Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 7, Problem 7.60SP
(a)
Interpretation Introduction
To determine: The mechanism and the reaction-energy diagram for the given reaction.
Interpretation: The mechanism and the reaction-energy diagram for the given reaction is to be drawn.
Concept introduction: The reaction-energy diagram is a graph of the progress of a
(b)
Interpretation Introduction
To determine: The mechanism and the reaction-energy diagram for the given reaction.
Interpretation: The mechanism and the reaction-energy diagram for the given reaction is to be drawn.
Concept introduction: The reaction-energy diagram is a graph of the progress of a chemical reaction versus the total energy of the system. The energy of the products would be higher than that of the reactants if the reaction is an endothermic reaction. The reaction, in which the energy is given off, is an exothermic reaction.
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Students have asked these similar questions
4. Which of the following reactions is NOT a method of preparation of alkylhalide?
A. addition of halogens to alkenes
B. replacement of the -OH in alcohol by a halide
C. dehydrohalogenation
of hydrocarbon
D. addition of hydrogen halide to alkene
5. In SN₂ reaction of alkylhalide(substrate) with NaOH(nucleophile), the rate of the reaction is tripled if the
concentration of:
A. Substrate and nucleophile are both doubled
B. Nucleophile is decreased by 1/3 and substrate doubled
C. Substrate is tripled and nucleophile doubled
D. Nucleophile is tripled
6. Arrange the following alkylhalide in order of decreasing reactivity in an SN₁ reaction:
I. CH3CH(Br)CH₂CH3
A. I>II>III>IV
II. CH3CH(C1)CH₂CH3 III. CICH₂CH₂CH₂CH3 IV. (CH3)2C(Br)CHCH3
D. IV>II>I>III
B. IV>III>II>I C. IV>I>II>III
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.
The product of the electrophilic addition of 3-methyl-2-hexene with propanol and
bromine will produce the following major product with the following in it's name:
O a. 2-ethyl ether and 3 bromine
O b. 2-ethyl ether and 4 bromine
O c. 2-ethyl ether and 2 bromine
O d. 3-ethyl ether and pentane
O e. 3-ethyl ether and 2 bromine
Which of the following alkenes will yield 3-bromo-3-methylpentane as the major
product upon addition of HBr?
IV
Ol only
Oll and II only
OiV only
Oll only
OAII of them
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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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
- The product of the electrophilic addition of 3-methyl-2-hexene with propanol and bromine will produce the following major product with the following in it's name: O a. 3-ethyl ether and 2 bromine O b. 2-ethyl ether and 3 bromine O c. 2-ethyl ether and 2 bromine O d. 3-ethyl ether and pentane O e. 2-ethyl ether and 4 brominearrow_forwardPick the reactant or solvent in each part that gives the faster elimination reaction.a. reaction of -OH with 1-chloro-1-methylcyclohexane or 1-chloro-3-methylcyclohexaneb. reaction of H2O with CH3CH(Cl)CH2CH3 or (CH3)2C(Cl)CH2CH3c. reaction of (CH3)3CCl with -OH in H2O or DMSOarrow_forward11. Predict the product when cis-3-methylcyclopentanol is treated with TsCl/pyridine, followed by sodium bromide. a. trans-1-bromo-3-methylcyclopentane b. cis-1-bromo-3-methylcyclopentane c. 1-methylcyclopentene d. 2-methylcyclopentene e. 3-methylcyclopentenearrow_forward
- Show how you would synthesize each compound from benzene, toluene, or phenol using the following reactions: Reactions 1. Halogenation 2. Nitration 3. Sulfonation 4. Friedel-Crafts acylation 5. Friedel-Crafts alkylation 6. Oxidation of methyl group 7. Reduction of nitro group • Choose the starting material from the drop-down list • Enter the number(s) of the desired reactions in the order that you wish to use them without commas between • If a reaction is used more than once, enter its number each time you wish to use it Compound 1: 5-chloro-2-methylbenzenesulfonic acid Starting material: toluene Reaction(s): 31 Compound 2: m-bromobenzoic acid Starting material: [benzene Reaction(s): Submit Answer Try Another Version 1 item attempt remainingarrow_forwardSynthesize each compound from toluene and any other organic or inorganic reagents. a. C6HSCH2BR b. C6HSCH2OC(CH3)3 -CHO с. O,N НООС -NO2 d. H,N.arrow_forwardWhich of the following reaction may have a different reaction mechanism compared to the others? a. Hydration b. Hydrohalogenation c. Halogenation d. Ether formationarrow_forward
- Give IUPAC names to the following molecules. CI a. b. b. b. C. d. Br CI- Draw all the products (alkyl halides) of the following reactions and classify them as primary, secondary, or tertiary a. OH X . Br Br Complete the following reactions by filling in the missing reagents. a. OH NBS hv OH hv, CC14 Br NBS ť Licu C. -MgBr CI → CI Br Brarrow_forwardProvide all products AND mechanisms for the following reactions (no transition states or energy diagrams required). Remember that substitution and elimination can compete in the right circumstances. A. CH3O DMSO Cl B. I HO DMFarrow_forwardThese reagents can produce ketones with alkynes A. BH3, THF, H2O2 B. KMnO4 C. O3 D. H2SO4, H2O, HgSO4arrow_forward
- 2. Propose a mechanism to account for the formation of this product. HO- H2SO4,Heatarrow_forward- How could the following changes in reaction conditions affect the rate of the reaction when isopropanol (IPA) reacts with 2-bromo-2-methylpentane? The concentration of the IPA is halved by adding petroleum ether as the solvent. b. The concentration of the bromoalkene is quadrupled. а.arrow_forwardAlkyl halides undergo elimination reactions to produce alkenes by the reacting with strong bases as shown in the following reaction (see image). In general, compounds where the halogen is axial (axial position) are much more reactive than those in which they are in the equatorial position. Taking the above into account: a. Which of the following compounds would give a faster elimination reaction: cis-1-bromo-2-tert-butylcyclohexane or trans-1-bromo-2-tert-butylcyclohexane? Draw the corresponding structures and clearly explain the choice.arrow_forward
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