A structure for the alcohol with molecular formula C 9 H 12 O and the following spectral data is to be proposed. 1HNMR: 0.88 δ (triplet,Rel.area=3.00); 1.80 δ (quintet, Rel.area=2.00); 2.32 δ (Rel.area=1.00); 4.54 δ (triplet, Rel.area=1.00); 7.24 δ (Rel.area=5.00). Concept introduction: In 1HNMR spectrum, the alcoholic proton absorption occurs in the range 3.4 δ - 4.5 δ while that of phenolic proton occur in the range 3.0 to 8.0. The aromatic protons give a broad peak in the range 6.5 δ - 8.0 δ, the benzylic protons normally absorb in the region 2.3 δ - 3.0 δ. The absorption due to 1 0 alkyl group (CH 3 ) is seen around 0.7 δ - 1.3 δ, that due to a 2 0 alkyl group (CH 2 ) is seen around 1.2 δ - 1.6 δ while that due to 3 0 alkyl group (CH) is seen around 1.4 δ - 1.8 δ The multiplicity of a signal gives an idea about the protons present in the adjacent carbons. To propose: A structure for the alcohol with molecular formula C 9 H 12 O and the following spectral data is to be proposed. 1HNMR: 0.88 δ (triplet,Rel.area=3.00); 1.80 δ (quintet, Rel.area=2.00); 2.32 δ (Rel.area=1.00); 4.54 δ (triplet, Rel.area=1.00); 7.24 δ (Rel.area=5.00).

Question

For this question, if the product is racemic, input both enantiomers in the same Marvin editor. A) Input the number that corresponds to the reagent which when added to (E)-but-2-ene will result in a racemic product. Input 1 for Cl, in the cold and dark Input 2 for Oy followed by H₂O, Zn Input 3 for D₂ with metal catalyst Input 4 for H₂ with metal catalyst B) Draw the skeletal structure of the major organic product made from the reagent in part A Marvin JS Help Edit drawing C) Draw the skeletal structure of the major organic product formed when (2)-but-2-ene is treated with peroxyacetic acid. Marvin 35 Help

Answer 1

Question

Chapter 17.SE, Problem 74AP

Interpretation Introduction

Interpretation:

A structure for the alcohol with molecular formula C₉H₁₂O and the following spectral data is to be proposed.

1HNMR: 0.88 δ (triplet,Rel.area=3.00); 1.80 δ (quintet, Rel.area=2.00); 2.32 δ (Rel.area=1.00); 4.54 δ (triplet, Rel.area=1.00); 7.24 δ (Rel.area=5.00).

Concept introduction:

In 1HNMR spectrum, the alcoholic proton absorption occurs in the range 3.4 δ - 4.5 δ while that of phenolic proton occur in the range 3.0 to 8.0. The aromatic protons give a broad peak in the range 6.5 δ - 8.0 δ, the benzylic protons normally absorb in the region 2.3 δ - 3.0 δ.

The absorption due to 1⁰ alkyl group (CH₃) is seen around 0.7 δ - 1.3 δ, that due to a 2⁰ alkyl group (CH₂) is seen around 1.2 δ - 1.6 δ while that due to 3⁰ alkyl group (CH) is seen around 1.4 δ - 1.8 δ The multiplicity of a signal gives an idea about the protons present in the adjacent carbons.

To propose:

A structure for the alcohol with molecular formula C₉H₁₂O and the following spectral data is to be proposed.

1HNMR: 0.88 δ (triplet,Rel.area=3.00); 1.80 δ (quintet, Rel.area=2.00); 2.32 δ (Rel.area=1.00); 4.54 δ (triplet, Rel.area=1.00); 7.24 δ (Rel.area=5.00).

Interpretation Introduction

b)

C₈H₁₀O₂

Interpretation:

A structure for the alcohol with molecular formula C₈H₁₀O₂ and the following spectral data is to be proposed.

IR: 3500 cm^-1,

1HNMR: 2.60 δ (Rel.area=1.00); 3.76 δ (Rel.area=3.00); 4.53 δ (Rel.area=2.00); 6.85 δ (Rel.area=2.00); 7.23 δ (Rel.area=2.00).

Concept introduction:

In 1HNMR spectrum, the alcoholic proton absorption occurs in the range 3.4 δ - 4.5 δ while that of phenolic proton occur in the range 3.0 to 8.0. The aromatic protons give a broad peak in the range 6.5 δ - 8.0 δ, the benzylic protons normally absorb in the region 2.3 δ - 3.0 δ.

To propose:

A structure for the alcohol with molecular formula C₈H₁₀O₂ and the following spectral data is to be proposed.

1HNMR: 2.60 δ (Rel.area=1.00); 3.76 δ (Rel.area=3.00); 4.53 δ (Rel.area=2.00); 6.85 δ (Rel.area=2.00); 7.23 δ (Rel.area=2.00).

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