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H H;C, CH3 H3C- -CH3 OAc НОАС NEN -SO3 H H;C- N=N• SO3 CH3 proton transfer H3C -SO; H3C H Helianthin (red) NaOH H3C N=N- -SO;Na H3C Methyl orange

H H;C, CH3 H3C- -CH3 OAc НОАС NEN -SO3 H H;C- N=N• SO3 CH3 proton transfer H3C -SO; H3C H Helianthin (red) NaOH H3C N=N- -SO;Na H3C Methyl orange

Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Synthesis of Methyl Orange 

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### Methyl Orange Synthesis and Structure **Reaction Pathway:** 1. **Dimethylaniline Acetate Equilibrium:** - Initial structure: Aniline derivative with a dimethylammonium ion and acetate counterion (OAc⁻). - Equilibrium is established with dimethylaniline and acetic acid (HOAc). 2. **Azo Compound Formation:** - Reaction with a diazonium salt leading to the formation of an azo linkage (-N=N-) between the benzene ring structures. 3. **Proton Transfer:** - The azo compound undergoes a proton transfer, which creates a resonance-stabilized structure with emphasis on different electron locations and charges. 4. **Formation of Helianthin (Red Form):** - Protonated form of the azo compound is referred to as Helianthin, which appears red. 5. **Final Conversion to Methyl Orange:** - With the addition of sodium hydroxide (NaOH), deprotonation occurs, culminating in Methyl Orange, showing the final azo compound with a sodium sulfonate group (SO₃Na). **Explanation of Diagrams and Equilibrium:** - **Equilibrium Arrows:** Indicates reversible reactions where equilibrium exists between reactants and products. - **Structural Changes:** Transition between protonated and non-protonated forms is highlighted to show the behavior of azo compounds under different pH conditions, indicating acidity or alkalinity influences. - **Functional Group Identification:** - **Dimethylamino Group (N(CH₃)₂):** Present in dimethylaniline derivatives. - **Azo Linkage (-N=N-):** Integral to azodyes like Methyl Orange which gives it characteristic color properties. - **Sulfonate Group (SO₃⁻):** Contributes to solubility and ionic nature of the dye, impacting interactions within solutions. ### Educational Context: Methyl Orange is used as a pH indicator in titrations due to its color change properties. It is a synthetic dye falling under the azodyes category and its synthesis and structural transformations exemplify fundamental principles in organic chemistry, including equilibrium, resonance, and acid-base behavior in organic compounds.
Transcribed Image Text:### Methyl Orange Synthesis and Structure **Reaction Pathway:** 1. **Dimethylaniline Acetate Equilibrium:** - Initial structure: Aniline derivative with a dimethylammonium ion and acetate counterion (OAc⁻). - Equilibrium is established with dimethylaniline and acetic acid (HOAc). 2. **Azo Compound Formation:** - Reaction with a diazonium salt leading to the formation of an azo linkage (-N=N-) between the benzene ring structures. 3. **Proton Transfer:** - The azo compound undergoes a proton transfer, which creates a resonance-stabilized structure with emphasis on different electron locations and charges. 4. **Formation of Helianthin (Red Form):** - Protonated form of the azo compound is referred to as Helianthin, which appears red. 5. **Final Conversion to Methyl Orange:** - With the addition of sodium hydroxide (NaOH), deprotonation occurs, culminating in Methyl Orange, showing the final azo compound with a sodium sulfonate group (SO₃Na). **Explanation of Diagrams and Equilibrium:** - **Equilibrium Arrows:** Indicates reversible reactions where equilibrium exists between reactants and products. - **Structural Changes:** Transition between protonated and non-protonated forms is highlighted to show the behavior of azo compounds under different pH conditions, indicating acidity or alkalinity influences. - **Functional Group Identification:** - **Dimethylamino Group (N(CH₃)₂):** Present in dimethylaniline derivatives. - **Azo Linkage (-N=N-):** Integral to azodyes like Methyl Orange which gives it characteristic color properties. - **Sulfonate Group (SO₃⁻):** Contributes to solubility and ionic nature of the dye, impacting interactions within solutions. ### Educational Context: Methyl Orange is used as a pH indicator in titrations due to its color change properties. It is a synthetic dye falling under the azodyes category and its synthesis and structural transformations exemplify fundamental principles in organic chemistry, including equilibrium, resonance, and acid-base behavior in organic compounds.
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