Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 1, Problem 72P
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?
The 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.
Chapter 1 Solutions
Organic Chemistry (6th Edition)
Ch. 1.1 - While the most common isotope of nitrogen has a...Ch. 1.2 - Label each bond in the following compounds as...Ch. 1.3 - Draw a valid Lewis structure for each species. a....Ch. 1.3 - Prob. 9PCh. 1.4 - Draw Lewis structures for each molecular formula....Ch. 1.6 - Classify each pair of compounds as isomers or...Ch. 1.6 - Prob. 12PCh. 1.6 - Prob. 13PCh. 1.6 - Prob. 14PCh. 1.6 - Prob. 16P
Ch. 1.6 - Prob. 17PCh. 1.7 - Prob. 18PCh. 1.7 - Prob. 19PCh. 1.7 - Using the principles of VSEPR theory, you can...Ch. 1.8 - Convert each condensed formula to a Lewis...Ch. 1.8 - Prob. 22PCh. 1.8 - Prob. 23PCh. 1.8 - Convert each skeletal structure to a complete...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 and atom in the...Ch. 1 - Prob. 44PCh. 1 - Prob. 46PCh. 1 - Draw all possible isomers for each molecular...Ch. 1 - 1.45 Draw Lewis structures for the nine isomers...Ch. 1 - Prob. 52PCh. 1 - Prob. 53PCh. 1 - Prob. 54PCh. 1 - Consider compounds A-D, which contain both a...Ch. 1 - Draw in all the carbon and hydrogen atoms in each...Ch. 1 - 1.61 Convert each molecule into a skeletal...Ch. 1 - Prob. 65PCh. 1 - Predict the hybridization and geometry around each...Ch. 1 - Prob. 68PCh. 1 - Ketene, , is an unusual organic molecule that has...Ch. 1 - Rank the following bonds in order of increasing...Ch. 1 - Two useful organic compounds that contain Cl atoms...Ch. 1 - Use the symbols + and to indicate the polarity of...Ch. 1 - Prob. 74PCh. 1 - Anacin is an over-the-counter pain reliever that...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. 83PCh. 1 - Prob. 84PCh. 1 - Prob. 85PCh. 1 - Prob. 86PCh. 1 - Prob. 87PCh. 1 - Prob. 88P
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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_forwardThere 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_forward
- 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.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_forwardWhich bond is most likely to be the location of a chemical reaction: C=N, C¬C, or C¬H?arrow_forward
- Draw 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_forwardFormic acid (HCOOH; structural formula shown below) is secreted by certain species of ants when they bite. Rank the relative strengths of (a) the C-O and C=O bonds and (b) the H¬C and H¬O bonds. Explain these rankings.arrow_forwardDefine Compounds Containing C–Z σ Bonds ?arrow_forward
- Complete the following resonance structures for POCl3. a. Would you predict the same molecular structure from each resonance structure? b. What is the hybridization of P in each structure? c. What orbitals can the P atom use to form the bond in structure B? d. Which resonance structure would be favored on the basis of formal charges?arrow_forwardIn addition to CO, CO2, and C3O2, there is another molecular oxide of carbon, pentacarbon dioxide, C5O2, a yellow solid. (a) What is the approximate C-to-C-to-O bond angle in pentacarbon dioxide? (b) What is the approximate C-to-C-to-C bond angle in this compound?arrow_forwardBond Enthalpy When atoms of the hypothetical element X are placed together, they rapidly undergo reaction to form the X2 molecule: X(g)+X(g)X2(g) a Would you predict that this reaction is exothermic or endothermic? Explain. b Is the bond enthalpy of X2 a positive or a negative quantity? Why? c Suppose H for the reaction is 500 kJ/mol. Estimate the bond enthalpy of the X2 molecule. d Another hypothetical molecular compound, Y2(g), has a bond enthalpy of 750 kJ/mol, and the molecular compound XY(g) has a bond enthalpy of 1500 kJ/mol. Using bond enthalpy information, calculate H for the following reaction. X2(g)+Y2(g)2XY(g) e Given the following information, as well as the information previously presented, predict whether or not the hypothetical ionic compound AX is likely to form. In this compound, A forms the A+ cation, and X forms the X anion. Be sure to justify your answer. Reaction: A(g)+12X2(g)AX(s)The first ionization energy of A(g) is 400 kJ/mol. The electron affinity of X(g) is 525 kJ/mol. The lattice energy of AX(s) is 100 kJ/mol. f If you predicted that no ionic compound would form from the reaction in Part e, what minimum amount of AX(s) lattice energy might lead to compound formation?arrow_forward
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