EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
9th Edition
ISBN: 9780136781776
Author: Wade
Publisher: PEARSON CO
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 8.14C, Problem 8.34P
Predict the major products of the following reactions, including stereochemistry.
- a. cyclohexene + KMnO4/H2O (cold, dilute)
- b. cyclohexene + peroxyacetic acid in water
- c. cis — pent — 2 — ene + OsO4/H2O2
- d. cis — pent — 2 — ene + peroxyacetic acid in water
- e. trans — pent — 2 ene + OsO4/H2O2
- f. trans — pent — 2 — ene + peroxyacetic acid in water
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Starting Materials
CH3B
CH3CH2BR
CH3CH2CH,Br
C6H5Br
Reagents
Mg, ether
1.
a.
2.
13CH2-13C-OH
b.
13CO2 then H3O*
3.
LIAIH4 then H3o*
PBr3
CO2 then H30*
C.
4.
d.
5.
C6HsCH2Br
е.
Select a starting material and a series of reagents necessary to synthesize this compound in as few steps as possible.
Enter your selection as a number for the starting material, followed by the letters of the reagents, in the order that you wish to use them, i.e. 3abcf.
B. Draw structures for the products formed in the following reactions. If more than one product is
possible, show all of them, and indicate the major product, if any.
HO
OH
1. KMnO4, NaOH
2. dil. H₂SO4, H₂O
Zn(Hg)
HCI
MnO₂
acetone
NCS
O
1. AICI3¹
2. Br₂, FeBr3
3. Zn(Hg), HCI
1. NBS
CI
2. KOtBu
The following synthetic route is used to prepare an intermediate in the total synthesis of
the anticholinergic drug benzilonium bromide.
Love
1. Br.
(A)
2. MeO Nat
(B)
3. H,O*
OMe
EINH,
OCH3
(C)
4. NaOH, H,O
6. NaBH,
(D)
ОН
5. Н,о+, heat
Et
(racemic)
Propose structural formulas for intermediates A, B, C, and D.
Chapter 8 Solutions
EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
Ch. 8.3A - Predict the major products of the following...Ch. 8.3A - a. When 1 mole of buta-1,3-diene reacts with 1...Ch. 8.3B - Predict the major products of the following...Ch. 8.3B - Show how you would accomplish the following...Ch. 8.4B - Propose a mechanism to show how...Ch. 8.4B - Predict the products of the following hydration...Ch. 8.6 - a. Propose a mochansm fortho following reaction....Ch. 8.6 - Prob. 8.8PCh. 8.6 - Prob. 8.9PCh. 8.7A - Prob. 8.10P
Ch. 8.7A - Prob. 8.11PCh. 8.7C - Prob. 8.12PCh. 8.7C - Prob. 8.13PCh. 8.7C - a. When (Z)-3-methylhex-3-ene undergoes...Ch. 8.7C - Prob. 8.15PCh. 8.7C - Prob. 8.16PCh. 8.8B - Prob. 8.17PCh. 8.8B - Prob. 8.18PCh. 8.9 - Prob. 8.19PCh. 8.9 - Prob. 8.20PCh. 8.9 - Prob. 8.21PCh. 8.9 - Prob. 8.22PCh. 8.10 - Prob. 8.23PCh. 8.10 - Prob. 8.24PCh. 8.10 - Prob. 8.25PCh. 8.11A - Prob. 8.26PCh. 8.11B - Prob. 8.27PCh. 8.11B - Prob. 8.28PCh. 8.12 - Prob. 8.29PCh. 8.13 - a. Propose a mechanism for the conversion of...Ch. 8.13 - Magnesium monoperoxyphthalate (MMPP) epoxidizes...Ch. 8.13 - Predict the major products of the following...Ch. 8.13 - When 1,2-epoxycyclohexane (cyclohexene oxide) is...Ch. 8.14C - Predict the major products of the following...Ch. 8.14C - Prob. 8.35PCh. 8.15B - Prob. 8.36PCh. 8.15C - Predict the major products of the following...Ch. 8.16A - Prob. 8.38PCh. 8.16A - Prob. 8.39PCh. 8.16B - Prob. 8.40PCh. 8.16B - Prob. 8.41PCh. 8.16C - Prob. 8.42PCh. 8.17B - Prob. 8.43PCh. 8.17B - Prob. 8.44PCh. 8.17B - Show how you would synthesize each compound,...Ch. 8 - Prob. 8.46SPCh. 8 - Prob. 8.47SPCh. 8 - Give the products expected when the following...Ch. 8 - Show how you would make the following compounds...Ch. 8 - Using 1,2-dimethylcyclohexene as your starting...Ch. 8 - Show how you would synthesize each compound using...Ch. 8 - Prob. 8.52SPCh. 8 - Show how you might use olefin metathesis to...Ch. 8 - Prob. 8.54SPCh. 8 - Prob. 8.55SPCh. 8 - Propose mechanisms consistent with the following...Ch. 8 - Prob. 8.57SPCh. 8 - Prob. 8.58SPCh. 8 - Draw a reaction-energy diagram for the propagation...Ch. 8 - Prob. 8.60SPCh. 8 - Prob. 8.61SPCh. 8 - Prob. 8.62SPCh. 8 - Prob. 8.63SPCh. 8 - Prob. 8.64SPCh. 8 - Prob. 8.65SPCh. 8 - Prob. 8.66SPCh. 8 - Prob. 8.67SPCh. 8 - Prob. 8.68SPCh. 8 - Prob. 8.69SPCh. 8 - Prob. 8.70SPCh. 8 - Prob. 8.71SPCh. 8 - Prob. 8.72SPCh. 8 - Prob. 8.73SPCh. 8 - Prob. 8.74SPCh. 8 - Prob. 8.75SPCh. 8 - Prob. 8.76SPCh. 8 - Prob. 8.77SPCh. 8 - Prob. 8.78SPCh. 8 - Prob. 8.79SP
Additional Science Textbook Solutions
Find more solutions based on key concepts
During the early part of the 20th century, sulfanilamide (an antibacterial drug) was only administered by injec...
Elementary Principles of Chemical Processes, Binder Ready Version
Calculate the lattice energy of CaCl2 using a Born-Haber cycle and data from Appendices F and L and Table 7.5. ...
Chemistry & Chemical Reactivity
Fully developed conditions are known to exist for water flowing through a 25-nim-diameer tube at 0.01 kg/s and ...
Fundamentals of Heat and Mass Transfer
45. Calculate the mass of nitrogen dissolved at room temperature in an 80.0-L home aquarium. Assume a total pre...
Chemistry: Structure and Properties
Consider a sample of ideal gas initially in a volume V at temperature T and pressure P. Does the entropy of thi...
General Chemistry: Principles and Modern Applications (11th Edition)
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- 21. Provide the structures of the organic products in the following reactions: Br HO (Z)-vinyl halide 2013 Pearson Education, Inc. p-iodophenol ©2013 Pearson Education Inc Br + + B OR OR (E)-alkenylboronate ester B OH OH phenylboronic acid Pd(PPH3)4 NaOH 10% Pd/C K₂CO3, H₂O Carrow_forwardDraw the organic products formed when allylic alcohol A is treated with each reagent.a.H2 + Pd-C b.mCPBA c. PCC d.CrO3, H2SO4, H2O e.(CH3)3COOH, Ti[OCH(CH3)2]4, (+)-DET f. (CH3)3COOH, Ti[OCH(CH3)2]4, (−)-DET g. [1] PBr3; [2] LiAlH4; [3] H2O h.HCrO4−–Amberlyst A-26 resinarrow_forwardto 1. conc. HBr H20 Br OH O Na 2. Na NH2 NH3 d = El Elimination f = SN1 Nucleophilic substitution a = Proton transfer b = Lewis acid/base e = E2 Elimination g = SN2 Nucleophilic substitution c = Electrophilic addition The rections above involve synthesis or reactions of alcohols and ethers. Identify the mechanism by which they proceed from among the mechanisms listed. Use the letters a - g for your answers. 1. 2. Submit Answer Retry Entire Group 8 more group attempts remainingarrow_forward
- [Review Topics] [References] HO pyridine 1. SOCIl, + sO2 + H. Aqueous acetone H3C H20 H3C HBr 2. Br H OH optically active racemic f = SN1 Nucleophilic substitution g = SN2 Nucleophilic substitution a = Proton transfer d = E1 Elimination b = Lewis acid/base e = E2 Elimination c = Electrophilic addition The rections above involve synthesis or reactions of alcohols and ethers. Identify the mechanism by which they proceed from among the mechanisms listed. Use the letters a - g for your answers. 1. 2.arrow_forwardHw.33.arrow_forwardNH₂ NHỊCH, tipy (a) acrylamide Diamines are used as the building blocks for the synthesis of pharmaceuticals and agrochemicals. In the above synthesis, draw the structure of the product (b). ChemDoodle 1. LIAIH 2. H₂O • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Include cationic counter-ions, e.g., Na* in your answer, but draw them in their own sketcher. OF (b) 6arrow_forward
- 6. Given the reactions below, provide the missing products and explain the differences among the hydride reactions. Where is stereochemistry is present, does it change or stay the same? 1. LİAIH4, THF 1. NaBH4, EtOH 2. H;O* 2. H3O* + NH 1. LİAIH4, THF 1. NABH4, EtOH 2. H3O* 2. H;O* ОН 1. LİAIH4, THF 1. NaBH4, ETOH 2. H3O* 2. H3O*arrow_forwardAlcohols are important for organic synthesis, especially in situations involving alkenes. The alcohol might be the desired product, or the OH group might be transformed into another functional group via halogenation, oxidation, or perhaps conversion to a sulfonic ester derivative. Formation of an alcohol from an alkene is particularly powerful because conditions can be chosen to produce either the Markovnikov or non-Markovnikov product from an unsymmetrical alkene. Using your reaction roadmap as a guide, show how to convert 4-methyl-1-pentene into 5-methylhexanenitrile. You must use 4-methyl-1-pentene and sodium cyanide as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.arrow_forward3. cyclohexanone to cyclohexane. A second year chemistry student is assigned a task to prepare compound 2 from compound 1 using lithium aluminium hydride as a reducing agent. However, from the reaction mixture, no traces of product 2 were detected. Explain this observation in detail and suggest an alternative route that will lead to product 2. H 1 CH3 LiAllH4 H O: 2 CH3 quearrow_forward
- Please complete boxed reactions. Thanks. P.s. this is not graded work but a study guide.arrow_forwardChemistry Part 5 out of 6 Choose the most appropriate reagent(s) for the conversion of 1-phenylethyl bromide to methyl 1-phenylethyl sulfide. A H₂S C CH₂SH NBS, ROOR CCI4 heat E CH₂SO₂H Br BSg, NaOH reagent(s) DNaSCH3, DMF SCH3arrow_forwardDd.40.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Coenzymes and cofactors; Author: CH15 SWAYAM Prabha IIT Madras;https://www.youtube.com/watch?v=bubY2Nm7hVM;License: Standard YouTube License, CC-BY
Aromaticity and Huckel's Rule; Author: Professor Dave Explains;https://www.youtube.com/watch?v=7-BguH4_WBQ;License: Standard Youtube License