(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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2. 200 LOD For an unknown compound with a molecular ion of 101 m/z: a. Use the molecular ion to propose at least two molecular formulas. (show your work) b. What is the DU for each of your possible formulas? (show your work) C. Solve the structure and assign each of the following spectra. 8 6 4 2 (ppm) 150 100 50 ō (ppm) 4000 3000 2000 1500 1000 500 HAVENUMBERI-11

Complete the spectroscopy with structure

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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