob. 18ATSCh. 20.6 - Prob. 19CCCh. 20.6 - Prob. 20CCCh. 20.6 - Prob. 4LTSCh. 20.6 - Prob. 21PTSCh. 20.6 - Prob. 22ATSCh. 20.6 - Prob. 23ATSCh. 20.6 - Prob. 24ATSCh. 20.7 - Prob. 5LTSCh. 20.7 - Prob. 26PTSCh. 20.7 - Prob. 27ATSCh. 20.7 - Prob. 28CCCh. 20.8 - Prob. 29CCCh. 20.8 - Prob. 30CCCh. 20.9 - Prob. 31CCCh. 20.9 - Prob. 32CCCh. 20.10 - Prob. 33CCCh. 20.10 - Prob. 34CCCh. 20.10 - Prob. 35CCCh. 20.10 - Prob. 36CCCh. 20.10 - Prob. 6LTSCh. 20.10 - Prob. 37PTSCh. 20.10 - Prob. 38ATSCh. 20.10 - Prob. 39ATSCh. 20.11 - Prob. 40CCCh. 20.12 - Prob. 7LTSCh. 20.12 - Prob. 41PTSCh. 20.12 - Prob. 42PTSCh. 20.13 - Prob. 43CCCh. 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. 70PPCh. 20 - Prob. 71PPCh. 20 - Prob. 72PPCh. 20 - Prob. 73PPCh. 20 - Prob. 74PPCh. 20 - Prob. 75PPCh. 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 - Prob. 85IPCh. 20 - Prob. 86IP
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