/*! This file is auto-generated */ .wp-block-button__link{color:#fff;background-color:#32373c;border-radius:9999px;box-shadow:none;text-decoration:none;padding:calc(.667em + 2px) calc(1.333em + 2px);font-size:1.125em}.wp-block-file__button{background:#32373c;color:#fff;text-decoration:none} Problem 25 Spectroscopic data for three com... [FREE SOLUTION] | 91影视

91影视

Spectroscopic data for three compounds with the molecular formula \(\mathrm{C}_{5} \mathrm{H}_{8}\) are given below; \(\mathrm{m}\) denotes a complex multiplet. Assign a structure to each compound. (Hint: One is acyclic; the others each contain one ring.) (a) IR \(910,1000,1650,3100 \mathrm{~cm}^{-1} ;{ }^{1} \mathrm{H}\) NMR \(\delta=2.79(\mathrm{t}, J=8 \mathrm{~Hz})\), 4.8-6.2 (m) ppm, integrated intensity ratio of the signals \(=1: 3\). (b) IR \(900,995,1650,3050 \mathrm{~cm}^{-1}\); \({ }^{1} \mathrm{H}\) NMR \(\delta=0.5 1.5(\mathrm{~m}), 4.8-6.0(\mathrm{~m}) \mathrm{ppm}\), integrated intensity ratio of the signals \(=5: 3\). (c) IR \(1611,3065 \mathrm{~cm}^{-1} ;{ }^{1} \mathrm{H}\) NMR \(\delta=1.5-2.5(\mathrm{~m}), 5.7(\mathrm{~m}) \mathrm{ppm}\), integrated intensity ratio of the signals \(=3: 1\). Is there more than one possibility?

Short Answer

Expert verified
Compound (a) is 1,3-pentadiene, compound (b) is 1-methylcyclopentene, and compound (c) is cyclopentadiene.

Step by step solution

01

Analyze the IR Spectrum for Compound (a)

The IR spectrum has peaks at 910, 1000, 1650, and 3100 cm鈦宦. These peaks indicate the presence of a terminal alkene (C-H stretch at 3100 cm鈦宦, C=C stretch at 1650 cm鈦宦, and C-H bending at 910 and 1000 cm鈦宦).
02

Analyze the 鹿H NMR Spectrum for Compound (a)

The NMR spectrum shows peaks at 未 = 2.79 ppm (triplet, J = 8 Hz) and 4.8-6.2 ppm (multiplet). An integrated intensity ratio of 1:3 suggests one hydrogen in the triplet and three hydrogens in the multiplet. This pattern is consistent with a terminal alkyne or conjugated diene system.
03

Assign a Structure to Compound (a)

Given the IR and NMR data, compound (a) is likely a conjugated diene. An example structure is 1,3-pentadiene.
04

Analyze the IR Spectrum for Compound (b)

The IR spectrum shows peaks at 900, 995, 1650, and 3050 cm鈦宦, indicating the presence of an alkene (C=C stretch at 1650 cm鈦宦 and C-H stretch at 3050 cm鈦宦).
05

Analyze the 鹿H NMR Spectrum for Compound (b)

The NMR spectrum shows peaks at 未 = 0.5-1.5 ppm (multiplet) and 4.8-6.0 ppm (multiplet) with an integrated intensity ratio of 5:3. This suggests an alkene with non-equivalent hydrogen environments.
06

Assign a Structure to Compound (b)

Given the IR and NMR data, compound (b) likely contains a cyclopentene ring. An example structure is 1-methylcyclopentene.
07

Analyze the IR Spectrum for Compound (c)

The IR spectrum shows peaks at 1611 and 3065 cm鈦宦, indicating the presence of an aromatic ring (C=C stretch at 1611 cm鈦宦 and C-H stretch at 3065 cm鈦宦).
08

Analyze the 鹿H NMR Spectrum for Compound (c)

The NMR spectrum shows peaks at 未 = 1.5-2.5 ppm (multiplet) and 5.7 ppm (multiplet) with an integrated intensity ratio of 3:1. This suggests the presence of an aromatic ring with substituents.
09

Assign a Structure to Compound (c)

Given the IR and NMR data, compound (c) likely contains a cyclopentadiene ring. An example structure is cyclopentadiene.
10

Determine if There Are More Than One Possibility

The assigned structures (1,3-pentadiene, 1-methylcyclopentene, and cyclopentadiene) are consistent with the provided spectroscopic data. Alternative structures may exist, but these assignments are reasonable based on the given data.

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Over 30 million students worldwide already upgrade their learning with 91影视!

Key Concepts

These are the key concepts you need to understand to accurately answer the question.

IR spectrum interpretation
The IR (Infrared) spectroscopy helps in identifying functional groups within a molecule by measuring the vibrations of bonds, which occur at specific wavelengths. In the exercise, let's break down the interpretation for compound (a). The peaks at **910, 1000, 1650, and 3100 cm鈦宦** serve as our clues. The peak at **3100 cm鈦宦** indicates a C-H stretch belonging to an alkene. Similarly, the **1650 cm鈦宦** peak signals the C=C stretch characteristic of alkenes. The bands at **910 and 1000 cm鈦宦** belong to the bending vibrations of C-H bonds typically seen in terminal alkenes. This suggests the presence of an unsaturated bond, like a double bond (C=C), in compound (a). For compound (b), very similar IR peaks indicate another alkene presence, while compound (c) indicates an aromatic ring due to the sharp peak at **1611 cm鈦宦**.
NMR spectrum interpretation
NMR (Nuclear Magnetic Resonance) spectroscopy provides information about the hydrogen atoms (protons) in a compound. For **compound (a)**, the peaks at 未 = **2.79 ppm** (triplet) and **4.8-6.2 ppm** (multiplet) are important, and the integrated intensity ratio of **1:3** suggests different hydrogen environments. The triplet at **2.79 ppm** indicates a set of three nearby hydrogens (J = 8 Hz), suggesting connectivity in a common structural motif, such as in a terminal alkyne or conjugated diene.

**Compound (b)**, has peaks at 未 = **0.5-1.5 ppm** (multiplet) and **4.8-6.0 ppm** (multiplet) with an intensity ratio of **5:3**. The wide range indicates hydrogens in various chemical environments, typical of a ring structure with alkene characteristics, like in a cyclopentene.

For **compound (c)**, peaks at 未 = **1.5-2.5 ppm** (multiplet) and **5.7 ppm** (multiplet) with a **3:1** ratio are observed. The peaks are consistent with an aromatic structure with hydrogen substituents, similar to those seen in cyclopentadiene, confirming the presence of aromaticity.
molecular structure determination
Determining the molecular structure involves integrating data from both IR and NMR spectra. For **compound (a)**, combining the IR and NMR analysis, we deduced a conjugated diene structure, specifically **1,3-pentadiene**. The IR data indicated a terminal alkene, and the NMR confirmed it with the observed coupling patterns and integration ratio.

**Compound (b)** was assigned as **1-methylcyclopentene**. The IR spectrum suggesting an alkene and the NMR data indicating a structure with nonequivalent hydrogen environments led to this conclusion. Additionally, the hint indicating that the compound is cyclic further assisted in narrowing down this structure.

**Compound (c)**, with an aromatic ring indicated by the IR spectrum, together with the NMR spectrum showing a peak pattern typical for aromatic hydrogens, resulted in the assignment of **cyclopentadiene** as the structure. The 3:1 integration ratio of protons and their 未 values correlated well with this structure. By piecing together spectroscopic clues, we can accurately determine molecular structures for these compounds.

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

The molecular formulas and \({ }^{13} \mathrm{C}\) NMR data (in ppm) for several compounds are given here. The type of carbon, as revealed from DEPT spectra, is specified in each case. Deduce a structure for each compound. (a) \(\mathrm{C}_{4} \mathrm{H}_{6}: 30.2\left(\mathrm{CH}_{2}\right), 136.0(\mathrm{CH}) ;\) (b) \(\mathrm{C}_{4} \mathrm{H}_{6} \mathrm{O}: 18.2\left(\mathrm{CH}_{3}\right), 134.9(\mathrm{CH}), 153.7(\mathrm{CH})\), \(193.4(\mathrm{CH}) ;(\mathrm{c}) \mathrm{C}_{4} \mathrm{H}_{8}: 13.6\left(\mathrm{CH}_{3}\right), 25.8\left(\mathrm{CH}_{2}\right), 112.1\left(\mathrm{CH}_{2}\right), 139.0(\mathrm{CH}) ;(\mathrm{d}) \mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O}: 17.6\left(\mathrm{CH}_{3}\right)\) \(25.4\left(\mathrm{CH}_{3}\right), 58.8\left(\mathrm{CH}_{2}\right), 125.7(\mathrm{CH}), 133.7\left(\mathrm{C}_{\text {quatemary }}\right) ;(\mathrm{e}) \mathrm{C}_{5} \mathrm{H}_{8}: 15.8\left(\mathrm{CH}_{2}\right), 31.1\left(\mathrm{CH}_{2}\right), 103.9\left(\mathrm{CH}_{2}\right)\) \(149.2\left(\mathrm{C}_{\text {quaternary }}\right) ;\) (f) \(\mathrm{C}_{7} \mathrm{H}_{10}: 25.2\left(\mathrm{CH}_{2}\right), 41.9(\mathrm{CH}), 48.5\left(\mathrm{CH}_{2}\right), 135.2(\mathrm{CH}) .\) (Hint: This one is difficult. The molecule has one double bond. How many rings must it have?)

What is the degree of unsaturation in cyclobutane? (a) Zero; (b) one; (c) two; (d) three

Draw the structures of the following molecules: (a) trans-3-penten-1-ol; (b) 2-cyclohexen-1-ol.

Convert each of the following IR frequencies into micrometers. (a) \(1720 \mathrm{~cm}^{-1}(\mathrm{C}=\mathrm{O})\) (b) \(1650 \mathrm{~cm}^{-1}(\mathrm{C}=\mathrm{C})\) (c) \(3300 \mathrm{~cm}^{-1}(\mathrm{O}-\mathrm{H})\) (d) \(890 \mathrm{~cm}^{-1}\) (alkene bend) (e) \(1100 \mathrm{~cm}^{-1}(\mathrm{C}-\mathrm{O})\) (f) \(2260 \mathrm{~cm}^{-1}(\mathrm{C} \equiv \mathrm{N})\)

Draw the structures of each of the following compounds, rank them in order of acidity, and circle the most acidic hydrogen(s) in each: cyclopentane, cyclopentanol, cyclopentene, 3-cyclopenten-1-ol.

See all solutions

Recommended explanations on Chemistry Textbooks

View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.