Organic Chemistry - With Access (Custom)
9th Edition
ISBN: 9781337031745
Author: McMurry
Publisher: Cengage
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Chapter 4.SE, Problem 61AP
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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 4 Solutions
Organic Chemistry - With Access (Custom)
Ch. 4.1 - Give IUPAC names for the following cycloalkanes:Ch. 4.1 - Draw structures corresponding to the following...Ch. 4.1 - Name the following cycloalkane:Ch. 4.2 - Prob. 4PCh. 4.2 - Draw the structures of the following molecules:...Ch. 4.2 - Prostaglandin F2α, a hormone that causes uterine...Ch. 4.2 - Name the following substances, including the cis-...Ch. 4.3 - Each H↔H eclipsing interaction in ethane costs...Ch. 4.3 - cis-1, 2-Dimethylcyclopropane has more strain than...Ch. 4.4 - Prob. 10P
Ch. 4.4 - Two conformations of cis-l, 3-dimethylcyclobutane...Ch. 4.6 - Draw two different chair conformations of...Ch. 4.6 - Draw two differant chair conformations of trans-1,...Ch. 4.6 - Prob. 14PCh. 4.7 - What is the energy difference between the axial...Ch. 4.7 - Prob. 16PCh. 4.7 - Look at Figure 4-12 on page 105, and estimate the...Ch. 4.8 - Draw the more stable chair conformation of the...Ch. 4.8 - Identify each substituent in the following...Ch. 4.9 - Which isomer is more stable, cis-decalin or...Ch. 4.9 - Look at the following structure of the female...Ch. 4.SE - Prob. 22VCCh. 4.SE - Name the following compound, identify each...Ch. 4.SE - A trisubstituted cyclohexane with three...Ch. 4.SE - The following cyclohexane derivative has three...Ch. 4.SE - Prob. 26VCCh. 4.SE - Draw the five cycloalkanes with the formula C5H10.Ch. 4.SE - Draw two constitutional isomers of cis-1,...Ch. 4.SE - Prob. 29APCh. 4.SE - Tell whether the following pairs of compounds are...Ch. 4.SE - Prob. 31APCh. 4.SE - Prob. 32APCh. 4.SE - Draw 1, 3, 5-trimethylcyclohexane using a hexagon...Ch. 4.SE - Hydrocortisone, a naturally occurring hormone...Ch. 4.SE - A 1, 2-cis disubstituted cyclohexane, such as...Ch. 4.SE - A 1, 2-trans disubstituted cyclohexane must have...Ch. 4.SE - Prob. 37APCh. 4.SE - Which is more stable, a 1, 4-trans disubstituted...Ch. 4.SE - cis-1, 2-Dimethylcyclobutane is less stable than...Ch. 4.SE - From the data in Figure 4-12 and Table 4-1,...Ch. 4.SE - Prob. 41APCh. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Galactose, a sugar related to glucose, contains a...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - The diaxial conformation of cis-1,...Ch. 4.SE - Approximately how much steric strain does the...Ch. 4.SE - In light of your answer to Problem 4-43, draw the...Ch. 4.SE - Prob. 50APCh. 4.SE - Prob. 51APCh. 4.SE - Using molecular models as well as structural...Ch. 4.SE - trans-Decalin is more stable than its cis isomer,...Ch. 4.SE - As mentioned in Problem 3-53, the statin drugs,...Ch. 4.SE - myo-Inositol, one of the isomers of...Ch. 4.SE - How many cis–trans stereoisomers of myo-inositol...Ch. 4.SE - The German chemist J. Bredt proposed in 1935 that...Ch. 4.SE - Tell whether each of the following substituents on...Ch. 4.SE - Prob. 59APCh. 4.SE - Prob. 60APCh. 4.SE - Ketones react with alcohols to yield products...Ch. 4.SE - Alcohols undergo an oxidation reaction to yield...
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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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Chapter 4 Alkanes and Cycloalkanes Lesson 2; Author: Linda Hanson;https://www.youtube.com/watch?v=AL_CM_Btef4;License: Standard YouTube License, CC-BY
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