Nucleophilic Aromatic Substitution - Addition and Identification of an Amine

Steven W. Goldstein; Ashley Bill; Jyothi Dhuguru; Ola Ghoneim

doi:10.1021/acs.jchemed.6b00680

Nucleophilic Aromatic Substitution - Addition and Identification of an Amine

Steven W. Goldstein, Ashley Bill, Jyothi Dhuguru, Ola Ghoneim

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

Abstract

The addition of a nucleophilic functional group to an electron-deficient aromatic ring is a versatile reaction in the modern organic chemistry arsenal. The proper positioning of a leaving group on this ring effectively allows for a substitution reaction to occur. A 3 h laboratory experiment is described in which students utilize a common electrophilic aromatic ring and affect a substitution with an unknown amine, the identity of which is later characterized by the melting point and ¹H NMR spectrum of the product.

Original language	English (US)
Pages (from-to)	1388-1390
Number of pages	3
Journal	Journal of Chemical Education
Volume	94
Issue number	9
DOIs	https://doi.org/10.1021/acs.jchemed.6b00680
State	Published - Sep 12 2017
Externally published	Yes

Keywords

Addition Reactions
Amines/Ammonium Compounds
Aromatic Compounds
Nucleophilic Substitution
Organic Chemistry
Problem Solving/Decision Making
Second-Year Undergraduate

ASJC Scopus subject areas

General Chemistry
Education

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10.1021/acs.jchemed.6b00680

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title = "Nucleophilic Aromatic Substitution - Addition and Identification of an Amine",

abstract = "The addition of a nucleophilic functional group to an electron-deficient aromatic ring is a versatile reaction in the modern organic chemistry arsenal. The proper positioning of a leaving group on this ring effectively allows for a substitution reaction to occur. A 3 h laboratory experiment is described in which students utilize a common electrophilic aromatic ring and affect a substitution with an unknown amine, the identity of which is later characterized by the melting point and 1H NMR spectrum of the product.",

keywords = "Addition Reactions, Amines/Ammonium Compounds, Aromatic Compounds, Nucleophilic Substitution, Organic Chemistry, Problem Solving/Decision Making, Second-Year Undergraduate",

author = "Goldstein, {Steven W.} and Ashley Bill and Jyothi Dhuguru and Ola Ghoneim",

note = "Publisher Copyright: {\textcopyright} 2017 The American Chemical Society and Division of Chemical Education, Inc.",

year = "2017",

month = sep,

day = "12",

doi = "10.1021/acs.jchemed.6b00680",

language = "English (US)",

volume = "94",

pages = "1388--1390",

journal = "Journal of Chemical Education",

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T1 - Nucleophilic Aromatic Substitution - Addition and Identification of an Amine

AU - Goldstein, Steven W.

AU - Bill, Ashley

AU - Dhuguru, Jyothi

AU - Ghoneim, Ola

PY - 2017/9/12

Y1 - 2017/9/12

N2 - The addition of a nucleophilic functional group to an electron-deficient aromatic ring is a versatile reaction in the modern organic chemistry arsenal. The proper positioning of a leaving group on this ring effectively allows for a substitution reaction to occur. A 3 h laboratory experiment is described in which students utilize a common electrophilic aromatic ring and affect a substitution with an unknown amine, the identity of which is later characterized by the melting point and 1H NMR spectrum of the product.

AB - The addition of a nucleophilic functional group to an electron-deficient aromatic ring is a versatile reaction in the modern organic chemistry arsenal. The proper positioning of a leaving group on this ring effectively allows for a substitution reaction to occur. A 3 h laboratory experiment is described in which students utilize a common electrophilic aromatic ring and affect a substitution with an unknown amine, the identity of which is later characterized by the melting point and 1H NMR spectrum of the product.

KW - Addition Reactions

KW - Amines/Ammonium Compounds

KW - Aromatic Compounds

KW - Nucleophilic Substitution

KW - Organic Chemistry

KW - Problem Solving/Decision Making

KW - Second-Year Undergraduate

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DO - 10.1021/acs.jchemed.6b00680

M3 - Article

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SN - 0021-9584

VL - 94

SP - 1388

EP - 1390

JO - Journal of Chemical Education

JF - Journal of Chemical Education

IS - 9

ER -

Nucleophilic Aromatic Substitution - Addition and Identification of an Amine

Abstract

Keywords

ASJC Scopus subject areas

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