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For each hydrocarbon spectrum, determine whether the compound is an alkane, an alkene, an alkyne, or an aromatic hydrocarbon, and assign the major peaks above (to the left of) 1600 cm-1 . More than one unsaturated group may be present.

Short Answer

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Answer

The first spectrum represents alkenes.

The second spectrum represents alkanes.

The third spectrum represents aromatic hydrocarbon

Step by step solution

01

IR spectrum

The functional group present in a molecule can be determined by using its IR spectrum.

For the compounds with bond, the characteristic peak is observed at 1700cm-1 .

For alkanes, the characteristic stretch is observed at 3000cm-1 .

For alkenes the characteristic stretching peak is observed at 1500cm-1 .

02

First spectrum:Alkenes

A thin absorption at about 1700 cm-1is observed pointing downward. It is considered as carbonyl group (C=O). Alkenes (C=C) stretch is observed around 1500 cm-1. To be sure about alkene, there is unsaturated hydrocarbon at 3000 cm-1(C=C-H).

03

Second Spectrum:Alkanes

Alkanes have stretches at about 3000 cm-1 (C-H), C-H scissoring at about 1470 cm-1, methyl rock at about and long chain methyl rock at about.

04

Third Spectrum: Aromatic Hydrocarbon

Aromatic ring absorption spectra consist of series of bumps (1650 cm-1to 2000 cm-1). Number of bumps depends upon substitution of benzene ring.

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Most popular questions from this chapter

Show the fragmentations that give rise to the peaks at m/z 43, 57, and 85 in the mass spectrum of 2,4-dimethylpentane (Figure 12-17).

Question: A C-D (carbonโ€“deuterium) bond is electronically much like a C-H bond, and it has a similar stiffness, measured by the spring constant, k. The deuterium atom has twice the mass (m) of a hydrogen atom, however.

(a) The infrared absorption frequency is approximately proportional tokm , when one of the bonded atoms is much heavier than the other, and m is the lighter of the two atoms (H or D in this case). Use this relationship to calculate the IR absorption frequency of a typical C-D bond. Use as a typical C-H absorption frequency.

(b) A chemist dissolves a sample in deuterochloroform (CDCl3) and then decides to take the IR spectrum and simply evaporates most of theCDCl3 . What functional group will appear to be present in this IR spectrum as a result of theCDCl3 impurity?

Question: (Another true story.) A student who was checking into her lab desk found an unlabeled sample from a previous student. She was asked to identify the sample. She did an IR spectrum and declared, โ€œIt looks like an alkane.โ€ But it seemed too reactive to be an alkane, so she did a GCโ€“MS. The mass spectrum is shown next. Identify the compound as far as you can, and state what part of your identification is uncertain. Propose fragments corresponding to the numbered peaks.


Question: Four infrared spectra are shown, corresponding to four of the following compounds. For each spectrum, determine the structure and explain how the peaks in the spectrum correspond to the structure you have chosen

Question: (A true story.) While organizing the undergraduate stockroom, a new chemistry professor found a half-gallon jug containing a cloudy liquid (bp 100โ€“105 ยฐC), marked only โ€œSTUDENT PREP.โ€ She ran a quick mass spectrum, which is printed below. As soon as she saw the spectrum (without even checking the actual mass numbers), she said, โ€œI know what it is.โ€

(a) What compound is the โ€œstudent prepโ€? Any uncertainty in the structure?

(b) Suggest structures for the fragments at 136, 107, and 93. Why is the base peak (at m/z 57) so strong?

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