ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 17, Problem 17.65P
Use the observed
aromatic. C shows
signals at
extent?
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Use the observed 1H NMR data to decide whether C and its dianion are aromatic, antiaromatic, or not aromatic. C shows NMR signals at –4.25 (6 H) and 8.14–8.67 (10 H) ppm. The dianion of C shows NMR signals at –3 (10 H) and 21 (6 H) ppm. Why are the signals shifted upeld (or downeld) to such a large extent?
Based on its 13C NMR spectrum, how many types of nonequivalent carbons exist in benzonitrile and how many different types of aromatic (benzene) carbons can be seen in 13C NMR of benzonitrile?
Based on the structures given below, which of the following statements is entirely true?
Quinoline
NH
Isoquinoline Indole
Isoindole
All four compounds are non-aromatic, with 12 pi-electrons each and are equal in basicity.
Only quinoline and Isoquinoline having 10 pi-electrons each are aromatic while indole and isoindole are antiaromatic having 8 pi-electrons each
The nitrogen atoms of quinoline and isoquinoline are sp2 hybridized while the nitrogen atoms of indole and isoindole are sp³ hybridized.
All four compounds are aromatic, with 10 pi-electrons each and are equal in basicity.
All four compounds are aromatic, with 10 pi-electrons each, and with quinoline and isoquinoline being stronger bases than indole and isoind
Chapter 17 Solutions
ORGANIC CHEMISTRY
Ch. 17 - Prob. 17.1PCh. 17 - Problem 17.2 What orbitals are used to form the...Ch. 17 - Problem-17.3. Give the IUPAC name for each...Ch. 17 - Prob. 17.4PCh. 17 - Problem-17.5 What is the structure of propofol,...Ch. 17 - Problem 17.6 What is the structure of a compound...Ch. 17 - Problem 17.7 How many NMR signals does each...Ch. 17 - Prob. 17.8PCh. 17 - Prob. 17.9PCh. 17 - Prob. 17.10P
Ch. 17 - Prob. 17.11PCh. 17 - Prob. 17.12PCh. 17 - Prob. 17.13PCh. 17 - Problem 17.14 Januvia, the trade name for...Ch. 17 - Prob. 17.15PCh. 17 - Problem 17.16 Rank the following compounds in...Ch. 17 - Problem 17.17 Draw the seven resonance structures...Ch. 17 - Prob. 17.18PCh. 17 - Prob. 17.19PCh. 17 - Prob. 17.20PCh. 17 - Prob. 17.21PCh. 17 - Problem 17.22 How many NMR signals does ...Ch. 17 - 17.23 Name each compound and state how many lines...Ch. 17 - Prob. 17.24PCh. 17 - Prob. 17.25PCh. 17 - Prob. 17.26PCh. 17 - 17.27 Give the IUPAC name for each compounds.
a....Ch. 17 - 17.28 Draw a structure corresponding to each...Ch. 17 - 17.29 a. Draw the 14 constitutional isomers of...Ch. 17 - Prob. 17.30PCh. 17 - Prob. 17.31PCh. 17 - Prob. 17.32PCh. 17 - 17.33 Label each compound as aromatic,...Ch. 17 - Prob. 17.34PCh. 17 - 17.35 Pentalene, azulene, and heptalene are...Ch. 17 - 17.36 The purine heterocycle occurs commonly in...Ch. 17 - Prob. 17.37PCh. 17 - 17.38
How many electrons does C contain?
How...Ch. 17 - Prob. 17.39PCh. 17 - 17.40 Explain the observed rate of reactivity of...Ch. 17 - 17.41 Draw a stepwise mechanism for the following...Ch. 17 - Prob. 17.42PCh. 17 - 17.43 Draw additional resonance structures for...Ch. 17 - Prob. 17.44PCh. 17 - Prob. 17.45PCh. 17 - 17.46 Which compound in each pair is the stronger...Ch. 17 - 17.47 Treatment of indene with forms its...Ch. 17 - Prob. 17.48PCh. 17 - 17.49 Draw the conjugate bases of pyrrole and...Ch. 17 - 17.50 a. Explain why protonation of pyrrole occurs...Ch. 17 - Prob. 17.51PCh. 17 - Prob. 17.52PCh. 17 - 17.53 How many signals does each compound...Ch. 17 - 17.54 Which of the diethylbenzene isomers (ortho,...Ch. 17 - 17.55 Propose a structure consistent with each...Ch. 17 - 17.56 Propose a structure consistent with each...Ch. 17 - 17.57 Thymol (molecular formula ) is the major...Ch. 17 - 17.58 You have a sample of a compound of molecular...Ch. 17 - 17.59 Explain why tetrahydrofuran has a higher...Ch. 17 - 17.60 Rizatriptan (trade name Maxalt) is a...Ch. 17 - 17.61 Zolpidem (trade name Ambien) promotes the...Ch. 17 - 17.62 Answer the following questions about...Ch. 17 - 17.63 Stanozolol is an anabolic steroid that...Ch. 17 - Prob. 17.64PCh. 17 - 17.65 Use the observed data to decide whether C...Ch. 17 - Prob. 17.66PCh. 17 - Prob. 17.67PCh. 17 - Prob. 17.68PCh. 17 - 17.69 Although benzene itself absorbs at in its ...
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- The 'H NMR spectrum of compound A (C3H100) has four signals: a multiplet at 8 = 7.25-7.32 ppm (5 H), a singlet at d = 5.17 ppm (1 H), a quartet at d = 4.98 ppm (1 H), and a doublet at ô = 1.49 ppm (3 H). There are 6 signals in its 13C NMR spectrum. The IR spectrum has a broad absorption in the -3200 cm-1 region. Compound A reacts with KMNO4 in a basic solution followed by acidification to give compound B with the molecular formula C7H6O2. Draw structures for compounds A and B.arrow_forwardAll-cis cyclodecapentaene is a stable molecule that shows a single absorption in its1HNMR spectrum at 5.67 δ. Tell whether it is aromatic, and explain its NMR spectrumarrow_forwardBased on the structures given below, which of the following statements is entirely true? N Quinoline NH Isoquinoline Indole Isoindole All four compounds are non-aromatic, with 12 pi-electrons each and are equal in basicity. All four compounds are aromatic, with 10 pi-electrons each and are equal in basicity. Only quinoline and isoquinoline having 10 pi-electrons each are aromatic while indole and isoindole are antiaromatic having 8 pi-electrons each. All four compounds are aromatic, with 10 pi-electrons each, and with quinoline and isoquinoline being stronger bases than indole and isoindole. The nitrogen atoms of quinoline and isoquinoline are sp2 hybridized while the nitrogen atoms of indole and isoindole are sp³ hybridized Previousarrow_forward
- Explain why the carbonyl carbon of an aldehyde or ketone absorbs farther downeld than the carbonyl carbon of an ester in a 13C NMR spectrum.arrow_forwardPropose a structural formula for each compound consistent with its 1H-NMR and 13C-NMR spectra.arrow_forwardWhen compound A (C5H12O) is treated with HBr, it forms compound B (C5H11Br). The 1H NMR spectrum of compound A has a 1H singlet, a 3Hdoublet, a 6H doublet, and two 1H multiplets. The 1H NMR spectrum of compound B has a 6H singlet, a 3H triplet, and a 2H quartet. Identifycompounds A and B.arrow_forward
- Propose a structural formula for each compound consistent with its 1H-NMR and 13C-NMR spectra.arrow_forwardExplain why the carbonyl carbon of an aldehyde or ketone absorbs farther downfield than the carbonyl carbon of an ester in a 13C NMR spectrum.arrow_forwardPropose a structural formula for each compound consistent with its 1H-NMR and 13C-NMR spectra.arrow_forward
- Select the most accurate statement about the following compound. The compound is aromatic because there are 4n+2 pi electrons. O The compound is aromatic because it is completely conjugated throughout the entire ring. O The compound is non-aromatic (not aromatic) because it is not planar. O The compound is anti-aromatic because there are 4n pi electrons.arrow_forwardis what i chose the correct answer to the queshtionarrow_forwardCompound P has molecular formula C5H9ClO2. Deduce the structure of P from its 1H and 13C NMR spectra.arrow_forward
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