Q66E - Organic Chemistry (Mcmurry)

Question

Question: 21-66 Assign structures to compounds with the following ¹H N MR  spectra:

$$\begin{gathered} \left(a\right){\mathbf{C}}_{\mathbf{4}}\mathbf{ }{\mathbf{H}}_{\mathbf{7}}\mathbf{ }\mathbf{ClO} \\ \mathbf{IR}\mathbf{ }\mathbf{:}\mathbf{1810}\mathbf{ }{\mathbf{cm}}^{\mathbf{-}\mathbf{1}} \end{gathered}$$

$$\begin{gathered} \left(b\right){\mathbf{C}}_{\mathbf{6}\mathbf{ }}{\mathbf{H}}_{\mathbf{7}}\mathbf{ }{\mathbf{NO}}_{\mathbf{2}} \\ \mathbf{IR}\mathbf{:}\mathbf{2250}\mathbf{,}\mathbf{1735}\mathbf{ }{\mathbf{cm}}^{\mathbf{-}\mathbf{1}} \end{gathered}$$

Step-by-Step Solution

Answer

The structures to compounds with the following ¹H NMR spectra

  a) $C_4{H}_{7}ClO$

               

b) $C_5{H}_{7}N{O}_2$

           

Step 1: Introduction to the Concept

The arrangement of chemical bonds between atoms in a molecule (in anion or radical with many atoms), particularly which atoms are chemically bound to which other atoms with what kind of chemical bond, as well as any geometric shape information needed to uniquely identify the type of molecule.

Step 2: Solution Explanation

$$\begin{gathered} \left(\mathrm{a}\right) {\mathrm{C}}_4{\mathrm{H}}_7\mathrm{ClO} \\ \mathrm{IR} :1810{\mathrm{cm}}^{-1} \end{gathered}$$

The structure is depicted below,

Step 3: Solution Explanation

$$\begin{gathered} \left(b\right) C_5{H}_{7}N{O}_2 \\ IR\mathit{ }:2250,1735 c{m}^{-1} \end{gathered}$$

The structure is depicted below,