The structure of the product on the basis of mass spectra, IR and NMR data is to be determined. Concept introduction: Hydrogenolysis reaction of benzyl alcohols results in the cleavage of the benzyl and oxygen bond. It may also involve group migration, which is usually carried out by the phenyl ring. Infrared absorption bands indicate the functional groups present in a compound. For example, carbonyl group shows a band from 1600 to 1750 cm -1 , hydroxyl group shows a band from 3400 to 35 50 cm -1 . So, if a compound shows a band in the carbonyl range only, it is an aldehyde or ketone , while if it shows one in the region of hydroxyl, it is an alcohol or a phenol. If two bands are observed with one in each region, it is a carboxylic acid . NMR data indicates the number and types of protons or carbons present in a compound based on the number of signals obtained in 1 H NMR or 13 C NMR, respectively. 1 H NMR signals are often with multiplicity such as doublets and triplets, which indicates the number of protons present on the carbons adjacent to that proton. The protons of an aromatic ring show a signal from 6.5 – 7.5 ppm , those of alkyl group from 0.5 to 1.5 ppm while alkyl groups adjacent to a carbonyl group or oxygen atom show signals from 2.0 to 3.0 ppm . Alcohol group shows a signal from 2.0 to 3.0 ppm but is always a singlet. The mass spectra of a compound indicate the molecular ion peak, which give the molecular mass of the compound.

Question

Want to see the full answer?

Answer 1

Question

Chapter 16, Problem 57P

Interpretation Introduction

Interpretation:

The structure of the product on the basis of mass spectra, IR and NMR data is to be determined.

Concept introduction:

Hydrogenolysis reaction of benzyl alcohols results in the cleavage of the benzyl and oxygen bond. It may also involve group migration, which is usually carried out by the phenyl ring.

Infrared absorption bands indicate the functional groups present in a compound. For example, carbonyl group shows a band from 1600 to 1750 cm-1, hydroxyl group shows a band from 3400 to 3550 cm-1. So, if a compound shows a band in the carbonyl range only, it is an aldehyde or ketone, while if it shows one in the region of hydroxyl, it is an alcohol or a phenol. If two bands are observed with one in each region, it is a carboxylic acid.

NMR data indicates the number and types of protons or carbons present in a compound based on the number of signals obtained in 1H NMR or 13C NMR, respectively. 1H NMR signals are often with multiplicity such as doublets and triplets, which indicates the number of protons present on the carbons adjacent to that proton. The protons of an aromatic ring show a signal from 6.5–7.5 ppm, those of alkyl group from 0.5 to 1.5 ppm while alkyl groups adjacent to a carbonyl group or oxygen atom show signals from 2.0 to 3.0 ppm. Alcohol group shows a signal from 2.0 to 3.0 ppm but is always a singlet.

The mass spectra of a compound indicate the molecular ion peak, which give the molecular mass of the compound.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

d) Determine the formal charge on the nitrogen atom in each of the structures. NH3 NH2 N C бобкат : N N H H Н H2N-OH A B C D E F G

Lewis Structure, Hybridization & Molecular Geometry a) Draw the Lewis Structure of the molecules; Label the hybridization of each carbon atom; Predict the approximate molecular geometry around each carbon atom. CH3CHO CH3CN b) Draw the Lewis Structure of Nitromethane; Predict the approximate molecular geometry around the nitrogen atom. CH3NO2 c) Draw the Lewis Structure; Label the hybridization of the boron atom; Predict the approximate molecular geometry. BF3 BF4

a. The structure of the bicarbonate (hydrogen carbonate) ion, HCO3-, HCO3 " is best described as a hybrid of several contributing resonance forms, two of which are shown here. HO :0: HO + :Ö: Bicarbonate is crucial for the control of body pH (for example, blood pH 7.4). A more self-indulgent use is in baking soda, where it serves as a source of CO2 CO2 gas, which gives bread and pastry their fluffy constituency. (i) Draw at least one additional resonance form. = (ii) Using curved "electron-pushing" arrows, show how these Lewis structures may be interconverted by movement of electron pairs. (iii) Determine which form or forms will be the major contributor(s) to the real structure of bicarbonate, explaining your answer on the basis of the criteria in Section 1-5.