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Organic Chemistry: A Guided Inquiry

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter14: Elimination

Section: Chapter Questions

Problem 36CTQ

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Question

17. What can you say about the reaction below?
1. OsO4
2. NaHSO3
?
A. This reaction will generate cyclohexanol
B. This experiment will generate cis-1,2-cyclohexanediol
C. This reaction will generate a mixture of R,R-1,2-cyclohexanediol and the S,S-enantiomer
D. This experiment will generate trans-1,3-cyclohexanediol
E. This reaction will follow Markovnikov's rule

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The reaction below involves 2-chloropentane reacting with water. The product of this reaction is 2-pentanol. What would be the stereochemical result of the product? CH3 OH c CH;CH2CH3 H20 H. a. 100% R b. 100% S O C. ~50% R, ~50% S
Which is the main product when 2-methylbuta-1,3-diene reacts with one equivalent of HBr at room temperature for a prolonged time ? O a. Br O b. Br С. Br O d. Br
Draw the products of the following reactions. If the products can exist as stereoisomers show what stereoisomers are formed. a. cis-2-pentene + Br2/CH2Cl2 b. trans-2-pentene + Br2/CH2Cl2 c. 1- butene + HCl d. methylcyclohexene + HBr e. trans-3-hexene + Br2/CH2Cl2 f. cis-3-hexene + Br2/CH2Cl2 g. 3,3-dimethyl-1-pentene + HBr h. cis-2-butene + HBr i. (Z)-2,3-dichloro-2-butene + H2, Pd/C j. (E)-2,3-dichloro-2-butene + H2, Pd/C k. (Z)-3,4-dimethyl-3-hexene + H2, Pd/C l. (E)-3,4-dimethyl-3-hexene + H2, Pd/C
10. Write out the mechanism (intermediate/transition state) for this reaction. Indicate stereochemistry in product. H₂C Br H KOH S2
2. Consijder the reactiojn scheme below a. Draw the major product of this reaction. Show clearly (using wedge-and-dash lines) all stereoisomers formed under these reaction conditions. 1. BH3:THF 2. H2O2, NaOH b. What is the stereochemical relationship between the different stereoisomer products you drew in part 2a.?
What is the major product of the shown reaction ? 1.) BD3 2.) D2Ó2 H H D D CEC-H D D A D D D D Deuterium (chemical symbol - D) is a heavy isotope of hydrogen. C O1.A O 2. C 3. this reaction won't proceed as shown O5. B
27. Which is the expected product for the reaction of propyne with excess HBr?. A. 1-bromopropane B. 2-bromopane C. 2,2-dibromopropane D. 1,1-dibromopropane 28. The following compounds undergo electrophilic aromatic substitution EXCEPT I. A. I and II B. III and IV C. II and III D. III II. III. IV.
a. What is the major monobromination product of the following reaction? Disregard stereoisomers. b. What is the anticipated percent yield of the major product (as a percentage of all the monobrominated products)?
8. Circle the reactions that are synthetically useful (i.e.give only one major product). ~ Br₂, hv Cl₂, hv A NBS, hv NBS, hv
6. Circle the product of the following reaction. 1. C=C-H 2. H2O НО Н H H3C . I H3C OH Н || Н сан Н Н.с о IV H Н
Which one shows aromacity? OA. Cycloheptatrienyl anion. B. Cyclopentadienyl anion OC Cyclopentadienyl cation D. Cyclopentadienyl free radical
10. Draw the most stable resonance form for the intermediate in the following electrophilic substitution reaction.

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