Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 9, Problem 23P
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[5] Write the structure of the product of the reaction of (S)-3-bromo-3-methylhexane
with ethanol (CH,CH,OH).
a) When (Z)-3-methylhex-3-ene undergoes hydroboration–oxidation, two isomeric products are formed. Give their structures, and label each asymmetric carbon atom as (R) or (S). What is the relationship between these isomers?
The heat of hydrogenation of cis-2,2,5,5-tetramethyl-3-hexene is -154 kJ (-36.7 kcal)/ mol, while that of the trans isomer is only -113 kJ (-26.9 kcal)/mol.
Q.) If a catalyst could be found that allowed equilibration of the cis and trans isomers at room temperature (such catalysts do exist), what would be the ratio of trans to cis isomers?
Chapter 9 Solutions
Organic Chemistry - Standalone book
Ch. 9.1 - Prob. 1PCh. 9.2 - Prob. 2PCh. 9.4 - How do bond distances and bond strengths change...Ch. 9.5 - Complete each of the following equations to show...Ch. 9.6 - Prob. 5PCh. 9.6 - Which of the alkynes of molecular formula C5H8 can...Ch. 9.7 - Give the structures of three isomeric dibromides...Ch. 9.7 - Prob. 8PCh. 9.9 - Write a series of equations showing how you could...Ch. 9.9 - Write a series of equations showing how to prepare...
Ch. 9.10 - Prob. 11PCh. 9.11 - Give the structure of the enol formed by hydration...Ch. 9.11 - Prob. 13PCh. 9.13 - Prob. 14PCh. 9.14 - Prob. 15PCh. 9 - Provide the IUPAC name for each of the following...Ch. 9 - Prob. 17PCh. 9 - All compounds in Problem 9.17 are isomers except...Ch. 9 - Prob. 19PCh. 9 - Write structural formulas for all the alkynes of...Ch. 9 - Prob. 21PCh. 9 - Prob. 22PCh. 9 - The alkane formed by hydrogenation of...Ch. 9 - Write the structure of the major organic product...Ch. 9 - Write the structure of the major organic product...Ch. 9 - When 2-heptyne was treated with aqueous sulfuric...Ch. 9 - Prob. 27PCh. 9 - Prob. 28PCh. 9 - Prob. 29PCh. 9 - Show by writing appropriate chemical equations how...Ch. 9 - Show by writing appropriate chemical equations how...Ch. 9 - Diphenylacetylene can be synthesized by the double...Ch. 9 - (Z)-9-tricosene [ (Z)-CH3(CH2)7CH=CH(CH2)12CH3 ]...Ch. 9 - Prob. 34PCh. 9 - Prob. 35PCh. 9 - Prob. 36PCh. 9 - Alkynes undergo hydroboration to give...Ch. 9 - Prob. 38DSPCh. 9 - Prob. 39DSPCh. 9 - Prob. 40DSPCh. 9 - Prob. 41DSPCh. 9 - Thinking Mechanistically About Alkynes The...
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- Given that five isomeric compounds (A, B, C, D, E) with the molecular formula C5H10O were subjected to chemical tests after undergoing Clemmensen reduction compounds A,B, and C all yielded n-pentane, the results of these tests are provided in the table below. Can you draw the structures of compounds A to E based on the outcomes of the chemical tests?arrow_forwardButadiene sulfone decomposes to 1,3-butadiene on heating. What would be the product of the following reaction of butadiene sulfone and 2-cyclohexenone with heat?arrow_forwardWhen bromine is added to two beakers, one containing phenyl isopropyl ether and the other containing cyclohexene, the bromine color in both beakers disappears. What observation could you make while performing this test that would allow you to distinguish the alkene from the aryl ether?arrow_forward
- Acrolein and 1,3-cyclohexadiene react in a one-step concerted manner to yield a single product. Give the structure of the product. What kind of reaction is this an example of? In terms of this reaction, how would you classify acrolein? How would you classify 1,3-cyclohexadiene? Hint: acrolein is not a systematic name so you may need to look up its structure if you are not already familiar with it.arrow_forward(1) Name the major product of the reaction between (S)-2-bromohexane and KCH3COO. Be specific with the configuration. (2) Name the alcohol that will produce the most stable intermediate and the dehydration product 2-methyl-1,3-pentadiene. (3) Give the name of the product between benzyl alcohol and pyridinium chlorochromate.arrow_forwarda) What products would you expect from the elimination reaction of 3-Bromo-2- methylpentane? Show the reaction by writing the condensed structural formula of the reactants and products. Identify the major and minor products. b) What alkyl halide might the 3,6-Dimethyl-1- heptene have been made from?arrow_forward
- Compounds X and Y both have the formula C7H₁4. Both X and Y react with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2-methylhexane. The heat of hydrogenation of X is greater than that of Y. Both X and Y react with HCI to give the same single C7H15Cl compound as the major product. What is the structure of X? • In cases where there is more than one answer, just draw one. 23 ▾ Sn [F ChemDoodleⓇ 146arrow_forwardThe heat of combustion of decahydronaphthalene(C10H18) is -6286 kJ/mol. The heat of combustion ofnaphthalene (C10H8) is -5157 kJ/mol. (In both casesCO2(g) and H2O(l) are the products.) Calculate the heat of hydrogenationand the resonance energy of naphthalene.arrow_forwardThe reaction of Hbr with 2-methylpropene produces 2-bromo-2-methylpropane. What is the structure of the carbocation formed during the reaction?arrow_forward
- (1) Predict the outcome of the addition of HBr to (a) trans-2-pentene, (b) 2-methyl-2-butene, and (c) 4-methylcyclohexene. How many isomers can be formed in each case? (2) Addition of HBr to 3,3-dimethyl-1-butene gives a mixture of two isomeric alkyl bromide products. Draw structures for the two products, and give a mechanistic explanation for their formation.arrow_forward4-methyl-3-hexanol was prepared by reacting an alkene with either hydroboration-oxidation or oxymercuration-reduction. Draw the structure of the alkene that was used to prepare the alcohol in highest yield. • You do not have to consider stereochemistry. • Indicate the method of preparation by drawing either BH3 (for . If there is more than one alkene that can be used for a given method, draw all of them. If either hydroboration-oxidation or oxymercuration-reduction can be used, just give the structures for one method. Separate structures with + signs from the drop-down menu. ● 981 -- 26224 ? ChemDoodle Y hydroboration-oxidation), or Hg (for oxymercuration-reduction), in a separate sketcher. Sn [1arrow_forwardYou are required to synthesize 2-bromopentane from the reaction between an alkene with HBr. Which alkene, 1-pentene or 2-pentene, should you react with HBr in order to get 2-bromopentane? Give an explanation.arrow_forward
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