ORGANIC CHEMISTRY
6th Edition
ISBN: 9781266633973
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 18.9, Problem 17P
Draw the products (including stereoisomers) formed when benzaldehyde
a.
b. 
c. 
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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
For
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
CH3
H
NO2
NO2
3N2 (g)+7CO (g) + 5H₂O (g) + 7C (s)
H
a. Use bond dissociation energies to calculate how much AU is for this reaction in kJ/mol.
Chapter 18 Solutions
ORGANIC CHEMISTRY
Ch. 18.1 - Rank the following compounds in order of...Ch. 18.1 - Prob. 2PCh. 18.2 - Give the IUPAC name for each aldehyde.Ch. 18.2 - Prob. 4PCh. 18.2 - Give the IUPAC name for each ketone.Ch. 18.5 - Prob. 11PCh. 18.9 - Problem 21.17 Draw the products of the following...Ch. 18.9 - Problem 21.18 Outline a synthesis of each Wittig...Ch. 18.9 - Problem 21.19 Draw the products (including...Ch. 18.9 - Problem 21.20 What starting materials are needed...
Ch. 18.9 - Prob. 19PCh. 18.10 - Problem 21.22 The product formed when reacts with...Ch. 18.10 - Prob. 21PCh. 18.11 - Prob. 22PCh. 18.11 - Prob. 23PCh. 18.11 - Prob. 24PCh. 18.12 - Prob. 25PCh. 18.12 - Problem 21.28 Draw a stepwise mechanism for the...Ch. 18.13 - Problem 21.29 Draw the products of each...Ch. 18 - Problem 21.40 (a) Give the IUPAC name for A and B....Ch. 18 - 21.41 Rank the following compounds in order of...Ch. 18 - Prob. 39PCh. 18 - 21.43 Give the IUPAC name for each compound.
a....Ch. 18 - 21.44 Give the structure corresponding to each...Ch. 18 - Prob. 42PCh. 18 - 21.46 Draw the products of each reaction.
a. e....Ch. 18 - Prob. 44PCh. 18 - 21.48 Draw all stereoisomers formed in each...Ch. 18 - Prob. 54PCh. 18 - Prob. 55PCh. 18 - Prob. 56PCh. 18 - Devise a synthesis of each alkene using a Wittig...Ch. 18 - Prob. 60PCh. 18 - Prob. 62PCh. 18 - Prob. 63PCh. 18 - 21.64 Draw a stepwise mechanism for the following...Ch. 18 - 21.65 Draw a stepwise mechanism f or the following...Ch. 18 - Prob. 67PCh. 18 - 21.67 Draw a stepwise mechanism for each...Ch. 18 - Prob. 69PCh. 18 - Prob. 70P
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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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