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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

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Step by step solution

01

IR-spectroscopy

Each organic functional group has a characteristic IR- absorption frequency. Based on that, the structure of the compound can be deduced.

02

Subpart (a)

The given spectrum indicates a broad peak at3400cm-1,-2500cm-1 and confirms the presence of 鈥揙H group with C-H stretching.

A peak at1710cm-1 represents the C=O stretch in carboxylic acid.

A peak at 1660cm-1represents C=C stretching.

From this data, it is clear that the given compound has the below shown structural formula:

Structure (a)

03

Subpart (b)

The given spectrum indicates the characteristic peak . This represents the C-H stretch.

A characteristic peak at1710cm-1 represents the C=O stretch.

Hence, the structure of the compound is as shown below:

Structure (b)

04

 Step 3: Subpart (b)

The given spectrum indicates the characteristic peak 3000cm-1-2840cm-1. This represents the C-H stretch.

A characteristic peak at1710cm-1 represents the C=O stretch.

Hence, the structure of the compound is as shown below:

Structure (b)

05

Subpart (c)

The peak at2900cm-1 represents the presence of C-H stretch.

The peak at 2260cm-1represents stretch.

The peak The peaks between 1600cm-1-1400cm-1represents the C=C stretch in benzene.

Hence, the structure of the compound that represents the given IR spectrum is shown below:

Structure (c)

06

Subpart (d)

A characteristic broad IR peak 3500cm-1-3300cm-1is observed .It represents the presence of O-H group.

A peak between 3000cm-1-2800cm-1represents the C-H stretch.

The peaks between1600cm-1-1400cm-1 represents the C=C stretch in benzene.

Hence, the structure of the compounds for the given IR spectrum is as shown below:

Structure (d)

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Most popular questions from this chapter

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, 鈥淚t looks like an alkane.鈥 But it seemed too reactive to be an alkane, so she did a GC鈥揗S. 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: (a) Use the mass spectrum to propose a molecular formula. How many elements of unsaturation are there? (b) Use the IR spectrum to determine the functional group(s), if any. (c) Propose one or more structures for this compound. What parts of the structure are uncertain? If you knew that hydrogenation of the compound gives n-octane, would the structure still be uncertain? (d) Propose structures for the major fragments at 39, 67, 81, and 95 in the mass spectrum.

Question: Which of the bonds shown in red are expected to have IR-active stretching frequencies?

Question: A common lab experiment is the dehydration of cyclopentanol tocyclopentene.

a. Explain how you could tell from the IR spectrum whether your product was pure cyclopentene, pure cyclopentanol or a mixture of cyclopentene and cyclopentanol. Give approximate frequencies for distinctive peaks.

b. Explain why mass spectrometry might not be a good way to distinguish cyclopentene from cyclopentanol.

Predict the characteristic infrared absorptions of the functional groups in the following molecules.

(a) cyclopentene

(b) hexan-2-ol

(c) hexan-2-one

(d) hex-1-yne

(e) dimethylamine

(f) hexanoic acid

(g) hexanenitrile

(h) methyl acetate

(i) hexanamide.

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