Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 10, Problem 46P
For each of the following
- a. 3-bromo-2,2,3-trimethylpentane
- b. 3-bromo-2,3-dimethylpentane
- c. 4-bromo-2,2,3,3-tetramethylpentane
- d. 3-bromo-3,4-dimethylhexane
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
For each of the following alkyl halides, indicate the stereoisomer that would be obtained in greatest yield in an E2 reaction.
a. 3-bromo-2,2,3-trimethylpentane
b. 4-bromo-2,2,3,3-tetramethylpentane
c. 3-bromo-2,3-dimethylpentane
d. 3-bromo-3,4-dimethylhexane
1. Which molecule reacts fastest with ethanol by SN1 mechanism?
a. 1-bromopentane
b. 3-bromopentane
c. 2-bromo-2-methylbutane
d. 1-bromo-2,2-dimethylpropane
Which of these alkenes will form propanone on the ozonolysis and will release the LEAST amount of heat on the catalytic hydrogenation.
A. 2-methyl-1-pentene
B. 2-methyl-2-pentene
C. 4-methyl-2-pentene
D. 4-methyl-1-pentene
Chapter 10 Solutions
Organic Chemistry
Ch. 10.2 - Prob. 1PCh. 10.2 - Prob. 2PCh. 10.2 - Prob. 3PCh. 10.2 - Prob. 4PCh. 10.3 - Four alkenes are formed from the E1 reaction of...Ch. 10.3 - If 2-fluoropentane could undergo an E1 reaction,...Ch. 10.3 - Prob. 7PCh. 10.3 - Propose a mechanism for the following reaction:Ch. 10.4 - Prob. 9PCh. 10.4 - What products will be obtained from the El...
Ch. 10.4 - Prob. 11PCh. 10.5 - Prob. 12PCh. 10.6 - Prob. 14PCh. 10.7 - Why do cis-1-bromo-2-ethylcyclohexane and...Ch. 10.7 - Which isomer reacts more rapidly in an E2...Ch. 10.7 - Prob. 18PCh. 10.8 - Prob. 19PCh. 10.8 - Prob. 20PCh. 10.9 - Prob. 21PCh. 10.9 - Explain why only a substitution product and no...Ch. 10.9 - Prob. 23PCh. 10.9 - Prob. 24PCh. 10.9 - Prob. 25PCh. 10.9 - a. Explain why 1-bromo-2,2-dimethylpropane has...Ch. 10.10 - A small amount of another organic product is...Ch. 10.10 - What is the best way to prepare the following...Ch. 10.10 - Prob. 29PCh. 10.10 - Prob. 30PCh. 10.10 - Why is a cumulated diene not formed in the...Ch. 10.10 - What product is obtained when the following...Ch. 10.11 - Prob. 33PCh. 10.11 - Prob. 34PCh. 10 - Draw the major product obtained when each of the...Ch. 10 - Prob. 36PCh. 10 - a. Indicate how each of the following factors...Ch. 10 - Prob. 38PCh. 10 - A chemist wanted to synthesize the...Ch. 10 - Prob. 40PCh. 10 - Prob. 41PCh. 10 - Prob. 42PCh. 10 - Starting with an alkyl halide, how could the...Ch. 10 - Indicate which species in each pair gives a higher...Ch. 10 - Prob. 45PCh. 10 - For each of the following alkyl halides, indicate...Ch. 10 - Prob. 47PCh. 10 - When 2-bromo-2,3-dimethylbutane reacts with a...Ch. 10 - Prob. 49PCh. 10 - When the following compound undergoes solvolysis...Ch. 10 - cis-1-Bromo-4-tert-butylcyclohexane and...Ch. 10 - Draw the substitution and elimination products.Ch. 10 - Prob. 53PCh. 10 - Prob. 54PCh. 10 - Which of the following hexachlorocyclohexanes is...Ch. 10 - Explain why the rate of the reaction of...Ch. 10 - Prob. 57PCh. 10 - Two elimination products are obtained from the...Ch. 10 - Draw the structures or the product of the obtained...Ch. 10 - How could you prepare the following compounds from...Ch. 10 - cis-4-Bromocyclohexanol and...Ch. 10 - Prob. 62PCh. 10 - Prob. 63P
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Choose the two alkyl bromides and the hydrogenation method that must be used to synthesize these alkenes from acetylene. Enter your answer as two letters in alphabetical order, followed by a number; i.e. ac2, not ca2. Do not use punctuation. Alkyl Halides a. CH3CH2Br b. CH3(CH2)4Br c. CH3(CH2)5Br d. CH3(CH2)¿Br e. CH3(CH2)¬Br f. CH3(CH2)gBr g. CH3(CH2)12Br Hydrogenation Method 1. H2, Lindlar's catalyst 2. Na, NH3 (I) Alkene #1: CH3 H3C bb1 Alkene #2: H3C. CH3 df1arrow_forwardChoose the two alkyl bromides and the hydrogenation method that must be used to synthesize these alkenes from acetylene. Enter your answer as two letters in alphabetical order, followed by a number; i.e. ac2, not ca2. Do not use punctuation. Alkyl Halides a. CH3CH₂Br b. CH3(CH₂)4Br c. CH3(CH2)sBr d. CH3(CH₂) Br e. CH3(CH₂)7Br f. CH₂(CH₂) Br g. CH3(CH₂)12Br Hydrogenation Method 1. H₂, Lindlar's catalyst 2. Na, NH3 (1) CH3 Alkene #1: H₂C Alkene #2: H₂C CH3arrow_forwardA terminal alkyne (RC=CH) is exposed to excess HBr. What rule should be followed to determine the placement of the halogen atoms in the product? A. Markovnikov rule O B. Hofmann's rule O C. Zaitzev's rule D. Anti-Markovnikov rulearrow_forward
- Which of the following alkyl halide will emit green flash of flame when a solution was dipped in copper wire and heated in flame? I. iodobenzene II. 2-chloropropane III. 1,2-dichlorohexane IV. 1-bromo-2-methyl-cyclopentane I, II, and III only O I, Il and IV only All of the above None of the above O II, III and IV onlyarrow_forward57. The order of decreasing ease of dehydrohalogenation OCH₂C I. >-CH2CH2CI A. I>II>III>IV B. CH3CH₂CHCICH3 C. II. CHOHCH₂CH3 D. CH3CHBRCH₂CH3 CH₂CH2C1 B. III>II>I>IV 58. Which of the following reactions will produce the highest percentage yield of 1-butene. OH A. CH3CH₂CH(N* (CH3)3)CH3 alc. KOH conc. H₂SO4 heat NaOC₂H5 III. C₂H5OH of the following compounds is: CH2CH₂CI CH₂CH₂C1 CH₂ -CH₂CH2CI C. III>IV>II> I IV. D. IV>III>II>Iarrow_forwardChoose the two alkyl bromides and the hydrogenation method that must be used to synthesize these alkenes from acetylene. Enter your answer as two letters in alphabetical order, followed by a number; i.e. ac2, not ca2. Do not use punctuation. a. CH3 CH₂ Br e. CH3 (CH₂)7 Br b. CH3 (CH₂)4 Br f. CH3 (CH2)8 Br c. CH3 (CH2)5Br g. CH3 (CH2) 12 Br d. CH3 (CH₂)6 Br Hydrogenation Method 1. H₂, Lindlar's catalyst 2. Na, NH3 (1) Alkene #1: Reagents available H₂C Alkene #2: H3C. CH3 CH3arrow_forward
- Choose the two alkyl bromides and the hydrogenation method that must be used to synthesize these alkenes from acetylene. Enter your answer as two letters in alphabetical order, followed by a number; i.e. ac2, not ca2. Do not use punctuation. a. CH3 CH₂ Br e. CH3 (CH₂)7 Br b. CH3 (CH2)4 Br f. CH3 (CH₂)8 Br c. CH3 (CH₂)5 Br g. CH3 (CH2) 12 Br d. CH3 (CH₂)6 Br Hydrogenation Method 1. H₂, Lindlar's catalyst 2. Na, NH3 (1) Alkene #1: H3C Reagents available Alkene #2: H3C CH3 CH3arrow_forward2. Which of the following alkynes will form only 1 product in acid-catalyzed hydration? a. 2-pentyne b. 3-hexyne c. 3-pentyne d. 1-hexyne 3. Which of the following statements best describes the general reactivity of alkynes? a. An alkyne reacts as an electrophile and is, therefore, electron poor. b. Alkynes undergo electrophilic addition reactions just like alkenes. c. An alkyne reacts as an electrophile and is therefore electron-rich. d. An alkyne reacts as a nucleophile and is therefore electron-poor.arrow_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_forward
- Choose the two alkyl bromides and the hydrogenation method that must be used to synthesize these alkenes from acetylene. Enter your answer as two letters in alphabetical order, followed by a number; i.e. ac2, not ca2. Do not use punctuation. Alkyl Halides а. СHзCH2Br b. CH3(CH2)4Br c. CH3(CH2)5Br d. CH3(CH2)§Br e. CH3(CH2);Br f. CH3(CH2)¿Br g. CH3(CH2)12Br Hydrogenation Method 1. H2, Lindlar's catalyst 2. Na, NH3 (1) Alkene #1: CH3 H3C bb1 Alkene #2: H3C, CH3 df1arrow_forwardAs we will learn in Section 13.12, many antioxidants–compounds that prevent unwanted radical oxidation reactions from occurring–are phenols, compounds that contain an OH group bonded directly to a benzene ring. a. Explain why homolysis of the O–H bond in phenol requires considerably less energy than homolysis of the O–H bond in ethanol (362 kJ/mol vs. 438 kJ/mol). b.Why is the C–O bond in phenol shorter than the C–O bond in ethanol?arrow_forwardpart 2 [References] Draw the final organic product of this series of reactions. 1. CH;CH2COCI, AICI3 2. Br2, CH3CO2H 3. K* tBuo 4. OsO, then NaHSO3 5. H2Cro4 • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Do not draw organic or inorganic by-products. C P. opy astearrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY
Alcohols, Ethers, and Epoxides: Crash Course Organic Chemistry #24; Author: Crash Course;https://www.youtube.com/watch?v=j04zMFwDeDU;License: Standard YouTube License, CC-BY