ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 1, Problem 1.69P
Two useful organic compounds that contain
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Two useful organic compounds that contain Cl atoms are vinyl chloride (CH2=CHCl) and chloroethane (CH3CH2Cl). Vinyl chloride is the starting material used to prepare poly(vinyl chloride), a plastic in insulation, pipes, and bottles. Chloroethane (ethyl chloride) is a local anesthetic. Why is the C–Cl bond in vinyl chloride stronger than the C–Cl bond in chloroethane?
Two useful organic compounds that contain Cl atoms are vinyl chloride(CH2=CHCl) and chloroethane (CH3CH2Cl). Vinyl chloride is the startingmaterial used to prepare poly(vinyl chloride), a plastic in insulation,pipes, and bottles. Chloroethane (ethyl chloride) is a local anesthetic.Why is the C–Cl bond in vinyl chloride stronger than the C–Cl bond inchloroethane?
A chemist wants to observe the following reaction:
2H2 + O2 → 2H2O
The chemist is standing inside a room with oxygen in the air and has a balloon filled with hydrogen. The chemist holds a small flame up to the hydrogen balloon. When the balloon pops, the hydrogen explodes in a ball of fire.
Based on what you know about breaking and forming bonds, explain which part of the reaction is higher in energy (i.e., does it take more energy to break the bonds of the reactants, or is more energy given off when the product bonds are formed?). Defend your answer in three to five sentences.
Chapter 1 Solutions
ORGANIC CHEMISTRY
Ch. 1 - While the most common isotope of nitrogen has a...Ch. 1 - Label each bond in the following compounds as...Ch. 1 - How many covalent bonds are predicted for each...Ch. 1 - Draw a valid Lewis structure for each species. a....Ch. 1 - Draw an acceptable Lewis structure for each...Ch. 1 - Prob. 1.6PCh. 1 - Draw a Lewis structure for each ion. a. CH3Ob....Ch. 1 - Prob. 1.8PCh. 1 - Draw Lewis structures for each molecular formula....Ch. 1 - Classify each pair of compounds as isomers or...
Ch. 1 - Prob. 1.11PCh. 1 - Prob. 1.12PCh. 1 - Prob. 1.13PCh. 1 - Draw a second resonance structure for each species...Ch. 1 - Prob. 1.15PCh. 1 - Prob. 1.16PCh. 1 - Prob. 1.17PCh. 1 - Prob. 1.18PCh. 1 - Using the principles of VSEPR theory, you can...Ch. 1 - Convert each condensed formula to a Lewis...Ch. 1 - Prob. 1.21PCh. 1 - Prob. 1.22PCh. 1 - Convert each skeletal structure to a complete...Ch. 1 - What is the molecular formula of quinine, the...Ch. 1 - Draw in all hydrogens and lone pairs on the...Ch. 1 - Prob. 1.26PCh. 1 - What orbitals are used to form each of the CC, and...Ch. 1 - What orbitals are used to form each bond in the...Ch. 1 - Determine the hybridization around the highlighted...Ch. 1 - The unmistakable odor of a freshly cut cucumber is...Ch. 1 - Prob. 1.31PCh. 1 - Rank the following atoms in order of increasing...Ch. 1 - Prob. 1.33PCh. 1 - Prob. 1.34PCh. 1 - Provide the following information about...Ch. 1 - Use the ball-and-stick model to answer each...Ch. 1 - Citric acid is responsible for the tartness of...Ch. 1 - Zingerone gives ginger its pungent taste. a.What...Ch. 1 - Assign formal charges to each carbon atom in the...Ch. 1 - Assign formal charges to each and atom in the...Ch. 1 - Prob. 1.41PCh. 1 - Prob. 1.42PCh. 1 - Prob. 1.43PCh. 1 - Draw all possible isomers for each molecular...Ch. 1 - 1.45 Draw Lewis structures for the nine isomers...Ch. 1 - Prob. 1.46PCh. 1 - Prob. 1.47PCh. 1 - Prob. 1.48PCh. 1 - Prob. 1.49PCh. 1 - Prob. 1.50PCh. 1 - Prob. 1.51PCh. 1 - Prob. 1.52PCh. 1 - Consider compounds A-D, which contain both a...Ch. 1 - Prob. 1.54PCh. 1 - Prob. 1.55PCh. 1 - 1.56 Consider the compounds and ions with curved...Ch. 1 - 1.57 Predict all bond angles in each...Ch. 1 - 1.58 Predict the geometry around each highlighted...Ch. 1 - Prob. 1.59PCh. 1 - Draw in all the carbon and hydrogen atoms in each...Ch. 1 - 1.61 Convert each molecule into a skeletal...Ch. 1 - Prob. 1.62PCh. 1 - Prob. 1.63PCh. 1 - Predict the hybridization and geometry around each...Ch. 1 - Prob. 1.65PCh. 1 - Ketene, , is an unusual organic molecule that has...Ch. 1 - Rank the following bonds in order of increasing...Ch. 1 - Prob. 1.68PCh. 1 - Two useful organic compounds that contain Cl atoms...Ch. 1 - Use the symbols + and to indicate the polarity of...Ch. 1 - Prob. 1.71PCh. 1 - Anacin is an over-the-counter pain reliever that...Ch. 1 - Answer the following questions about acetonitrile...Ch. 1 - Prob. 1.74PCh. 1 - 1.75 The principles of this chapter can be...Ch. 1 -
a. What is the hybridization of each N atom in...Ch. 1 - 1.77 Stalevo is the trade name for a medication...Ch. 1 - 1.78 and are two highly reactive carbon...Ch. 1 - 1.79 The N atom in (acetamide) is hybridized,...Ch. 1 - Prob. 1.80PCh. 1 - Prob. 1.81PCh. 1 - Prob. 1.82PCh. 1 - Prob. 1.83PCh. 1 - Prob. 1.84PCh. 1 - Prob. 1.85P
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- Two compounds have the molecular formula N3H3. One of the compounds, triazene, contains an NN bond; the other compound, triaziridene, does not. (a) Write the correct Lewis structures for each compound. (b) Approximate the bond angle between the three nitrogen atoms in each compound.arrow_forwardWhich of the following bonds is most polar: S¬Cl, S¬Br, Se¬Cl,or Se¬Br?arrow_forwardThe average bond energy (enthalpy) for a C=C double bond is 614 kJ/molkJ/mol and that of a C−C single bond is 348 kJ/molkJ/mol. If it takes 4.42×10−19 J/molecule to break the C=C double bond. What is the longest wavelength λ of light that will provide photons of sufficient energy to break the π bond and cause the isomerization? Express your answer numerically in nanometers.arrow_forward
- Carbon-carbon bonds form the “backbone” of nearly every organic and biological molecule. The average bond energy of the C¬C bond is 347 kJ/mol. Calculate the frequency and wavelength of the least energetic photon that can break an average C¬C bond. In what region of the electromagnetic spectrum is this radiation?arrow_forwardThe compound oxygen difluoride is quite reactive, giving oxygen and HF when treated with water: OF2(g) + H2O(g) → O2(g) + 2HF(g) ΔE°rxn = –318 kJ Using bond energies, calculate the bond dissociation energy of the O–F bond in OF2. Average Bond Energies (kJ/mol) Picture O–F bond dissociation energy = _____kJ/molarrow_forwardAnswer the questions in the table below about the shape of the trichlorostannanide How many electron groups are around the central tin atom? Note: one "electron group" means one lone pair, one single bond, one double bond, or one triple bond. What phrase best describes the arrangement of these electron groups around the central tin atom? (You may need to use the scrollbar to see all the choices.) 0 (choose one) X S SnC13) anion.arrow_forward
- There are two main types of covalent bond breakage. In ho-molytic breakage , each atom in the bond gets one of the shared electrons. In some cases, the electronega-tivity of adjacent atoms affects the bond energy. In heterolytic breakage, one atom gets both electrons and the other gets none;thus, a cation and an anion form. (a) Why is the C−C bond in H₃C−CF₃(423 kJ/mol) strongerthan that in H₃C−CH₃(376 kJ/mol)?(b) Use bond energy and any other data to calculate the heat ofreaction for the heterolytic cleavage of O₂.arrow_forward5. The reason there is danger in exposure to high-energy radiation (e.g., ultraviolet and X rays) is that the radiation can rupture chemical bonds. In some cases, cancer can be caused it. A carbon-carbon single bond has a bond energy of approximately 348 kJ per mole. What wavelength of light is required to provide sufficient energy to break the C-C bond? In which region of the electromagnetic spectrum is this wavelength located?arrow_forwardSodium fluoroacetate (NaO2C2H2F) is a common poison used in New Zealand to control invasive species, such as rats. It can be prepared by the substitution of a C-CI bond in sodium chloroacetate (NaO2C2H2CI) for a C-F bond. What is the approximate enthalpy change for this substitution reaction on a 5.000 mole sample, based on the following bond energies? C-CI = 339.0 kJ/mol C-F = 485.0 kJ/molarrow_forward
- Although carbon has four bonds in stable molecules, sometimes reactive carbon intermediates that contain carbon atoms without four bonds are formed for very short time periods. Examples of these unstable intermediates include the methyl carbocation (CH 3) + and the methyl carbanion (CH 3) −. Draw Lewis structures for both unstable ions and predict the shape around carbon.arrow_forwardDraw a Lewis structure for the ozone molecule, O3. (The order of atom attachment is O-O-O, and they do not form a ring.) Chemists use ozone to cleave carbon-carbon double bondsarrow_forwardDefine Compounds Containing C–Z σ Bonds ?arrow_forward
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