Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 7.10C, Problem 7.20P
(a)
Interpretation Introduction
To determine: The substitution and elimination products from the given reaction.
Interpretation: The substitution and elimination products from the given reaction are to be given.
Concept introduction: Substitution reactions are the reactions in which there is a replacement of an atom or a
Elimination reactions are the reactions in which
(b)
Interpretation Introduction
To determine: The substitution and elimination products from the given reaction.
Interpretation: The substitution and elimination products from the given reaction are to be given.
Concept introduction: Substitution reactions are the reactions in which there is a replacement of an atom or a functional group by another atom or a functional group.
Elimination reactions are the reactions in which alkenes are prepared. In this, two substituents are eliminated by either one step or two step mechanism.
(c)
Interpretation Introduction
To determine: The substitution and elimination products from the given reaction.
Interpretation: The substitution and elimination products from the given reaction are to be given.
Concept introduction: Substitution reactions are the reactions in which there is a replacement of an atom or a functional group by another atom or a functional group.
Elimination reactions are the reactions in which alkenes are prepared. In this, two substituents are eliminated by either one step or two step mechanism.
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Identify the substitution products that form when 2-bromo-2-methylpropane is dissolved in a mixture of 80% ethanol and 20% water.
a. Explain why the same products are obtained when 2-chloro-2-methylpropane is dissolved in a mixture of 80% ethanol and 20% water.
Give the main organic product that would form after the
following reaction.
OMe
OMe
H₂O
H*
Which reaction would have a reaction energy diagram like the one shown below:
Reaction Coordinate
a. Nucleophilic substitution reaction of methyl bromide with sodium hydroxide to give methanol
ob.Combination of methyl radical and a bromine atom to give methyl bromide
c. Electrophilic addition of HBr to propene to give 2-bromopropane
od. Homolysis of Bra using heat to give 2 free bromine atoms
Energy
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
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- Wittig reactions with the following -chloroethers can be used for the synthesis of aldehydes and ketones. (a) Draw the structure of the triphenylphosphonium salt and Wittig reagent formed from each chloroether. (b) Draw the structural formula of the product formed by treating each Wittig reagent with cyclopentanone. Note that the functional group is an enol ether or, alternatively, a vinyl ether. (c) Draw the structural formula of the product formed on acid-catalyzed hydrolysis of each enol ether from part (b).arrow_forwardAlcohols are important for organic synthesis, especially in situations involving alkenes. The alcohol might be the desired product, or the OH group might be transformed into another functional group via halogenation, oxidation, or perhaps conversion to a sulfonic ester derivative. Formation of an alcohol from an alkene is particularly powerful because conditions can be chosen to produce either the Markovnikov or non-Markovnikov product from an unsymmetrical alkene. Using your reaction roadmap as a guide, show how to convert 4-methyl-1-pentene into 5-methylhexanenitrile. You must use 4-methyl-1-pentene and sodium cyanide as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.arrow_forwarduo 9:0A Asiacell I. 02:48 المتبقي متعد د الخيارات Which alkyl halide would react the fastest under substitution conditions with HO-? 2-bromo-2-methylpentane O 2-bromo-3-methylpentane 1-bromo-2,2-dimethylpentane 2-bromopentane 1-bromo-4-methylpentane O 1 of 5arrow_forward
- . Which of the following can be both formed from bromoethane and converted directly into ethanal? CH3CH2Br → X → CH3CHO a. CH3CH2OH b. CH3OCH3 c. CH3COOH d. H2C=CHBrarrow_forwardWhat 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-hexenearrow_forwardWhich of the following alkyl halides undergoes an SN2 reaction with sodium methylthiolate, NaSCH3? to. ethyl iodide b. methyl iodide c. 2-bromopropane d. tert-butyl chloridearrow_forward
- X Upon ozonolysis, Compound X produces two compounds: Compound Y and Compound Z. Compound Y can also be prepared from the following synthetic route: PCC 1. R₂BH, THF 1. Mg. Et₂O PCC Compound Y 2. CH₂Cl₂ 2. NaOH, HO CH₂Cl₂ 3. H₂O* From this information, draw the structures of Compounds X, Y, and Z. For Compounds X and Z, different substituents are possible. For grading purposes, just use hydrogens as the substituents. Br مرد →] ►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_forwardCyclohexene (an alkene) is mixed with potassium permanagnate solution (KMnO4). What do you expect to observe? A. The mixture will turn purple as the permanganate is reduced by the alkene. B. The purple colour will disappear as the permanganate is reduced by the alkene. C. Nothing. Permanganate does not react with alkenes. D. The purple colour will disappear as the permanganate is oxidised by the alkene.arrow_forward
- Functional groups such as alkynes react the same in complex molecules as they do in simpler structures. The following example of alkyne reaction were taken from syntheses carried out in the research group of E. J. Corey at Harvard University. You can assume that the reactions listed involve only the alkyne, not any of the functional groups present in the molecules. Draw the expected products for the following reaction .arrow_forward43. Identify the reagent that will produce the following brominated product in greatest amount. Br A. Br2/uv B. Br2/FeBr3 C. NBS D. B12/CC14 44. Under acidic condition, which of the following compounds can not be oxidized by KMnO4. A. toluene B. 2-butene C. methylcyclohexane D. 2-butyne 45. What alkene product can be produced from the reaction of 2-hexyne with Lindlar's catalyst? A. cis-2-Hexene B. trans-2-Hexene C. Hexane D. A and Barrow_forwardWhich of the following compounds would be used to prepare the alkene shown below by the Wittig reaction? A. cyclohexyl bromide/propanal B. cyclohexanone/ethyl bromide C. cyclohexyl bromide/isopropyl bromide D. cyclohexanone/ethanalarrow_forward
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