53E - Organic Chemistry (Mcmurry)

Question

Propose a structure for a compound ${\mathbf{C}}_{\mathbf{6}}{\mathbf{H}}_{\mathbf{12}}{\mathbf{O}}_{\mathbf{2}}$ that dissolves in dilute NaOH and shows the following ¹H NMR spectrum: 1.08 $\mathbf{\delta }$(9H, singlet), 2.2 $\mathbf{\delta }$(2H, singlet), and 11.2 $\mathbf{\delta }$(1H, singlet).

Step-by-Step Solution

Answer

A compound C₆H₁₂O₂ that dissolves in dilute NaOH and satisfies the spectral data is 3, 3-dimethylbutanoic acid and the structure is

Step 1: Definition of compounds

Any substance composed of identical molecules consisting of atoms of two or more chemical elements is defined as chemical compound.

Step 2: Explanations

The compound is a carboxylic acid as it has to oxygen atom and dissolves in NaOH The molecular formula of the ketone is C₆H₁₂O₂ Ignoring oxygen the molecular formula of the parent compound becomes C₆H₁₄ The compound has lesser hydrogen atom than the parent 

A compound C₆H₁₂O₂ that dissolves in dilute NaOH and satisfies the spectral data is 3, 3-dimethylbutanoic acid and the structure is