(a) Interpretation: The major product of the reaction is to be predicted. Concept introduction: Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyllithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R - nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

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LTS Solid: AT=Te-Ti Trial 1 Trial 2 Trial 3 Average ΔΗ Mass water, g 24.096 23.976 23.975 Moles of solid, mol 0.01763 001767 0101781 Temp. change, °C 2.9°C 11700 2.0°C Heat of reaction, J -292.37J -170.473 -193.26J AH, kJ/mole 16.58K 9.647 kJ 10.85 kr 16.58K59.64701 KJ mol 12.35k Minimum AS, J/mol K 41.582 mol-k Remember: q = mCsAT (m = mass of water, Cs=4.184J/g°C) & qsin =-qrxn & Show your calculations for: AH in J and then in kJ/mole for Trial 1: qa (24.0969)(4.1845/g) (-2.9°C)=-292.37J qsin = qrxn = 292.35 292.37J AH in J = 292.375 0.2923kJ 0.01763m01 =1.65×107 AH in kJ/mol = = 16.58K 0.01763mol mol qrx Minimum AS in J/mol K (Hint: use the average initial temperature of the three trials, con Kelvin.) AS=AHIT (1.65×10(9.64×103) + (1.0 Jimai

Answer 1

Question

Chapter 17, Problem 17.29P

Interpretation Introduction

(a)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyllithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Interpretation Introduction

(b)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Interpretation Introduction

(c)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

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LTS Solid: AT=Te-Ti Trial 1 Trial 2 Trial 3 Average ΔΗ Mass water, g 24.096 23.976 23.975 Moles of solid, mol 0.01763 001767 0101781 Temp. change, °C 2.9°C 11700 2.0°C Heat of reaction, J -292.37J -170.473 -193.26J AH, kJ/mole 16.58K 9.647 kJ 10.85 kr 16.58K59.64701 KJ mol 12.35k Minimum AS, J/mol K 41.582 mol-k Remember: q = mCsAT (m = mass of water, Cs=4.184J/g°C) & qsin =-qrxn & Show your calculations for: AH in J and then in kJ/mole for Trial 1: qa (24.0969)(4.1845/g) (-2.9°C)=-292.37J qsin = qrxn = 292.35 292.37J AH in J = 292.375 0.2923kJ 0.01763m01 =1.65×107 AH in kJ/mol = = 16.58K 0.01763mol mol qrx Minimum AS in J/mol K (Hint: use the average initial temperature of the three trials, con Kelvin.) AS=AHIT (1.65×10(9.64×103) + (1.0 Jimai

For the compound: C8H17NO2 Use the following information to come up with a plausible structure: 8 This compound has "carboxylic acid amide" and ether functional groups. The peaks at 1.2ppm are two signals that are overlapping one another. One of the two signals is a doublet that represents 6 hydrogens; the other signal is a quartet that represents 3 hydrogens.

Vnk the elements or compounds in the table below in decreasing order of their boiling points. That is, choose 1 next to the substance with the highest bolling point, choose 2 next to the substance with the next highest boiling point, and so on. substance C D chemical symbol, chemical formula or Lewis structure. CH,-N-CH, CH, H H 10: H C-C-H H H H Cale H 10: H-C-C-N-CH, Bri CH, boiling point (C) Сен (C) B (Choose

Answer 2

Question

Chapter 17, Problem 17.29P

Interpretation Introduction

(a)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyllithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Interpretation Introduction

(b)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Interpretation Introduction

(c)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

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Answer 3

Question

Chapter 17, Problem 17.29P

Interpretation Introduction

(a)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyllithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Interpretation Introduction

(b)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Interpretation Introduction

(c)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

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Answer 4

Question

Chapter 17, Problem 17.29P

Interpretation Introduction

(a)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyllithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Interpretation Introduction

(b)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Interpretation Introduction

(c)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

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Answer 5

Chapter 17, Problem 17.29P

Interpretation Introduction

(a)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyllithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Interpretation Introduction

(b)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Interpretation Introduction

(c)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Answer 6

Chapter 17, Problem 17.29P

Interpretation Introduction

(a)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyllithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Answer 7

Chapter 17, Problem 17.29P

Interpretation Introduction

(a)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyllithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Answer 8

Interpretation Introduction

(b)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Answer 9

Interpretation Introduction

(b)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Answer 10

Interpretation Introduction

(c)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

Answer 11

Interpretation Introduction

(c)

Interpretation:

The major product of the reaction is to be predicted.

Concept introduction:

Grignard reagents and alkyl lithium undergo direct addition to α,β-unsaturated carbonyls. Along with the direct addition product, they also produce a minor amount of conjugate addition product. Alkyl lithium reagents generally have a greater tendency toward 1, 2-addition to α,β- unsaturated carbonyls than Grignard reagents do. Alkyl lithium reagent produces less of the conjugate addition product. This greater selectivity of alkyl lithium reagents is explained by the greater concentration of negative charge on C. Thus, in the kinetically controlled addition of R- nucleophile, alkyl lithium reagents react faster with the carbonyl carbon than do Grignard reagents. The anion produced during direct addition is then protonated to obtain the final product.

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Answer 23

Ch. 17 - Prob. 17.1P Ch. 17 - Prob. 17.2P Ch. 17 - Prob. 17.3P Ch. 17 - Prob. 17.4P Ch. 17 - Prob. 17.5P Ch. 17 - Prob. 17.6P Ch. 17 - Prob. 17.7P Ch. 17 - Prob. 17.8P Ch. 17 - Prob. 17.9P Ch. 17 - Prob. 17.10P

Solution Summary: The author explains that Grignard reagents and alkyl lithium undergo direct addition to,-unsaturated carbonyls.

Chapter 17 Solutions