Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 17, Problem 17.36P
Pentalene, azulene, and heptalene are conjugated hydrocarbons that do not contain a benzene ring. Which hydrocarbons are especially stable or unstable based on the number of
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Ethanol, 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.
(c) There is one (1) other positional isomer of X missing for reaction II. Draw the structural formula of this isomer.
Compounds with two carbonyl groups are named as alkane diones, for example:
R
2,3-butanedione
The compound above is an artificial flavor added to microwave popcorn and movie-theater popcorn to simulate the butter flavor.
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cyclohexane-1,3-dione
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Chapter 17 Solutions
Organic Chemistry
Ch. 17 - Prob. 17.1PCh. 17 - What orbitals are used to form the bonds indicated...Ch. 17 - Give the IUPAC name for each compound.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 - How many 13C NMR signals does each compound...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 - Prob. 17.16PCh. 17 - Problem 17.16 Rank the following compounds in...Ch. 17 - Problem 17.17 Draw the seven resonance structures...Ch. 17 - Prob. 17.19PCh. 17 - Prob. 17.20PCh. 17 - Prob. 17.21PCh. 17 - Prob. 17.22PCh. 17 - Problem 17.22 How many NMR signals does ...Ch. 17 - 17.23 Name each compound and state how many lines...Ch. 17 - Prob. 17.25PCh. 17 - Prob. 17.26PCh. 17 - Prob. 17.27PCh. 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. 17.31PCh. 17 - Prob. 17.32PCh. 17 - Prob. 17.33PCh. 17 - 17.33 Label each compound as aromatic,...Ch. 17 - Prob. 17.35PCh. 17 - 17.35 Pentalene, azulene, and heptalene are...Ch. 17 - 17.36 The purine heterocycle occurs commonly in...Ch. 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 - 17.61 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. 17.63PCh. 17 - 17.65 Use the observed data to decide whether C...Ch. 17 - Prob. 17.65PCh. 17 - Prob. 17.66PCh. 17 - Prob. 17.67PCh. 17 - 17.69 Although benzene itself absorbs at in its ...
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- Is it possible for a motor fuel to have a negative octane rating? Explain.arrow_forward1. Although there is only one alkene with the formula C2H4 (ethene) and only one with the formula C3H6 (propene), there are several alkenes with the formula C4H8. Draw all of the possible bond line structures for alkenes with the formula C4H3 including all possible structural and stereoisomers.arrow_forwardEGO He suggested that the bonds present in between any two carbon atoms in benzene can be either double or single bond. Lewis Huckel Michael Faraday OAugust Kekulé This bicyclic alkanes share two nonadjacent carbon atoms and one or more carbon atoms between them. O spirocyclic compounds O bridged rings fused rings O crown ethers This is one way of naming a benzene compound when two substituents are attached in a 1.2 positions of the ring. O ortho meta para Obetaarrow_forward
- Pyrethrins, such as jasmolin II (shown below), are a group of natural compounds that are synthesized by flowers of the genus Chrysanthemum (known as pyrethrum flowers) to act as insecticides. CH3 CH2=CH-CH. CH-C- -HCS 0-CH, CH,-C H2C- ČH, Which is not a functional group or structural feature in jasmolin II? cycloalkane carboxylic acid ester alkenearrow_forwardMatch each hydrocarbon with its associated structure (shown in different forms). Pentane - C5H12 Octane- C8H18arrow_forwardDescribe (meaning what you would do and observe) simple (not including melting points, boiling points, cleaving reactions, or instrumental analysis) chemical tests (if any) that would distinguish between the compounds named below. [Hing: using a table may be helpful] • 1-hexyne • cyclopentene • 2-methylbutane • 2-methyl-2-propanolarrow_forward
- Chemistry 2.) Draw the condensed structures (NOT line structures) for the following reactions of alcohols. CH3 a.) H3C- [H'] CH2-CH- CH3 CH3 H3C-CH-CH3 b.) H;C-CH2-CH-CH2 CH2-OH [0]arrow_forwardAs you can see from Table 11.4, each CH2 group added to the carbon chain of an alkane increases its boiling point. This increase is greater going from CH4 to C2H6 and from C2H6 to C3H8 than it is going from C8H18 to C9H20 or from C9H20 to C10H22. What do you think is the reason for this differencearrow_forwardWrite the balanced chemical equation for the complete combustion of ethane. Reactants Products C2H6 (g) + → Formulate (skeletal formula) the main products for the oxidation and dehydration reactions of the following compound: Reactant Oxidation product Dehydration products | OH CH3―CH2―CH―CH2―CH3arrow_forward
- Organic compounds may have characteristic odors as well as other characteristic physical properties. For example, the distinct odor of the seashore at low tide results in part from the presence of dimethyl sulfide (CH3SCH3), a molecule with a similar structure to dimethyl ether (CH3OCH3). Ethanethiol (CH3CH2SH), also called mercaptan, is an isomer of dimethyl sulfide with a much less pleasant odor.The table lists four related compounds and their enthalpies of vaporization (ΔH°vap) in kJ/mol. Compound ΔH°vap (kJ/mol) CH3OCH3 23 CH3SCH3 28 CH3CH2SH 27.5 CH3CH2OH 42 Rank the following compounds in order of increasing strength of their intermolecular forces, given the ΔH°vap listed for each. Place the compound with the strongest intermolecular forces (IMFs) at the top of the list. (Strongest to weaknest). Why is ΔHºvap for CH3SCH3 greater than ΔHºvap for CH3OCH3? A. CH3OCH3 is more polar. B. CH3SCH3 has stronger dipole–dipole attractions. C. CH3OCH3 can form…arrow_forwardThree components of the sex pheromone of the female sand bee (Ophrys sphegodes) are saturated hydrocarbons containing 23, 25, and 27 carbon atoms. How many H atoms does each of these alkanes contain? Interestingly, the early spider orchid emits a similar hydrocarbon mixture to attract male sand bees to pollinate its flowers.arrow_forwardFatty acids are molecules with a carboxylic acid on one end and long hydrocarbon chain on the other. The sodium salts of fatty acids (such as sodium strearate, shown below) are commonly used in soaps to trap nonpolar dirt and grease particles. Soap does not work well in "hard water, which is water with high concentration of magensium and calcium ions (often found in water obtained from wells) Explain this observation at a molecular level.arrow_forward
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