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

1. Predict the organic product(s) of the following reactions. Assume excess of reagents unless otherwise noted. a) &l BH3 •THF b) 1) NaOH 2) H3O+ solve d) ala 1) EtMgBr 2) H3O+ e) H2N سكر CuLi NH2 1) SOCI2 2) EtMgBr 3) H3O+ NC H3O+ Δ

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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