ORGANIC CHEMISTRY
6th Edition
ISBN: 9781266633973
Author: SMITH
Publisher: MCG
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Chapter 15, Problem 22P
Interpretation Introduction
Interpretation: All the
Concept introduction: A molecule must be cyclic, planar, completely conjugated and should follow
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Aromatic compounds got their name because many have
strong smells. Benzene, toluene, aniline, and phenol are
common structures from which most aromatic
compounds are derived. (Figure 1) When naming
aromatic compounds with three or more substituents, the
ring is numbered to give the smallest possible set of
numbers. For example, this phenol derivative (Figure 2)
is called 4-bromo-3-chlorophenol. The substituents
Figure
CH3
NH₂
1 of 2 >
OH
benzene toluene aniline phenol
Name the following molecule by its IUPAC name.
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Part B
Name the following molecule by its IUPAC name.
CI
Br
CH3
CI
Br
What is the total number of π electrons?
What is the number of delocalized π ring electrons?
Draw the line bond structures for the following alkenes, cyclic alkenes, and alkynes:
Can you explain to me about this part A) noncyclic alkenes that contain 4 carbon atoms (3 possible), please?
Can you explain to me about this part B) cyclic alkenes that contain 4 carbon atoms (4 possible), please?
Can you explain to me about this part C) alkynes that contain 4 carbon atoms (2 possible, neither of them is a cyclic alkyne), please?
Chapter 15 Solutions
ORGANIC CHEMISTRY
Ch. 15.2 - Prob. 1PCh. 15.2 - Problem 17.2 What orbitals are used to form the...Ch. 15.3 - Prob. 4PCh. 15.3 - Problem-17.5 What is the structure of propofol,...Ch. 15.6 - Prob. 7PCh. 15.8 - Prob. 8PCh. 15.8 - Prob. 11PCh. 15.8 - Prob. 12PCh. 15.8 - Problem 17.16 Rank the following compounds in...Ch. 15.8 - Problem 17.17 Draw the seven resonance structures...
Ch. 15 - 17.23 Name each compound and state how many lines...Ch. 15 - Prob. 21PCh. 15 - Prob. 22PCh. 15 - 17.27 Give the IUPAC name for each compounds.
a....Ch. 15 - 17.28 Draw a structure corresponding to each...Ch. 15 - 17.29 a. Draw the 14 constitutional isomers of...Ch. 15 - Prob. 26PCh. 15 - Prob. 27PCh. 15 - 17.38
How many electrons does C contain?
How...Ch. 15 - Prob. 36PCh. 15 - 17.40 Explain the observed rate of reactivity of...Ch. 15 - 17.41 Draw a stepwise mechanism for the following...Ch. 15 - Prob. 39PCh. 15 - 17.43 Draw additional resonance structures for...Ch. 15 - Prob. 41PCh. 15 - Prob. 42PCh. 15 - 17.46 Which compound in each pair is the stronger...Ch. 15 - 17.47 Treatment of indene with forms its...Ch. 15 - Prob. 45PCh. 15 - 17.49 Draw the conjugate bases of pyrrole and...Ch. 15 - 17.50 a. Explain why protonation of pyrrole occurs...Ch. 15 - Prob. 48PCh. 15 - Prob. 49PCh. 15 - 17.53 How many signals does each compound...Ch. 15 - 17.54 Which of the diethylbenzene isomers (ortho,...Ch. 15 - 17.55 Propose a structure consistent with each...Ch. 15 - 17.56 Propose a structure consistent with each...Ch. 15 - 17.57 Thymol (molecular formula ) is the major...Ch. 15 - 17.58 You have a sample of a compound of molecular...Ch. 15 - 17.59 Explain why tetrahydrofuran has a higher...Ch. 15 - 17.60 Rizatriptan (trade name Maxalt) is a...Ch. 15 - 17.61 Zolpidem (trade name Ambien) promotes the...Ch. 15 - 17.62 Answer the following questions about...Ch. 15 - 17.63 Stanozolol is an anabolic steroid that...Ch. 15 - Prob. 61P
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- What are aromatic hydrocarbons? Benzene exhibits resonance. Explain. What are the bond angles in benzene? Give a detailed description of the bonding in benzene. The electrons in benzene are delocalized, while the electrons in simple alkenes and alkynes are localized. Explain the difference.arrow_forwardIs it possible for a motor fuel to have a negative octane rating? Explain.arrow_forwardMeta directors in electrophilic aromatic substitution reactions have A) unpaired electrons in the atom attached to the ring B) partial or full positive charge on the atom attached to the ring C) highly electronegative atoms attached to the ring an so or sp2 hybridized atom attached to the ringarrow_forward
- One possible isomer created by a substitution reaction that replaces a hydrogen atom attached to the aromatic ring of toluene with a chlorine atom is shown here. Draw two other possible isomers in which the chlorine atom replaces a different hydrogen atom attached to the aromatic ring:arrow_forward12) What is the major difference between an antiaromatic and aromatic compound? A) The structure must be cyclic for aromatic but not antiaromatic compounds? B) Antiaromatic compounds have at least one sp3 hybridized atom in the ring C) Antiaromatic compounds can assume a chair-like structure while aromatic compounds are nearly flat D) Aromatic compounds cannot have a charged atom in the structure E) Only aromatic compounds follow Huckle's rule.arrow_forwardDraw and name all aromatic compounds with the formula C7H7Clarrow_forward
- In a laboratory experiment, one sherbet lemon sweet produced 6.00 mL of carbon dioxide. d) Calculate the minimum mass (g) of tartaric acid necessary to produce this 6.00 mL volume of carbon dioxide. (Assume that 1 mole of carbon dioxide occupies 24.0 L at room temperature and pressure). e) By making the appropriate substitutions for tartaric acid's H (hydrogen) and OH (hydroxyl) groups among positions A, B, D and E in the structure shown below, how many different stereoisomers of tartaric acid are possible? HO₂C B CO₂H A Earrow_forwardGive an example of a 3,4-unsaturated aldehyde molecule with a total of 16 carbons, with at least one aromatic group and one alkyl group. Name this example you gave according to the IUPAC system.arrow_forwardAnswer this question:How to draw the line bond formula or lewis structure of a methyl ketone with the chemical formula C6H5C3H5O? (also taking into consideration the solubility test and chemical test results provided below) Based on the results of the solubility tests the compound is insoluble in water, 10% NaOH and 10% HCl but soluble in concentrated H2SO4. The functional group/class is identified to be Methyl Ketone, based on the results of the chemical tests on Table 2. CHEMICAL TEST OBSERVATIONS +(compound tested positive for the chemical reaction)/ otherwise (-) Molisch test turbid colorless solution - 2,4-DNP test formation of orange-yellow precipitates + Tollen’s test turbid colorless solution - Ninhydrin test clear pale-yellow solution - iodoform test clear pale-yellow solution +arrow_forward
- Determine if the following compounds are aromatic, non-aromatic, or anti-aromatic. Show a structure that helps to support your classification. This structure should not just redraw the compound; show lone pairs, resonance, and/or contributing π bonds as part of your explanation.arrow_forwardHow come the structure labeled as 1 has 8 pi electrons? If the double bond has 2 pi electrons, and you count the lone pairs, wouldn't it have 6 pi electrons? Why does the structure labeled as 2 has aromaticity? If the pi bond has 2 pi electrons and then you coun the lone pairs, wouldn't it only have 5 pi electrons?arrow_forwardEthanol, C2H5OH, and propane, C3H8, have approximately the same molar mass, yet ethanol has a much higher boiling point. Briefly explain why. Ethanol, C2H5OH, and dimethyl ether, CH3OCH3, have the same molar mass, yet ethanol has a much higher boiling point. Briefly explain why. Write an equation to show the reaction between ethanol, C2H5OH and methyllithium, CH3Li. Draw all non-bonding electrons and show electron flow with curved arrows. 37. Write an equation that shows the reaction between acetic acid (CH3COOH) and triethylamine (CH3CH2)3N. Draw all non-bonding lone electron pairs and show the electron flow with curved arrows.arrow_forward
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