Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 13, Problem 13.61P
Explain why a
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Why do aldehydes, esters, and amides all have a strong absorption in the
1630-1780 cm1 region of their IR spectra?
A) The bond between H and the sp³-hybridized C in these functional groups
vibrates in this energy range.
B) Each of these functional groups has at least two resonance structures, and
the different vibrations of the resonance structures give off energy in this
region.
C) The bond between O and the sp²-hybridized C in these functional groups
vibrates at a frequency in this energy range.
D) Light at this wavenumber causes the average C to O bond length to increase
which causes more of this light to be transmitted.
E) An electron in the bond of these functional groups gets excited to the *
orbital.
The beer-lambert law is A = εlc, where A is the absorbance, ε is the molar extinction coefficient, l is the path lengh in cm and C is the concentration. The beer lambert law can be expressed in the form of y=mx + b, where A is y, and C is x.What is b and how is it used to calculate the final absorbance?
Explain why a ketone carbonyl typically absorbs at a lower wavenumber than an aldehyde carbonyl (1715 vs. 1730 cm−1).
Chapter 13 Solutions
Organic Chemistry
Ch. 13 - What is the mass of the molecular ion formed from...Ch. 13 - Prob. 13.2PCh. 13 - Use the following information to propose a...Ch. 13 - Prob. 13.4PCh. 13 - What molecular ions would you expect for the...Ch. 13 - The mass spectrum of 2,3-dimethylpentane also...Ch. 13 - The base peak in the mass spectrum of 2, 2,...Ch. 13 - (a) What mass spectral fragments are formed by ...Ch. 13 - What cations are formed in the mass spectrometer...Ch. 13 - The low-resolution mass spectrum of an unknown...
Ch. 13 - Benzene, toluene, and p-xylene BTX are often added...Ch. 13 - Prob. 13.12PCh. 13 - Prob. 13.13PCh. 13 - Prob. 13.14PCh. 13 - Prob. 13.15PCh. 13 - How do the IR spectra of the isomers cyclopentane...Ch. 13 - Problem 13.17 How do the three isomers of...Ch. 13 - Problem 13.18 What functional groups are...Ch. 13 - Problem-13.19 What are the major IR absorptions in...Ch. 13 - Problem-13.20 What are the major IR absorptions in...Ch. 13 - Problem-13.21 Which of the following possible...Ch. 13 - Problem-13.22 Propose structures consistent with...Ch. 13 - 13.23 What major IR absorptions are present above ...Ch. 13 - Problem-13.24 The mass spectrum of the following...Ch. 13 - Prob. 13.25PCh. 13 - Which compound gives a molecular ion at m/z= 122,...Ch. 13 - Propose two molecular formulas for each molecular...Ch. 13 - Propose four possible structures for a hydrocarbon...Ch. 13 - Problem-13.29 What is the molecular formula for...Ch. 13 - Problem-13.30 Propose a molecular formula for rose...Ch. 13 - 13.31 Match each structure to its mass spectrum
Ch. 13 - 13.32 Propose two possible structures for a...Ch. 13 - 13.33 What cations are formed in the mass...Ch. 13 - 13.34 and have the same molecular ion in the...Ch. 13 - 13.35 For each compound, assign likely...Ch. 13 - Prob. 13.36PCh. 13 - 13.37 Propose a structure consistent with each...Ch. 13 - 13.38 A low-resolution mass spectrum of the...Ch. 13 - 13.39 Primary alcohols often show a peak in their...Ch. 13 - 13.40 Like alcohols, ethers undergo α cleavage by...Ch. 13 - 13.41 Which of the highlighted bonds absorbs at...Ch. 13 - 13.42 What major IR absorptions are present above ...Ch. 13 - 13.43 How would each of the following pairs of...Ch. 13 - 13.44 Morphine, heroin, and oxycodone are three...Ch. 13 - 13.45 Reduction of cyclohex-2-enone can yield...Ch. 13 - Prob. 13.46PCh. 13 - 13.47 Match each compound to its IR spectrum
Ch. 13 - 13.48 Propose possible structures consistent with...Ch. 13 - A chiral hydrocarbon X exhibits a molecular ion at...Ch. 13 - 13.50 A chiral compound has a strong absorption...Ch. 13 - 13.51 Treatment of benzoic acid with followed by...Ch. 13 - 13.52 Treatment of benzaldehyde with in aqueous ...Ch. 13 - Prob. 13.53PCh. 13 - 13.54 Reaction of 2-methylpropanoic acid with ...Ch. 13 - 13.55 Reaction of pentanoyl chloride with lithium...Ch. 13 - Prob. 13.56PCh. 13 - 13.57 Treatment of anisole with and forms P,...Ch. 13 - 13.58 Reaction of with forms compound ,...Ch. 13 - Problem-13.59 The carbonyl absorption of an amide...Ch. 13 - Prob. 13.60PCh. 13 - Problem-13.61 Explain why a ketone carbonyl...Ch. 13 - 13.62 Oxidation of citronellol, a constituent of...
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- What would be the frequency of the fundamental absorption of a hydroxyl group if its first overtone was observed at 6200 cm³¹? What is the energy possessed by a band that appeared at 1710 cm¹ in an IR spectrum?arrow_forwardWhat characteristics of the methyl benzoate spectrum rule out an aldehyde or carboxylicacid functional group giving the absorption at 1723 cm-1?arrow_forwardA student takes an IR spectrum of an unknown compound. The IR spectrum shows significant stretches at 3159 cm³¹ (m, sh), 3089 cm ¹ (m, sh), 3000 cm ¹ (m, sh), 2997 cm-¹ (m, sh), 1620 cm-¹ (s, sh), 1494 cm-¹ (s, sh), and 1210 cm-¹ (s, sh). Which possible compound is it? Key: S = Strong, M = Medium, W = Weak, Sh = Sharp, Br = Broad Anisole Aniline O Acetanilide O Acetone O Phenolarrow_forward
- N-H bonds absorb IR radiation at very similar frequencies as O-H (alcohol) bonds. Oftentimes, they are not quite as large. Why?arrow_forward3. Identify C-Cl stretching peaks in CDC13 and CHC13 spectra. Do these peaks have exactly the same frequencies for both compounds? Explain your answer. 4. Is the C==O stretching frequency the same for acetone and deuterated acetone? Explain your answer. 5. Identify C==O overtone in acetone spectrum which corresponds to the transition from ground level, n=0, to the second excited level, n=2.arrow_forwardWhat 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)arrow_forward
- Carbon monoxide [CO] exhibits an IR absorption at 2143cm-1, acetone [CH3C(O)CH3],exhibits an IR absorption for the CO vibration at 1715 cm-1 and ethanol [CH3CH2OH] exhibits an IR absorption for CO at ~1150 cm-1. Draw Lewis structures of these three molecules and use your structures to explain the observed differences in the CO IR absorption peak frequency (nCO).arrow_forward12 of 15 The range of IR absorption of C=O stretching vibrations (including ketones, aldehydes, carboxylic acids, esters, acyl halides, anhydrides and amides) is: 2260-2240 cm1 -1 1740-1690 cm" 1650-1550 cm1 1850-1550 cm1arrow_forwardwhat is the wavenumber (cm-1) and Type of bond/functional group represented herearrow_forward
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