(a) Interpretation: How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown. Concept introduction: A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

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Answer 1

Question

Chapter 19, Problem 19.40P

Interpretation Introduction

(a)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

Interpretation Introduction

(b)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

Interpretation Introduction

(c)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

Interpretation Introduction

(d)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

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Commercial bleach contains either chlorine or oxygen as an active ingredient. A commercial oxygenated bleach is much safer to handle and less likely to ruin your clothes. It is possible to determine the amount of active ingredient in an oxygenated bleach product by performing a redox titration. The balance reaction for such a titration is: 6H+ +5H2O2 +2MnO4- à 5O2 + 2Mn2+ + 8H2O If you performed the following procedure: “First, dilute the Seventh Generation Non-Chlorine Bleach by pipetting 10 mL of bleach in a 100 mL volumetric flask and filling the flask to the mark with distilled water. Next, pipet 10 mL of the diluted bleach solution into a 250 mL Erlenmeyer flask and add 20 mL of 1.0 M H2SO4 to the flask. This solution should be titrated with 0.0100 M KMnO4 solution.” It took 18.47mL of the KMnO4 to reach the endpoint on average. What was the concentration of H2O2 in the original bleach solution in weight % assuming the density of bleach is 1g/mL?

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Proper care of pH electrodes: Why can you not store a pH electrode in distilled water? What must you instead store it in? Why?

Answer 2

Question

Chapter 19, Problem 19.40P

Interpretation Introduction

(a)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

Interpretation Introduction

(b)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

Interpretation Introduction

(c)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

Interpretation Introduction

(d)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

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Answer 3

Question

Chapter 19, Problem 19.40P

Interpretation Introduction

(a)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

Interpretation Introduction

(b)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

Interpretation Introduction

(c)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

Interpretation Introduction

(d)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

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Answer 4

Question

Chapter 19, Problem 19.40P

Interpretation Introduction

(a)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

Interpretation Introduction

(b)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

Interpretation Introduction

(c)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

Interpretation Introduction

(d)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

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Answer 5

Chapter 19, Problem 19.40P

Interpretation Introduction

(a)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

Interpretation Introduction

(b)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

Interpretation Introduction

(c)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

Interpretation Introduction

(d)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

Answer 6

Chapter 19, Problem 19.40P

Interpretation Introduction

(a)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

Answer 7

Chapter 19, Problem 19.40P

Interpretation Introduction

(a)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

Answer 8

Interpretation Introduction

(b)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

Answer 9

Interpretation Introduction

(b)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

Answer 10

Interpretation Introduction

(c)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

Answer 11

Interpretation Introduction

(c)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

Answer 12

Interpretation Introduction

(d)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

Answer 13

Interpretation Introduction

(d)

Interpretation:

How the given lithium dialkylcuprate reagent can be synthesized from an alkyl, alkenyl, alkynyl, or aryl halide is to be shown.

Concept introduction:

A lithium dialkylcuprate is synthesized from the corresponding alkyllithium reagent by treating it with copper(I) iodide, CuI. Because the metal-bonded C atom bears a partial negative charge on both the alkyllithium reagent and the lithium dialkylcuprate, umpolung technically does not occur in this reaction, but synthesizing a lithium dialkylcuprate from an alkyl halide does represent polarity reversal at the C atom. The C atom bonded to Cu should be bonded to halide. The carbon atom of C-X bond is electron poor whereas the carbon of C-Cu bond is electron rich.

Answer 14

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Answer 15

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Answer 16

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Answer 17

Ch. 19 - Prob. 19.1P Ch. 19 - Prob. 19.2P Ch. 19 - Prob. 19.3P Ch. 19 - Prob. 19.4P Ch. 19 - Prob. 19.5P Ch. 19 - Prob. 19.6P Ch. 19 - Prob. 19.7P Ch. 19 - Prob. 19.8P Ch. 19 - Prob. 19.9P Ch. 19 - Prob. 19.10P

Solution Summary: The author explains how a lithium dialkylcuprate reagent can be synthesized from an alkenyl halide.

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