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The following NMR spectra correspond to the compound of formula (A) C9H10O2, (B) C4H6O2, C6H10O2 . Propose structure, and show how it is consistent with the observed absorptions.

Short Answer

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(a) The organic compound can be identified by studying magnetic behavior. This technique is nuclear magnetic resonance spectroscopy or NMR spectroscopy.

This method helps us to find the structure and molecular formula of any organic compound.

Step by step solution

01

About NMR spectra

(a) The organic compound can be identified by studying magnetic behavior. This technique is nuclear magnetic resonance spectroscopy or NMR spectroscopy.

This method helps us to find the structure and molecular formula of any organic compound.

02

About the given spectra

The given compound A has the chemical shift values 11.8 ppm, 7.3 ppm, 3.8 ppm, and 1.5 ppm. The given compound bears 5 elements of unsaturation. The hydrogen sets are 1H, 5H, 1H, and 3H.

03

About the structure

The chemical shift value of 11.8 ppm with 1H corresponds to the COOH group. The chemical shift value of 7.3 ppm with 5H corresponds to the mono-substituted benzene ring.

The chemical shift value 3.8 ppm with 1H with quartet corresponds to the CHCH3group. The chemical shift value 1.5 ppm with 3H with doublet corresponds to the CHCH3 group. Thus, the chemical structure of compound A is:

04

About the given spectra

(b) The given compound B has the chemical shift values 12.1 ppm, 6.2 ppm, 5.7 ppm, and 1.9 ppm. The given compound bears 2 elements of unsaturation. The hydrogen sets are 1H, 1H, 1H, and 3H.

05

About the structure

The chemical shift value of 12.1 ppm with 1H corresponds to the COOH group. The chemical shift value 6.2 ppm with 1H corresponds to the H-C=C and it is a singlet. The chemical shift value 5.7 ppm with 1H with singlet corresponds to the H-C=C.

The chemical shift value 1.9 ppm with 3H with singlet corresponds to the vinyl CH3 group. Thus, the chemical structure of compound B is:

06

About the given spectra

(c) The given compound C has the chemical shift values 12.15 ppm, 7.1 ppm, 5.8 ppm, and 2.2-0.9 ppm. The given compound bears 2 elements of unsaturation. The hydrogen sets are 1H, 1H, and 1H.

07

About the structure

The chemical shift value of 12.15 ppm with 1H corresponds to the COOH group. The chemical shift value 7.1 ppm with 1H corresponds to the H-C=C-COOH and it is a multiplet.

The chemical shift value 5.8 ppm with 1H with doublet corresponds to the C=C(H)COOH. The chemical shift value 2.2-0.9 ppm corresponds to the vinyl CH2CH2CH3 group. Thus, the chemical structure of compound C is:

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Most popular questions from this chapter

Phosgene is the acid chloride of carbonic acid. Although phosgene was used as a war gas in World War I, it is now used as a reagent for the synthesis of many useful products. Phosgene reacts like other acid chlorides, but it can react twice.

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(b) Predict the products formed when phosgene reacts with 1 equivalent of ethanol, followed by 1 equivalent of aniline.

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Isobutyloxycarbonyl chloride

Predict the major products of the following reactions.

An unknown compound gives the NMR, IR, and mass spectra shown next. Propose a structure, and show how it is consistent with the observed absorptions. Show fragmentations that account for the prominent ion at m/z69 and the smaller peak at m/z99.

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(a) butane

(b) isobutane

(c) 2-methylbutane

(d) cyclohexane

(e) norbornane (bicyclo heptane)

Consider the following reaction-energy diagram.

(a) Label the reactants and the products. Label the activation energy for the first step and the second step.

(b) Is the overall reaction endothermic or exothermic? What is the sign of ?

(c) Which points in the curve correspond to intermediates? Which correspond to transition states?

(d) Label the transition state of the rate-limiting step. Does its structure resemble the reactants, the products, or an intermediate?

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