Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 2, Problem 4LGP
Consider the molecular formula
Predict approximate frequencies for IR absorptions that could be used to distinguish the four compounds representing these
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A student has acquired an IR spectra of an unknown six-carbon molecule and has determined that it is either 2-hexyne, 1-
hexyne, or 1-hexene. How can the student use their knowledge of IR spectroscopy to determine the identity of the molecule? In
your answer, clearly specify what regions of the IR spectrum the student should look at and what bonds are responsible for the
absorption bands you indicate.
What IR frequencies would enable a chemist to
distinguish between these molecules?
CH;CH2OH and CH;CH2OCH;CH3
and
CH,
HCHCHCCIICH CH, d
3000-3100 cm-1 (=C-H)| 1620-1680 cm-1 (C=C)
3200-3400 cm-1 (OH) || 3000-3100 cm-1 (=C-H)
How can you distinguish aldehydes, ketones, and carboxylic acids from each other using IR spectra? Explain using specific examples.
Chapter 2 Solutions
Organic Chemistry
Ch. 2 - Practice Problem 2.1
Propose structures for two...Ch. 2 - Prob. 2PPCh. 2 - Prob. 3PPCh. 2 - Prob. 4PPCh. 2 - Prob. 5PPCh. 2 - Practice Problem 2.6
Using a three-dimensional...Ch. 2 - Practice Problem 2.7
Trichloromethane (, also...Ch. 2 - Prob. 8PPCh. 2 - Prob. 9PPCh. 2 - Practice Problem 2.10
Write bond-line structural...
Ch. 2 - Practice Problem 2.11 Although we shall discuss...Ch. 2 - Practice Problem 2.12 Write bond-line structural...Ch. 2 - Prob. 13PPCh. 2 - Practice Problem 2.14
One way of naming ethers is...Ch. 2 - Practice Problem 2.15 Eugenol is the main...Ch. 2 - Practice Problem 2.16
One way of naming amines is...Ch. 2 - Practice Problem 2.17 Which amines in Practice...Ch. 2 - Prob. 18PPCh. 2 - Prob. 19PPCh. 2 - Practice Problem 2.20
Write bond-line formulas for...Ch. 2 - Practice Problem 2.21
Write bond-line formulas for...Ch. 2 - Practice Problem 2.22
Write bond-line formulas for...Ch. 2 - Prob. 23PPCh. 2 - Practice Problem 2.24 Write another resonance...Ch. 2 - Prob. 25PPCh. 2 - Practice Problem 2.26
Which compound would you...Ch. 2 - Practice Problem 2.27 Arrange the following...Ch. 2 - Prob. 28PPCh. 2 - Prob. 29PCh. 2 - Identify all of the functional groups in each of...Ch. 2 - 2.31 There are four alkyl bromides with the...Ch. 2 - Prob. 32PCh. 2 - Classify the following alcohols as primary,...Ch. 2 - 2.34 Classify the following amines as primary,...Ch. 2 - Prob. 35PCh. 2 - Identify all of the functional groups in Crixivan,...Ch. 2 - 2.37 Identify all of the functional groups in...Ch. 2 - 2.38 (a) Indicate the hydrophobic and hydrophilic...Ch. 2 - Hydrogen fluoride has a dipole moment of 1.83 D;...Ch. 2 - 2.40 Why does one expect the cis isomer of an...Ch. 2 - Prob. 41PCh. 2 - Prob. 42PCh. 2 - Prob. 43PCh. 2 - 2.44 Consider each of the following molecules in...Ch. 2 - True or false: For a molecule to be polar, the...Ch. 2 - 2.46 Which compound in each of the following...Ch. 2 - Prob. 47PCh. 2 - The IR spectrum of propanoic acid (Fig. 2.16)...Ch. 2 - Prob. 49PCh. 2 - Write structural formulas for four compounds with...Ch. 2 - There are four amides with the formula C3H7NO. (a)...Ch. 2 - Prob. 52PCh. 2 - Prob. 53PCh. 2 - Prob. 54PCh. 2 - Prob. 55PCh. 2 - 2.56 Compound C is asymmetric, has molecular...Ch. 2 - 2.57 Examine the diagram showing an -helical...Ch. 2 - Prob. 1LGPCh. 2 - Prob. 2LGPCh. 2 - Prob. 3LGPCh. 2 - Consider the molecular formula C4H8O2. Predict...Ch. 2 - Consider the molecular formula C4H8O2. If any of...Ch. 2 - Prob. 6LGPCh. 2 - Consider the molecular formula.
7. Pick five...Ch. 2 - Prob. 8LGP
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11.57 Draw the cis and trans isomers for each of the following: (11.6)
a. 2-pentene
b. 3-hexene
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- Indicate the functional groups present in the IR spectra shown below (you may choose more than one answer): choices: N-H group C≡N group Alkene (C=C) group C=O group Aromatic ring group O-H group Alkyne (C≡C) grouparrow_forwardExplain why this is the correct spectra for these molecules. Identify a specific absorption band which identifies each characteristic functional group of the chosen molecule.arrow_forwardN-H bonds absorb IR radiation at very similar frequencies as O-H (alcohol) bonds. Oftentimes, they are not quite as large. Why?arrow_forward
- The infrared absorbtion of the N-H stretch in amines occurs approximately at a wavelength of 2.9 x 10-6 m. What is the approximate vibrational force constant, k, of N-H bond? Note: you can assume the reduced mass is equal to the mass of the H atom (which is reasonable since it's attached to a much heavier atom). 48.0 kg/s? 1.20 x 102 kg/s2 7.0 x 102 kg/s2 4.2 x 10-1 kg/s? 1.3 x 103 kg/s?arrow_forwardExplain why these are the correct spectra for the molecules. Identify a specific absorption band which identifies each characteristic functional group of the molecule chosen.arrow_forwardThe NMR spectrum of a compound can reveal whether the atoms within the molecule are equivalent or different. For example, the hydrogen atoms in CH2=CH2 are equivalent: they all exist in an identical environment. However, in CH2=CHCI, the two hydrogen atoms attached to the same carbon atom are equivalent, but different from the hydrogen atom on the other carbon atom. Predict how many different types of hydrogen atoms can be identified in the 1H NMR spectrum of each of the following molecules: (а) C2H2 (b) cis-C2H2C12 (c) trans-C2H2Cl2 (d) CH3OH In the molecule C2H5C1, the hydrogen atoms would all be different if the (e) molecule existed in only one conformation. However, only two types of hydrogen atoms are detected. Propose an explanation.arrow_forward
- The IR spectra of nonane (C,H20) and 1-hexanol (C,H13OH) are shown below. Assign each spectrum to the correct compound and identify the frequencies and the functional groups used to support your assignment. λ (μη) 6 7 8 9 10 11 12 1314 15 2.5 100 3 5 20 4 90 80 70 60 50 40 30 20 10 4000 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 Frequency (cm¬') A (µm) 2.5 100 8 9 10 11 12 13 14 15 3 4 5 7 20 90 80 70 60 50 40 30 20 10 4000 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 600 400 Frequency (cm¬!) (%) Transmission (%) Transmissionarrow_forwardWhy is this the correct spectra for these molecules. Identify a specific absorption band which identifies each characteristic functional group of the molecule chosen.arrow_forwardThe organic compound 1,4-dimethylbenzene (also known as p-xylene) has the formula (CH3)2C6H4. Its structure has two CH3 (methyl) groups substituted at opposite positions on the benzene (C6H6) ring. Predict the number of peaks in the low-resolution proton NMR spectrum of this compound and the relative areas of the peaks.arrow_forward
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