Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
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Textbook Question
Chapter 10, Problem 92P
A vicinal
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Complete the following reaction sequence with the missing major organic products.
CH,
NaOH
CH,CH,CH,CHCH,CHCH,CEN
H20
NaOH
H,0
CH,CH,
What is required to complete the following reaction?
O 1) PPH3=CH2
2)NaBH4
O H₂NNH2/KOH
O 1) CH3MgBr., ether
2) KOH
O NaOH/H₂0
H3C
0=
C
H₂
CH3
H3C
H₂
C
H₂
CH3
ОН
Type of reaction
1-Propanol is heated
Type of reaction
H+, Heat
IZ
+
t
1-
NaOH
Chapter 10 Solutions
Organic Chemistry, Books a la Carte Edition (8th Edition)
Ch. 10.1 - Why are NH3 and CH3NH2 no longer nucleophiles when...Ch. 10.1 - Explain the difference in reactivity between...Ch. 10.1 - Prob. 5PCh. 10.1 - Prob. 6PCh. 10.1 - Prob. 8PCh. 10.2 - Prob. 9PCh. 10.3 - Prob. 11PCh. 10.3 - Show how 1-propanol can be converted into the...Ch. 10.4 - Which of the following alcohols dehydrates the...Ch. 10.4 - Prob. 14P
Ch. 10.4 - Prob. 15PCh. 10.4 - Propose a mechanism for each of the following...Ch. 10.4 - Draw the product of each of the following...Ch. 10.4 - Explain why the following alcohols, when heated...Ch. 10.4 - What stereoisomers are formed in the following...Ch. 10.4 - Prob. 20PCh. 10.4 - What alcohol would you treat with phosphorus...Ch. 10.5 - Prob. 22PCh. 10.6 - What are the major products obtained when each of...Ch. 10.6 - Prob. 26PCh. 10.7 - Prob. 27PCh. 10.7 - Would you expect the reactivity of a five-membered...Ch. 10.7 - Prob. 29PCh. 10.7 - What products are obtained from the reaction of...Ch. 10.7 - Prob. 31PCh. 10.7 - Prob. 32PCh. 10.7 - Prob. 33PCh. 10.8 - Draw the mechanism for formation of the two...Ch. 10.8 - Prob. 35PCh. 10.8 - Prob. 36PCh. 10.8 - How do the major products obtained from...Ch. 10.8 - Explain why the two arene oxides in Problem 38...Ch. 10.8 - Which compound is more likely to be carcinogenic?Ch. 10.8 - Three arene oxides can be obtained from...Ch. 10.9 - Explain why the half-life (the time it takes for...Ch. 10.10 - Prob. 43PCh. 10.10 - Prob. 44PCh. 10.10 - Prob. 45PCh. 10.10 - Prob. 46PCh. 10.10 - Prob. 47PCh. 10.10 - Describe a synthesis for each of the following...Ch. 10.11 - Using an alkyl halide and a thiol as starting...Ch. 10.11 - The following three nitrogen mustards were studied...Ch. 10.11 - Why is melphalan a good cancer drug?Ch. 10.11 - Prob. 53PCh. 10.12 - Propose a mechanism for the following reaction:Ch. 10 - Prob. 55PCh. 10 - Which compound is more likely to be carcinogenic?Ch. 10 - Prob. 57PCh. 10 - Prob. 58PCh. 10 - When heated with H2SO4, both...Ch. 10 - What is the major product obtained from the...Ch. 10 - Write the appropriate reagent over each arrow.Ch. 10 - What alkenes would you expect to be obtained from...Ch. 10 - Prob. 63PCh. 10 - Prob. 64PCh. 10 - When deuterated phenanthrene oxide undergoes a...Ch. 10 - An unknown alcohol with a molecular formula of...Ch. 10 - Explain why the acid-catalyzed dehydration of an...Ch. 10 - Prob. 68PCh. 10 - Prob. 69PCh. 10 - Propose a mechanism for the following reaction:Ch. 10 - What product would be formed if the four-membered...Ch. 10 - Which of the following ethers would be obtained in...Ch. 10 - Using the given starting material any necessary...Ch. 10 - Prob. 74PCh. 10 - When 3-methyl-2-butanol is heated with...Ch. 10 - Draw structures for compounds AF.Ch. 10 - Propose a mechanism for each of the following...Ch. 10 - How could you synthesize isopropyl propyl ether,...Ch. 10 - When ethyl ether is heated with excess HI for...Ch. 10 - When the following seven-membered ring alcohol is...Ch. 10 - Ethylene oxide reacts readily with HO because of...Ch. 10 - Describe how each of the following compounds could...Ch. 10 - Propose a mechanism for each of the following...Ch. 10 - Triethylene glycol is one of the products obtained...Ch. 10 - Prob. 85PCh. 10 - Propose a mechanism for the following reaction:Ch. 10 - Prob. 87PCh. 10 - An ion with a positively charged nitrogen atom in...Ch. 10 - The following reaction takes place several times...Ch. 10 - Prob. 90PCh. 10 - Propose a mechanism for each of the following...Ch. 10 - A vicinal diol has OH groups on adjacent carbons....Ch. 10 - Prob. 93PCh. 10 - Prob. 94PCh. 10 - Two stereoisomers are obtained from the reaction...Ch. 10 - Propose a mechanism for each or the following...Ch. 10 - Triethylenemelamine (TEM) is an antitumor agent....
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- Complete the following reactions with the appropriate reagents or products. 1 mol HBr H₂C 2 H₂ Pd 2 mol HCI ECH ? H₂C BH₂ H₂O₂, H₂O -CH ₂arrow_forward8) Show how the following conversions might be accomplished, including all reagents and intermediates. Br Y. OHarrow_forward5. Describe an efficient synthesis of 1-methyl-1-cyclohexanol from cyclohexanol. Show the structure of the reagents, reactants and products from each step. Cyclohexanol -------> -----> 1-methyl-1-cyclohexanolarrow_forward
- Mixing cyclohexanol with phosphoric acid is an exothermic process, whereas the production of cyclohexene is endothermic. Construct an energy diagram showing the course of this reaction. Label the diagram with the starting alcohol, the oxonium ion (the protonated alcohol), the carbocation, and the product.arrow_forwardAldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second molecule of alcohol gives an acetal and a molecule of water. ROH, H+ OH OR Aldehyde/ketone Alcohol ROH, H+ Draw the structural formulas for the hemiacetal and the acetal formed between the following compounds: OH OH OR OR • Use the wedge/hash bond tools to indicate stereochemistry where it exists. + H₂Oarrow_forwardGive the product. NO ₂ 0 HNO ₂ H₂SO4arrow_forward
- Give the IUPAC name for each alcohol но сн CH,CHCCH,CH,CH3 (CH)½CHCH,CHCH,CH3 b. a. CH,CH,CH,OH HO. с. CH,CH,CH,CH, Draw the products formed when each alcohol is dehydrated with H2SO4. Use the Zaitsev rule to predict the major product when a mixture forms. OH он b. -CHCH,CH3 а. Он с. CH3CHCH2CH,CH;CH3arrow_forwardSynthesize the products by drawing out reagents and intermediates along the way.arrow_forwardName the following alcohol. O2-Bromo-4-ethylcyclopentanol 4-Ethyl-2-bromocyclopentanol O1-Ethyl-3-bromo-4-cyclopentanol O1-Bromo-4-ethyl-2-cyclopentanolarrow_forward
- Acetals are formed from the reaction of two alcohols with a carbonyl under acidic conditions. Acetal formation is faster with 1,2-ethanediol than with two methanol molecules. Choose the factor that explains the difference in reaction rates. A) The reaction with 1,2-ethanediol has a lower AH (enthalpy) of reaction. B) The reaction with 1,2-ethanediol has a higher AH (enthalpy) of reaction. C) The reaction with 1,2-ethanediol has a more favorable entropy of reaction.arrow_forward3. Complete the following intramolecular dehydration reactions for alcohols. Draw the structure of the product. Name the reactant and the product. a) Cy-C-CH-oH 18UC b) CHy CH-Cy-CHy 180C OH c) 180c 4. Complete the following intermolecular dehydration reactions for alcohols. Draw the structure of the product. Name the reactant and the product. a) CHy-CH-OH b) Ho SわふわSわ 5. Complete the following oxidation reactions for alcohols. Draw the structure of the product. Name the reactant and identify the type of compound formed in the product. a) hparrow_forwardProvide the major organic product of the following reaction. but-1-yne 1) Sia₂BH 2) H₂O₂, OH What is it called when an enol converts to a keto? A) Keto-enol isomerism B) Keto-enol tater tot-ism C) Keto-enol conversion D) Keto-enol tautomerismarrow_forward
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