ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 17, Problem 17.68P
Interpretation Introduction
Interpretation: An explanation corresponding to the given statement that triphenylene resembles to benzene in that it does not undergo addition reaction with
Concept introduction: The delocalization of bond, lone pair, or free electrons from one place to another is known as resonance. The stability of compound depends upon the number of resonating structures. More the resonating structures of compound more will its stability.
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Vanillin, C8H8O3, is the active ingredient in vanilla flavoring. It contains a six-membered aromatic ring with an aldehyde group on carbon 1, an alkoxy group (ether) on carbon 3, and a hydroxyl group (alcohol) on carbon 4. Draw the structure of vanillin.
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• In cases where there is more than one answer, just draw one.
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ChemDoodle
a
You were tasked to propose a structure for a compound with a chemical formula of C₂H₂N. In
the laboratory, the compound appears as a clear, colorless liquid.
To determine the structure of the compound, you subject the compound to several solubility tests
and chemical tests. The observations for these tests are summarized:
SOLUBILITY GROUP: Group V
Insoluble in water and
10% NaOH but soluble in
10% HCI
FUNCTIONAL GROUP/CLASS: Amine
1) Based on the results of the solubility tests and chemical tests, what is the most probable
structure of C7H9N? Draw your answer in the box below. You may draw the compound
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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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- 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_forwardFormaldehyde, H2C=O, is known to all biologists because of its usefulness as a tissue preservative. When pure, formaldehyde trimerizes to give trioxane, C3H6O3, which, surprisingly enough, has no carbonyl groups. Only one monobromo derivative (C3H5BrO3) of trioxane is possible. Propose a structure for trioxane.arrow_forwardSodium hydride, NaH, is available commercially as a gray-white powder. It melts at 800°C with decomposition. It reacts explosively with water and ignites spontaneously upon standing in moist air. Q) Write an equation for the reaction between sodium hydride and 1-butyne, CH3CH2C = CH. Use curved arrows to show the flow of electrons in this reactionarrow_forward
- Compounds X and Y both have the formula C7H14. Both X and Y react with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2-methylhexane. The heat of hydrogenation of X is greater than that of Y. Both X and Y react with HCI to give the same single C₂H₁5Cl compound as the major product. What is the structure of X? • In cases where there is more than one answer, just draw one. 7 0▾ ChemDoodleⓇ 146arrow_forwardDraw the structure of the organic product formed from the reaction of sodium methoxide with 1‑chloro‑4‑nitrobenzene. Be sure to show formal charges.arrow_forwardButylated hydroxytoluene (BHT) is a common preservativeadded to cereals and other dry foods. Its systematic name is 1-hydroxy-2,6-di-tert-butyl-4-methylbenzene (where “tert-butyl”is 1,1-dimethylethyl). Draw the structure of BHT.arrow_forward
- Reaction of (CH3)3CH with Cl2 forms two products: (CH3)2CHCH2Cl (63%) and (CH3)3CCl (37%). Why is the major product formed by cleavage of the stronger 1° C–H bond?arrow_forwardGlucose, C6H12O6, contains an aldehyde group but exist predominantly in the form of the cyclic hemiacetal show below. A cyclic hemiacetal is formed when the —OH group of one carbon bonds to the carbonyl group of another carbon. Identify which carbon provides the —OH group and which provides the —CHO? Give a functional isomer of glucose and draw its structure.arrow_forward8) Compound A is composed of 87.4% carbon and 12.6% hydrogen and has a molar mass of 96.2 g/mol. Compound A reacts with water and sulfuric acid to produce Compound B. Compound B subsequently reacts with acidic potassium dichromate to produce a ketone. Which of the following could NOT be Compound A?: * A) 4-methxlexclohexens. B) 4-methyleyclopentene C) sxclopentyl ethene D) 1-methylcyclohexenearrow_forward
- b) An alkyl halide W has the molecular formula CaH,Br. One of the isomers , X can rotate plane-polarised light . Another isomer, Y is a primary alkyl halide that reacts with ethanolic potassium hydroxide to form alkene, Z which can reacts with ozone and zinc followed by hydrolysis to yield propanone and methanal. Identify the compounds X. Y and Z.arrow_forwardWrite the structure of the following compound: 2-(2-chlorophenyl)-1 -iodoethane.arrow_forwardPropene and benzene react with bromine, Br2, in absence of UV light in different ways. The reaction of propene is an addition reaction whereas that of benzene is a substitution reaction. Give the best explanation of this difference.arrow_forward
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