Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition
9th Edition
ISBN: 9781292151229
Author: Wade, LeRoy G.
Publisher: PEARSON
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Textbook Question
Chapter 9, Problem 9.35SP
Show how you would synthesize the following compounds from acetylene and any other needed reagents:
- a. 6-phenylhex-1-en-4-yne
- b. cis-1-phenylpent-2-ene
- c. trans-1-phenylpent-2-ene
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Starting with cyclohexanone, show how to prepare these compounds. In addition to the given starting material, use any other organic or inorganic reagents as necessary.
a. Cyclohexanol
b. Cyclohexene
c. cis-1,2-Cyclohexanediol
d. 1-Methylcyclohexanol
e. 1-Methylcyclohexene
f. 1-Phenylcyclohexanol
g. 1-Phenylcyclohexene
h. Cyclohexene oxide
i. trans-1,2-Cyclohexanediol
What stereoisomers are formed in the following reactions? Which stereoisomer is the major product? a. the acid-catalyzed dehydration of 1-pentanol to 2-pentene b. the acid-catalyzed dehydration of 3,4-dimethyl-3-hexanol to 3,4-dimethyl-3-hexene
Which of the following compound would yield trialkylborane shown below when
treated with BH3 THF?
a. 2-methylbut-2-ene
b. 2-methylbut-1-ene
c. 3-methylbut-1-yne
d. 3-methylbut-1-ene
Clear my choice
Chapter 9 Solutions
Organic Chemistry Plus Masteringchemistry With Pearson Etext, Global Edition
Ch. 9.1 - a. Count the elements of unsaturation in...Ch. 9.2 - Prob. 9.2PCh. 9.4B - What reaction would acetylene likely undergo if it...Ch. 9.6 - Prob. 9.4PCh. 9.6 - Predict the products of the following acid-base...Ch. 9.7A - Solved Problem9-1 showed the synthesis of...Ch. 9.7A - Show how you might synthesize the following...Ch. 9.7B - Prob. 9.8PCh. 9.7B - Show how you would synthesize...Ch. 9.8 - When 2,2-dibromo-1-phenylpropane is heated...
Ch. 9.8 - When 2,2-dibromo-1-phenylpropane is heated...Ch. 9.9C - Show how you would convert a. oct-3-yne to...Ch. 9.9C - The fragrance of (Z)-1-phenylhex-2-en-1-ol...Ch. 9.9D - In the addition of just 1 mole of bromine to 1...Ch. 9.9E - Propose a mechanism for the entire reaction of...Ch. 9.9E - Predict the major product(s) of the following...Ch. 9.9E - Propose a mechanism for the reaction of pent-1-yne...Ch. 9.9E - Show how hex-1-yne might be converted to a....Ch. 9.9F - When pent-2-yne reacts with mercuric sulfate in...Ch. 9.9F - Prob. 9.20PCh. 9.9F - Prob. 9.21PCh. 9.9F - Prob. 9.22PCh. 9.10A - Predict the product(s) you would expect from...Ch. 9.10B - Prob. 9.24PCh. 9.10B - Prob. 9.25PCh. 9 - Prob. 9.26SPCh. 9 - Give common names for the following compounds. a....Ch. 9 - Prob. 9.28SPCh. 9 - Prob. 9.29SPCh. 9 - Using cyclooctyne as your starting material, show...Ch. 9 - Prob. 9.31SPCh. 9 - Prob. 9.32SPCh. 9 - Predict the products of reaction of pent-1-yne...Ch. 9 - Show how you would accomplish the following...Ch. 9 - Show how you would synthesize the following...Ch. 9 - Predict the products formed when CH3CH2C C : Na+...Ch. 9 - Prob. 9.37SPCh. 9 - Prob. 9.38SPCh. 9 - When compound Z is treated with ozone, followed by...Ch. 9 - Show how you would convert the following starting...Ch. 9 - The following functional-group interchange is a...Ch. 9 - Using any necessary inorganic reagents, show how...Ch. 9 - Prob. 9.43SP
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- 7) You want to synthesize 3-methyl-2-pentene from 2-chloro-3-methylpentane. Which reagent would you use? a. HCI, heat b. NH:(aq), 25°C c. CH:CO2NA, CH:CO2H, heat d. CH3CH2ONA, CH3CH2OH, heat e. CН:CH2ОН, heatarrow_forwardAlkyl halide can be prepared from the addition of H-X to alkenes. Identify the product in the reaction. H-Br Select one: a. 1,2-dibromo-2-methylpropane b. 1-bromo-2-methylpropane c. t-butyl bromide (or 2-bromo-2-methylpropane) d. 2-methylpropanearrow_forward2) The reaction shown will form which of the following? a. An alkyne b. An aldehyde c. A diol d. A ketone e. A carboxylic acid 1) 03, CH₂Cl₂, -78°C 2) H₂O₂arrow_forward
- Select the best reagent expected to convert 3-heptyne to cis-3-heptene. A. NaNH2, NH3 B. Na, NH3 C. H2, Lindlar’s catalyst D. Both A and C E. Both B and Carrow_forwardWhich of the alkyl chlorides listed below undergoes dehydrohalogenation in the presence of a strong base to give 2-pentene as the only alkene product? Select one: A. 1-chloropentane B. 3-chloropentane C. 2-chloropentane D. 1-chloro-2-methylbutane Which of the following is the most stable species? Select one: CH3 A. о в. H3C CH3 O D.arrow_forwardNitration of chlorobenzene gives A. o - chloronitrobenzene B. p - chloronitrobenzene C. m – chloronitrobenzene D. A and B BO DO CO A Oarrow_forward
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- Draw the major products obtained from the reaction of one equivalent of HCl with the following compounds. For each reaction, indicate the kinetic andthermodynamic products. a. 2,3-dimethyl-1,3-pentadiene b. 2,4-dimethyl-1,3-pentadienearrow_forward8. Write an equation representing each of the following reactions: a. 1-Heptene+H2O (H+) b. 3-Heptene+H2 c. 2-Methyl-2-hexene+HCI d. 3-Methyl-1,4-cyclohexadiene+C12 e. 2,4-Heptadiene+Br2 f. 3-Methylcyclopentene+H2O (H+)arrow_forward1. The alkene mixture obtained on dehydration of 2,2-dimethylcyclohexanol contains a significant amount of 1,2-dimethylcyclohexene a. Draw the structure of 1,2-dimethylcyclohexene b. Show a mechanism for the formation of this alkene product c. Draw the structures and give the names of any other alkene products, explaining how they could arise from the dehydration reactionarrow_forward
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