Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Question
Chapter 7.14B, Problem 7.26P
Interpretation Introduction
Interpretation: The reaction of
Concept introduction: The elimination reaction is the organic reaction in which two substituents are removed from the organic molecule in one step or two steps. The two mechanisms of the elimination reaction are the E1 and E2 mechanisms.
In E2 mechanism, the elimination takes place in one step.
To determine: The reaction of
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
The reaction of 1-
methylcyclopentene with
mercuric trifluoroacetate in
ethanol followed by reduction
with sodium borohydride gives
1-ethoxy-1-
methylcyclopentane.
The -OH peak in the IR shows
up at 1700 cm-1 as a sharp
peak.
(S)-2-bromohexane is the
product of the reaction of
(S)-2-hexanol with PBr3.
The 1H NMR spectrum of 1-
pentanol will show a peak for
the H atom of the -OH group
at 10 ppm delta.
A tosylate is a great protecting
group for an alcohol.
The Williamson ether synthesis
is an SN2 reaction of an
alkoxide ion with a primary
alkyl halide.
Thionyl chloride converts
ketones into alkyl halides.
In an oxidation reaction, the
oxygen content of our organic
molecule decreases.
✓ [Choose ]
False
True
[Choose ]
[Choose ]
[Choose ]
[Choose ]
[Choose ]
[Choose ]
[Choose ]
Although there are nine stereoisomers of 1,2,3,4,5,6-hexachlorocyclohexane, one stereoisomer reacts 7000 times more slowly than any of the others in an E2 elimination. Draw the structure of this isomer and explain why this is so.
Show how you would synthesize the pure (S) enantiomer of the product, still starting with (R)-butan-2-ol and anyreagents you need.
Chapter 7 Solutions
Organic Chemistry (9th Edition)
Ch. 7.3A - Prob. 7.1PCh. 7.3A - Prob. 7.2PCh. 7.3B - Draw five more compounds of formula C4H6NOC1.Ch. 7.3B - For each of the following molecular formulas,...Ch. 7.4 - Give the systematic (IUPAC) names of the following...Ch. 7.5B - The following names are all incorrect. Draw the...Ch. 7.5B - Prob. 7.8PCh. 7.5B - a. How many stereogcmc double bonds are in...Ch. 7.6 - Teflon-coated frying pans routinely endure...Ch. 7.7B - Prob. 7.11P
Ch. 7.8B - Use the data in Table7-2 to predict the energy...Ch. 7.8C - Prob. 7.13PCh. 7.8E - Explain why each of the following alkenes is...Ch. 7.8F - Prob. 7.15PCh. 7.10 - Prob. 7.16PCh. 7.10A - SN1 substitution and E1 elimination frequently...Ch. 7.10C - Prob. 7.18PCh. 7.10C - Prob. 7.19PCh. 7.10C - Prob. 7.20PCh. 7.11 - Prob. 7.21PCh. 7.11 - Prob. 7.22PCh. 7.12 - Prob. 7.23PCh. 7.12 - Prob. 7.24PCh. 7.13 - Prob. 7.25PCh. 7.14B - Prob. 7.26PCh. 7.14B - Make models of the blowing compounds, and predict...Ch. 7.15 - Prob. 7.28PCh. 7.15 - Prob. 7.29PCh. 7.15 - Prob. 7.30PCh. 7.15 - Prob. 7.31PCh. 7.16 - Predict the major and minor elimination products...Ch. 7.17B - Predict the products and mechanisms of the...Ch. 7.18 - Propose mechanisms for the following reactions.Ch. 7.18 - Prob. 7.35PCh. 7.19B - The dehydrogenation of butane to trans-but-2-ene...Ch. 7.19B - Prob. 7.37PCh. 7.19B - Prob. 7.38PCh. 7.19B - Prob. 7.39PCh. 7 - Prob. 7.40SPCh. 7 - Prob. 7.41SPCh. 7 - Prob. 7.42SPCh. 7 - Prob. 7.43SPCh. 7 - Prob. 7.44SPCh. 7 - Prob. 7.45SPCh. 7 - Prob. 7.46SPCh. 7 - The energy difference between cis- and...Ch. 7 - Prob. 7.48SPCh. 7 - Prob. 7.49SPCh. 7 - Prob. 7.50SPCh. 7 - What halides would undergo E2 dehydrohalogenation...Ch. 7 - Prob. 7.52SPCh. 7 - Prob. 7.53SPCh. 7 - Write a balanced equation for each reaction,...Ch. 7 - Prob. 7.55SPCh. 7 - Using cyclohexane as your starting material, show...Ch. 7 - Show how you would prepare cyclopentene from each...Ch. 7 - Prob. 7.58SPCh. 7 - E1 eliminations of alkyl halides are rarely useful...Ch. 7 - Prob. 7.60SPCh. 7 - Propose mechanisms for the following reactions....Ch. 7 - Prob. 7.62SPCh. 7 - Prob. 7.63SPCh. 7 - Prob. 7.64SPCh. 7 - Prob. 7.65SPCh. 7 - Prob. 7.66SPCh. 7 - Prob. 7.67SPCh. 7 - Prob. 7.68SPCh. 7 - Prob. 7.69SPCh. 7 - Explain the dramatic difference in rotational...Ch. 7 - One of the following dichloronorbornanes undergoes...Ch. 7 - A graduate student wanted to make...Ch. 7 - Prob. 7.73SPCh. 7 - Prob. 7.74SPCh. 7 - Prob. 7.75SPCh. 7 - Prob. 7.76SP
Knowledge Booster
Similar questions
- Cis-1-bromo-4-isopropylcyclohexane undergoes E2 elimination, with sodium hydroxide, 5000 times faster than does trans-1-bromo-4-isopropylcyclohexane. Fully explain this reactivity difference using mechanisms which clearly show the transition state. You should draw both of these isomers in the chair form.arrow_forwardThe reaction of (2S)-2-chloro-3-methylpentane with sodium iodide yields two products: (2R)-2-iodo-3-methylpentane and racemic 3-iodo-2-methylpentane. Account for the formation of each of these two products. For each product, you should show how it is formed and what that tells you about the mechanism of that specific reaction.arrow_forwardDoes the reaction of S-2-bromobutane with sodium hydroxide produce a racemic mixturearrow_forward
- Show how the dehalogenation of (1R,2R)-1,2-dibromo-1,2-diphenyl ethane with zinc affords cis-stilbene. Show the mechanism with pictures.arrow_forwardThe tosylate of (2R,3S)-3-phenyl-2-butanol undergoes E2 elimination on treatment with sodium ethoxide to yield (Z)-2-phenyl-2-butene. Choose the incorrect Newman projections required for transition state of the reaction. Select all that are correctarrow_forwardIn the reaction of S-2-bromobutane with sodium hydroxide the product will be a racemic mixture. True Falsearrow_forward
- The isomer of 1,2,3,4,5,6-hexachlorocyclohexane shown undergoes E2 elimination 7000 times more slowly than any of its steroisomers. Explain this observation.arrow_forwardConsider the E1 reaction of 3-bromo-2-cyclohexyl-butane. How many elimination products are possible? Include (E)/(Z) isomers as separate products.arrow_forwardThe p-toluenesulfonate derived from (R)-2-octanol and p-toluenesulfonyl chloride was allowed to react with sodium benzenethiolate (C6H5SNa). Give the structure, including stereochemistry and the appropriate R or S descriptor, of the product.arrow_forward
- Arrange the following substrates in order of their increasing SN2 reactivity with KCN: bromoethane, 1-chloro-3,3-dimethylpentane, 1-chloro-2,2-dimethylpentane, and 2-bromo-2-methylpentane.arrow_forwardAcid-catalysed dehydration of 2,2-dimethylcyclohexanol yields, in part, isopropylidenecyclopentane. isopropylidenecyclopentane Draw structural formulas for the two carbocation intermediates in this reaction. • You do not have to consider stereochemistry. • Do not include counter-ions, e.g., Na*, 1, in your answer. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures using the → sign from the drop-down menu.arrow_forwardComplete the synthesis of 1-((15,2S, 3R, 6R)-6-methoxy-2,3-dimethylcyclohexyl)ethan-1-one + enantiomer from the starting material given ((1E,3Z)-1-methoxypenta-1,3-diene). You must list out all reagents/solvents used and draw the intermediate structures. You do NOT have to draw the mechanisms. Hint: the stereochemistry is very important. 2 + Enarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning