Explanations 
Textbooks 
Flashcards 
91影视 AI 
Notes 
Study Plans 
Study Sets 
Find a degree 
Magazine Chapter 14: Q56P (page 527)
Treatment of 2-methylpropanenitrile \(\left( {{{\left( {{\bf{C}}{{\bf{H}}_{\bf{3}}}} \right)}_{\bf{2}}}{\bf{CHCN}}} \right)\) with\({\bf{C}}{{\bf{H}}_{\bf{3}}}{\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{MgBr}}\), followed by aqueous acid, affords compound V, which has molecular formula \({{\bf{C}}_{\bf{7}}}{{\bf{H}}_{{\bf{14}}}}{\bf{O}}\). V has a strong absorption in its IR spectrum at 1713 \({\rm{c}}{{\rm{m}}^{{\rm{ - 1}}}}\), and gives the following 1 H NMR data: 0.91 (triplet, 3 H), 1.09 (doublet, 6 H), 1.6 (multiplet, 2 H), 2.43 (triplet, 2 H), and 2.60 (septet, 1 H) ppm. What is the structure of V? We will learn about this reaction in Chapter 22.
Short Answer
Step by step solution
IR spectroscopy
The IR spectroscopy is used to determine the structure by the change in the dipole momentof the compound (stretching and bending). It gives the signals of ketone as 1740\({\rm{c}}{{\rm{m}}^{{\rm{ - 1}}}}\).
This stretching frequency decreases with the electron donor groups.
Degree of unsaturation
The structure of the molecule is determined by the degree of unsaturation, if present in the given molecule. It is calculated by the following formula:
\({\rm{Degree}}\,{\rm{of}}\,{\rm{unsaturation}} = {{\rm{C}}_{\rm{n}}}{\rm{ - }}\frac{{\rm{H}}}{{\rm{2}}}{\rm{ - }}\frac{{\rm{X}}}{{\rm{2}}}{\rm{ + }}\frac{{\rm{N}}}{{\rm{2}}}{\rm{ + 1}}\)
Here, X is the number of the halogen atoms.
Explanation
IR absorption at 1713\({\rm{c}}{{\rm{m}}^{{\rm{ - 1}}}}\): C=O
NMR data: 0.91 (triplet, 3 H or \({\rm{C}}{{\rm{H}}_{\rm{3}}}\) group), 1.09 (doublet, 6 H or 2\({\rm{C}}{{\rm{H}}_{\rm{3}}}\)), 1.6 (multiplet, 2 H or \({\rm{C}}{{\rm{H}}_2}\)), 2.43 (triplet, 2 H or \({\rm{C}}{{\rm{H}}_2}\)), and 2.60 (septet, 1 H) ppm
Over 30 million students worldwide already upgrade their learning with 91影视!
