Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 1, Problem 1.75P
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
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 - Draw Lewis structures for each molecular formula....Ch. 1 - Prob. 1.9PCh. 1 - Prob. 1.10P
Ch. 1 - Prob. 1.11PCh. 1 - Prob. 1.12PCh. 1 - Draw a second resonance structure for each...Ch. 1 - Prob. 1.14PCh. 1 - Draw a second resonance structure for nitrous...Ch. 1 - Prob. 1.16PCh. 1 - Prob. 1.17PCh. 1 - Prob. 1.18PCh. 1 - Prob. 1.19PCh. 1 - Prob. 1.20PCh. 1 - Simplify each condensed structure by using...Ch. 1 - Prob. 1.22PCh. 1 - Prob. 1.23PCh. 1 - Convert each skeletal structure to a complete...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 - Classify each bond in the following molecules as ...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 - Two radioactive isotopes of iodine used for the...Ch. 1 - Prob. 1.40PCh. 1 - Assign formal charges to each carbon atom in the...Ch. 1 - Assign formal charges to each N and O atom in the...Ch. 1 - Draw one valid Lewis structure for each compound....Ch. 1 - Prob. 1.44PCh. 1 - Prob. 1.45PCh. 1 - Prob. 1.46PCh. 1 - Draw all possible isomers for each molecular...Ch. 1 - 1.45 Draw Lewis structures for the nine isomers...Ch. 1 - Prob. 1.49PCh. 1 - Prob. 1.50PCh. 1 - Prob. 1.51PCh. 1 - Prob. 1.52PCh. 1 - Prob. 1.53PCh. 1 - Prob. 1.54PCh. 1 - Draw all reasonable resonance structures for each...Ch. 1 - Prob. 1.56PCh. 1 - Rank the resonance structures in each group in...Ch. 1 - 1.56 Consider the compounds and ions with curved...Ch. 1 - 1.57 Predict all bond angles in each...Ch. 1 - Predict the geometry around each indicated atom....Ch. 1 - Prob. 1.61PCh. 1 - Prob. 1.62PCh. 1 - Draw in all the carbon and hydrogen atoms in each...Ch. 1 - Prob. 1.64PCh. 1 - Prob. 1.65PCh. 1 - Prob. 1.66PCh. 1 - Prob. 1.67PCh. 1 - Each of the following condensed or skeletal...Ch. 1 - Prob. 1.69PCh. 1 - Prob. 1.70PCh. 1 - Prob. 1.71PCh. 1 - Prob. 1.72PCh. 1 - Prob. 1.73PCh. 1 - Prob. 1.74PCh. 1 - Two useful organic compounds that contain Cl atoms...Ch. 1 - Use the symbols + and to indicate the polarity of...Ch. 1 - Label the polar bonds in each molecule. Indicate...Ch. 1 - Answer the following questions about acetonitrile...Ch. 1 - Prob. 1.79PCh. 1 - The principles of this chapter can be applied to...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. 1.85PCh. 1 - Prob. 1.86PCh. 1 - Prob. 1.87PCh. 1 - Prob. 1.88PCh. 1 - Prob. 1.89PCh. 1 - Prob. 1.90P
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- Which of the following bonds is most polar: S¬Cl, S¬Br, Se¬Cl,or Se¬Br?arrow_forwardA 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_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
- 5. 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_forwardDefine Compounds Containing C–Z σ Bonds ?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_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_forward
- Bond 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_forwardThe hyponitrite ion, ONNO, exists in solid compounds as the trans isomer. Using valence bond theory, explain why cistrans isomers might be expected for this ion. Draw structural formulas of the cistrans isomers.arrow_forwardBorax has the molecular formula Na2B4O5(OH)4. The structure of the anion in this compound is shown below. What is the electron pair geometry and molecular geometry surrounding each of the boron atoms in this anion? What hybridization can be assigned to each of the boron atoms? What is the formal charge of each boron atom?arrow_forward
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