Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 1.15, Problem 44P
a. What is the hybridization of each of the carbon atoms in the following compound?
b. What is the hybridization of each of the C, N. and O atoms in the following compounds:
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Draw the stepwise mechanism for the reactions
Part I.
a)
Draw reaction mechanism for the transformations of benzophenone to benzopinacol to benzopinaco lone
b) Pinacol (2,3-dimethyl, 1-3-butanediol) on treatment w/ acid gives a mixture of pina colone
(3,3-dimethyl-2-butanone) and 2, 3-dimethyl - 1,3-butadiene. Give reasonable mechanism
the formation of
the products
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3. The explosive decomposition of 2 mole of TNT (2,4,6-trinitrotoluene) is shown below:
Assume the C(s) is soot-basically atomic carbon (although it isn't actually atomic carbon in real life).
2
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NO2
NO2
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a. Use bond dissociation energies to calculate how much AU is for this reaction in kJ/mol.
Chapter 1 Solutions
Organic Chemistry (8th Edition)
Ch. 1.1 - Oxygen has three isotopes, 16O, 17O, and 18O. The...Ch. 1.1 - a. How many protons do the following species...Ch. 1.1 - Chlorine has two isotopes, 35Cl and 37Cl; 75.77%...Ch. 1.2 - Prob. 4PCh. 1.2 - a. Write the ground-state electronic configuration...Ch. 1.2 - Look at the relative positions of each pair of...Ch. 1.3 - a. Find potassium (K) in the periodic table and...Ch. 1.3 - Which bond is more polar? a. b. c. d.Ch. 1.3 - Which of the following has a. the most polar bond?...Ch. 1.3 - Use the symbols + and to show the direction of...
Ch. 1.3 - Explain why HCL has a smaller dipole moment than...Ch. 1.3 - After examining the potential maps for LiH, HF,...Ch. 1.4 - An atom with a formal charge does not necessarily...Ch. 1.4 - Prob. 16PCh. 1.4 - a. Draw two Lewis structure for C2H6O. b. Draw...Ch. 1.4 - Draw the lone-pair electrons that are not shown in...Ch. 1.4 - Prob. 20PCh. 1.4 - Which of the atoms in the molecular models in...Ch. 1.4 - Prob. 22PCh. 1.4 - Prob. 23PCh. 1.5 - Draw the following orbitals: a. 3s orbital b. 4s...Ch. 1.6 - Prob. 25PCh. 1.6 - Indicate the kind of molecular orbital (, , , or )...Ch. 1.7 - What orbitals are used to form the 10 sigma bonds...Ch. 1.7 - Explain why a bond formed by overlap of s orbital...Ch. 1.9 - Put n number in each of the blanks: a. __ s...Ch. 1.9 - For each of the given species: a. Draw its Lewis...Ch. 1.11 - Predict the approximate bond angles in a. the...Ch. 1.11 - According to the potential map for the ammonium...Ch. 1.12 - Prob. 35PCh. 1.13 - a. What are the relative lengths and strengths of...Ch. 1.13 - Prob. 38PCh. 1.14 - Describe the orbitals used in bonding and the bond...Ch. 1.15 - Which of the bond in a carbon-oxygen double bond...Ch. 1.15 - Would you expect a CC bond formed by sp2sp2...Ch. 1.15 - Caffeine is a natural insecticide found in the...Ch. 1.15 - a. What is the hybridization of each of the carbon...Ch. 1.15 - Predict the approximate bond angles for a. the CNC...Ch. 1.16 - What of the following molecules would you expect...Ch. 1.16 - Account for the difference in the shape and color...Ch. 1.16 - If the dipole moment of CH3F is 1.847 D and the...Ch. 1 - Draw a Lewis structure for each of the following:...Ch. 1 - Prob. 50PCh. 1 - What is the hybridization of all the atoms (other...Ch. 1 - Draw the condensed structure of a compound that...Ch. 1 - Predict the approximate bond angles: a. the CNH...Ch. 1 - Prob. 54PCh. 1 - Draw a Lewis structure for each of the following:...Ch. 1 - What is the hybridization of each of the carbon...Ch. 1 - Rank the bonds from most polar. a. CO, CF, CN b....Ch. 1 - Draw a Lewis structure for each of the following:...Ch. 1 - Prob. 59PCh. 1 - What is the hybridization of the indicated atom in...Ch. 1 - Predict the approximate bond angles for the...Ch. 1 - Prob. 62PCh. 1 - Draw the missing lone-pair electrons and assigns...Ch. 1 - a. Which of the indicated bonds in each molecule...Ch. 1 - For each of the following molecules, indicate the...Ch. 1 - Draw a Lewis structure for each of the following:...Ch. 1 - Prob. 67PCh. 1 - Rank the following compounds from highest dipole...Ch. 1 - In which orbitals are the lone pairs in nicotine?Ch. 1 - Prob. 70PCh. 1 - Prob. 71PCh. 1 - a. Which of the species have bond angles of 109.5?...Ch. 1 - Prob. 73PCh. 1 - Which compound has a larger dipole moment: CH3Cl...Ch. 1 - Prob. 75PCh. 1 - Explain why CH3Cl has a greater dipole moment than...Ch. 1 - a. Draw a Lewis structure for each of the...Ch. 1 - There are three isomers with molecular formula...
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- Part I. Draw reaction mechanism for the transformations of benzophenone to benzopinacol to benzopinaco lone and answer the ff: Pinacol (2,3-dimethyl, 1-3-butanediol) on treatment w/ acid gives a mixture of pina colone and (3,3-dimethyl-2-butanone) 2,3-dimethyl-1,3-butadiene. Give reasonable mechanism the formation of the products Forarrow_forwardShow the mechanism for these reactionsarrow_forwardDraw the stepwise mechanismarrow_forward
- Draw a structural formula of the principal product formed when benzonitrile is treated with each reagent. (a) H₂O (one equivalent), H₂SO₄, heat (b) H₂O (excess), H₂SO₄, heat (c) NaOH, H₂O, heat (d) LiAlH4, then H₂Oarrow_forwardDraw the stepwise mechanism for the reactionsarrow_forwardDraw stepwise mechanismarrow_forward
- Part I. Draw reaction mechanism for the transformations of benzophenone to benzopinacol to benzopinaco lone and answer the ff: a) Give the major reason for the exposure of benzophenone al isopropyl alcohol (w/acid) to direct sunlight of pina colone Mechanism For b) Pinacol (2,3-dimethy 1, 1-3-butanediol) on treatment w/ acid gives a mixture (3,3-dimethyl-2-butanone) and 2, 3-dimethyl-1,3-butadiene. Give reasonable the formation of the productsarrow_forwardwhat are the Iupac names for each structurearrow_forwardWhat are the IUPAC Names of all the compounds in the picture?arrow_forward
- 1) a) Give the dominant Intermolecular Force (IMF) in a sample of each of the following compounds. Please show your work. (8) SF2, CH,OH, C₂H₂ b) Based on your answers given above, list the compounds in order of their Boiling Point from low to high. (8)arrow_forward19.78 Write the products of the following sequences of reactions. Refer to your reaction road- maps to see how the combined reactions allow you to "navigate" between the different functional groups. Note that you will need your old Chapters 6-11 and Chapters 15-18 roadmaps along with your new Chapter 19 roadmap for these. (a) 1. BHS 2. H₂O₂ 3. H₂CrO4 4. SOCI₂ (b) 1. Cl₂/hv 2. KOLBU 3. H₂O, catalytic H₂SO4 4. H₂CrO4 Reaction Roadmap An alkene 5. EtOH 6.0.5 Equiv. NaOEt/EtOH 7. Mild H₂O An alkane 1.0 2. (CH3)₂S 3. H₂CrO (d) (c) 4. Excess EtOH, catalytic H₂SO OH 4. Mild H₂O* 5.0.5 Equiv. NaOEt/EtOH An alkene 6. Mild H₂O* A carboxylic acid 7. Mild H₂O* 1. SOC₁₂ 2. EtOH 3.0.5 Equiv. NaOEt/E:OH 5.1.0 Equiv. NaOEt 6. NH₂ (e) 1. 0.5 Equiv. NaOEt/EtOH 2. Mild H₂O* Br (f) i H An aldehyde 1. Catalytic NaOE/EtOH 2. H₂O*, heat 3. (CH,CH₂)₂Culi 4. Mild H₂O* 5.1.0 Equiv. LDA Br An ester 4. NaOH, H₂O 5. Mild H₂O* 6. Heat 7. MgBr 8. Mild H₂O* 7. Mild H₂O+arrow_forwardLi+ is a hard acid. With this in mind, which if the following compounds should be most soluble in water? Group of answer choices LiBr LiI LiF LiClarrow_forward
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