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 9, Problem 98P
When 2-bromo-2,3-dimethylbutane reacts with a strong base, two
- a. Which of the bases (A, B, C, or D) would form the highest percentage of the highest percentage of the 1-alkene?
- b. Which would give the highest percentage of the 2-alkene?
- A. CH3CH2O–
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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, heat
When 2-bromo-2,3-dimethylbutane reacts with a strong base, two alkenes (2,3-dimethyl-1-butene and 2,3-dimethyl-2-butene) are formed.
a. Which of the bases (A, B, C, or D) would form the highest percentage of the 1-alkene?
b. Which would give the highest percentage of the 2-alkene?
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
Chapter 9 Solutions
Organic Chemistry, Books a la Carte Edition (8th Edition)
Ch. 9.1 - Prob. 3PCh. 9.1 - Does increasing the energy barrier for an SN2...Ch. 9.1 - Rank the following alkyl bromides from most...Ch. 9.1 - Prob. 8PCh. 9.2 - Prob. 9PCh. 9.2 - Prob. 10PCh. 9.2 - Prob. 11PCh. 9.2 - Prob. 12PCh. 9.2 - Which substitution reaction lakes place more...Ch. 9.2 - Prob. 15P
Ch. 9.2 - Prob. 17PCh. 9.3 - Prob. 18PCh. 9.4 - Prob. 19PCh. 9.5 - Draw the configuration(s) of the substitution...Ch. 9.5 - Which of the following reactions take place more...Ch. 9.7 - Prob. 22PCh. 9.7 - Prob. 23PCh. 9.7 - Prob. 24PCh. 9.7 - Prob. 25PCh. 9.8 - Four alkenes are formed from the E1 reaction of...Ch. 9.8 - If 2-fluoropentane could undergo an E1 reaction,...Ch. 9.8 - Prob. 28PCh. 9.8 - Propose a mechanism for the following reaction:Ch. 9.9 - Prob. 30PCh. 9.9 - What percentage of the reaction described in...Ch. 9.10 - Prob. 33PCh. 9.10 - Prob. 35PCh. 9.11 - Why do cis-1-bromo-2-ethylcyclohexane and...Ch. 9.11 - Which isomer reacts more rapidly in an E2...Ch. 9.11 - Prob. 38PCh. 9.12 - Prob. 39PCh. 9.12 - Prob. 40PCh. 9.12 - Prob. 41PCh. 9.12 - Explain why only a substitution product and no...Ch. 9.12 - a. Explain why 1-bromo-2,2-dimethylpropane has...Ch. 9.13 - Prob. 44PCh. 9.13 - Prob. 45PCh. 9.13 - What products will be obtained from the El...Ch. 9.13 - Prob. 47PCh. 9.13 - Prob. 48PCh. 9.13 - Prob. 49PCh. 9.13 - Why is a cumulated diene not formed in the...Ch. 9.13 - What product is obtained when the following...Ch. 9.13 - What products are formed from the following...Ch. 9.14 - Prob. 54PCh. 9.14 - Prob. 55PCh. 9.14 - Prob. 56PCh. 9.14 - Prob. 58PCh. 9.14 - Under which of the following reaction conditions...Ch. 9.15 - A small amount of another organic product is...Ch. 9.15 - What is the best way to prepare the following...Ch. 9.15 - Prob. 62PCh. 9.15 - What products (including stereoisomers, if...Ch. 9.16 - After a proton is removed from the OH group, which...Ch. 9.16 - Prob. 65PCh. 9.17 - Prob. 66PCh. 9 - Prob. 1PCh. 9 - Methoxychlor is an insecticide that was intended...Ch. 9 - Prob. 67PCh. 9 - Prob. 68PCh. 9 - Prob. 69PCh. 9 - Prob. 70PCh. 9 - Prob. 71PCh. 9 - Prob. 72PCh. 9 - Starting with cyclohexene, how can the following...Ch. 9 - Prob. 74PCh. 9 - The pKa of acetic acid in water is 4.76. What...Ch. 9 - Prob. 76PCh. 9 - Prob. 77PCh. 9 - Prob. 78PCh. 9 - Prob. 79PCh. 9 - Prob. 80PCh. 9 - Prob. 81PCh. 9 - Prob. 82PCh. 9 - Draw the major product obtained when each of the...Ch. 9 - Prob. 84PCh. 9 - a. Indicate how each of the following factors...Ch. 9 - Prob. 86PCh. 9 - A chemist wanted to synthesize the...Ch. 9 - Prob. 88PCh. 9 - Prob. 89PCh. 9 - Prob. 90PCh. 9 - Prob. 91PCh. 9 - Starting with an alkyl halide, how could the...Ch. 9 - Indicate which species in each pair gives a higher...Ch. 9 - Prob. 94PCh. 9 - Rank the following from most reactive to least...Ch. 9 - For each of the following alkyl halides, indicate...Ch. 9 - Prob. 97PCh. 9 - When 2-bromo-2,3-dimethylbutane reacts with a...Ch. 9 - Prob. 100PCh. 9 - When the following compound undergoes solvolysis...Ch. 9 - cis-1-Bromo-4-tert-butylcyclohexane and...Ch. 9 - Draw the substitution and elimination products.Ch. 9 - tert-Butyl chloride undergoes solvolysis in both...Ch. 9 - Prob. 105PCh. 9 - Prob. 106PCh. 9 - In which solventethanol or diethyl etherwould the...Ch. 9 - Prob. 108PCh. 9 - Two bromoethers are obtained from the reaction of...Ch. 9 - Prob. 110PCh. 9 - Prob. 111PCh. 9 - Prob. 112PCh. 9 - Which of the following hexachlorocyclohexanes is...Ch. 9 - Explain why the rate of the reaction of...Ch. 9 - Prob. 115PCh. 9 - Two elimination products are obtained from the...Ch. 9 - Draw the structures or the product of the obtained...Ch. 9 - How could you prepare the following compounds from...Ch. 9 - cis-4-Bromocyclohexanol and...Ch. 9 - Prob. 120PCh. 9 - Propose a mechanism for the following reaction:Ch. 9 - Prob. 122PCh. 9 - Prob. 123PCh. 9 - Prob. 124PCh. 9 - Prob. 125PCh. 9 - Predict the product for the following reaction and...Ch. 9 - Prob. 127PCh. 9 - Prob. 128PCh. 9 - When equivalent amounts of methyl bromide nod...Ch. 9 - Prob. 130PCh. 9 - The reaction of chloromethane with hydroxide ion...
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- 2. Name each alkyne. a. CH3CH₂CH₂C=CH b. CH3CH₂CH₂C=CCH3 3. Predict the product of the following reactions. a. CH = CCH3 + HCI b. CH CCH₂CH3 + O2arrow_forwardSelect 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_forwardDraw the organic products formed when cyclopentene is treated with each reagent. With some reagents, no reaction occurs. a.H2 + Pd-C b.H2 + Lindlar catalyst c.Na, NH3 d.CH3CO3H e.[1] CH3CO3H; [2] H2O, HO− f.[1]OsO4 + NMO; [2] NaHSO3, H2O g.KMnO4, H2O, HO− h.[1] LiAlH4; [2] H2O i. [1] O3; [2] CH3SCH3 j.(CH3)3COOH, Ti[OCH(CH3)2]4, (−)-DET k.mCPBA l.Product in (k); then [1] LiAlH4; [2] H2Oarrow_forward
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- Before you answer this question, please read the following important principle: If a carbocation is formed in the slow step of a reaction, the reactivity of the reactant will be greater if that carbocation is more stable. The question: Which of the following alkenes reacts fastest with HCI? I HỌC=CHCH,CH,CH, IV CH₂ CH₂CH₂ Select one: OA. I O B. II O C. IV O D. III H H II CH3 H₂C-C-CH=CH₂ H III H₂C. H H CH₂CHarrow_forwardDraw the product or products that will be obtained from the reaction of cis-2-butene and trans-2-butene with each of the following reagents. If a product can exist as stereoisomers, show which stereoisomers are formed. 1. HCl. 4.Br2 in CH2Cl2 7. H2O + H2SO4 2. BH3/THF, followed by HO-, H2O2, H2O 5. Br2 + H2O 8. CH3OH + H2SO4 3. a peroxyacid 6. H2 + Pd/Carrow_forwardDetermine the one or two steps it takes to get from the starting material to the product using reactions found in this chapter. a. H2C. OH H2C-C ÇH:-OH b. CH,-ÇH-CH2-CH-CH, ČH,-CH, CH: CH;-CH-CH,-ċ-CH, CH2-CH, Br c. CH;-CH,-c=CH; CH;-CH,-C-CH3 CH3 CH3arrow_forward
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