(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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9 7 8 C 9 8 200 190 B 5 A -197.72 9 8 7 15 4 3 0: ང་ 200 190 180 147.52 134.98 170 160 150 140 130 120 110 100 90 90 OH 10 4 3 1 2 -143.04 140. 180 170 160 150 140 130 120 110 100 90 CI 3 5 1 2 141.89 140.07 200 190 180 170 160 150 140 130 120 110 100 ៖- 90 129. 126.25 80 70 60 -60 50 40 10 125.19 -129.21 80 70 3.0 20 20 -8 60 50 10 ppm -20 40 128.31 80 80 70 60 50 40 40 -70.27 3.0 20 10 ppm 00˚0-- 77.17 30 20 20 -45.36 10 ppm -0.00 26.48 22.32 ―30.10 ―-0.00

Assign all the carbons

C 5 4 3 CI 2 the Righ B A 5 4 3 The Lich. OH 10 4 5 3 1 LOOP- -147.52 T 77.17 -45.36 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm B -126.25 77.03 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10 ppm 200 190 180 170 160 150 140 130 120 110 100 90 80 TO LL <-50.00 70 60 50 40 30 20 10 ppm 45.06 30.18 -26.45 22.36 --0.00 45.07 7.5 1.93 2.05 -30.24 -22.36 C A 7 8 5 ° 4 3 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 ppm 9 8 5 4 3 ཡི་ OH 10 2 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 5 4 3 2 that th 7 I 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 115 2.21 4.00 1.0 ppm 6.96 2.76 5.01 1.0 ppm 6.30 1.00

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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