All Matches
Solution Library
Expert Answer
Textbooks
Search Textbook questions, tutors and Books
Oops, something went wrong!
Change your search query and then try again
Toggle navigation
FREE Trial
S
Books
FREE
Tutors
Study Help
Expert Questions
Accounting
General Management
Mathematics
Finance
Organizational Behaviour
Law
Physics
Operating System
Management Leadership
Sociology
Programming
Marketing
Database
Computer Network
Economics
Textbooks Solutions
Accounting
Managerial Accounting
Management Leadership
Cost Accounting
Statistics
Business Law
Corporate Finance
Finance
Economics
Auditing
Ask a Question
Search
Search
Sign In
Register
study help
chemistry
organic chemistry
Questions and Answers of
Organic Chemistry
a. Indicate how each of the following factors affects an SN1 reaction: b. Indicate how each of the following factors affects an SN2 reaction: 1. The structure of the alkyl halide 2. The reactivity of
Which is a better nucleophile in methanol? a. H2O or HO- b. NH3 -NH2 c. H2O or H2S d. HO- or HS- e. I- or Br - f. Cl- Br-
For each of the pairs in Problem 34, indicate which is a better leaving group. In Problem 34 Which is a better nucleophile in methanol? a. H2O or HO- b. NH3 -NH2 c. H2O or H2S d. HO- or HS- e. I- or
What nucleophiles could be used to react with butyl bromide to prepare the following compounds?a. CH3CH2CH2CH2OHb. CH3CH2CH2CH2OCH3c. CH3CH2CH2CH2SHd. CH3CH2CH2CH2SCH2CH3e. CH3CH2CH2CH2NHCH3f.
Rank the following compounds in order of decreasing nucleophilicity:a.b. c. H2O and NH3 in methanol d. Br-, Cl-, I- in methanol
For each of the following reactions, give the substitution products; if the products can exist as stereoisomers, show what stereoisomers are obtained: a. (R)-2-bromopentane + high concentration of
Which reaction in each of the following pairs will take place more rapidly?a.b.c.d.
Which of the following compounds would you expect to be more reactive in an SN2 reaction?
In Section 10.11, we saw that S-adenosylmethionine (SAM) methylates the nitrogen atom of noradrenaline to form adrenaline, a more potent hormone. If SAM methylates an OH group on the benzene ring
For each of the following reactions, give the substitution products; if the products can exist as stereoisomers, show what stereoisomers are obtained: a. (2S,3S)-2-chloro-3-methylpentane + high
Give the substitution products obtained when each of the following compounds is added to a solution of sodium acetate in acetic acid. a. 2-chloro-2-methyl-3-hexene b. 3-bromo-1-methylcyclohexene
The rate of reaction of methyl iodide with quinuclidine was measured in nitrobenzene, and then the rate of reaction of methyl iodide with triethylamine was measured in the same solvent.a. Which
Only one bromoether (ignoring stereoisomers) is obtained from the reaction of the following alkyl dihalide with methanol:Give the structure of the ether.
Starting with cyclohexane, how could the following compounds be prepared? a. cyclohexyl bromide b. methoxycyclohexane c. cyclohexanol
For each of the following reactions, give the substitution products, assuming that all the reactions are carried out under SN2 conditions; if the products can exist as stereoisomers, show what
Indicate whether each of the following solvents is protic or aprotic: a. Chloroform (CHCl3) b. Diethyl ether (CH3CH2OCH2CH3) c. Acetic acid (CH3COOH) d. Hexane [CH3(CH2)4CH3]
Explain why tetrahydrofuran can solvate a positively charged species better than diethyl ether can.
Propose a mechanism for each of the following reactions:a.b.
Which of the following will react faster in an SN1 reaction?
Alkyl halides have been used as insecticides since the discovery of DDT in 1939. DDT was the first compound to be found that had a high toxicity to insects and a relatively low toxicity to mammals.
Explain why the following alkyl halide does not undergo a substitution reaction, regardless of the conditions under which the reaction is run:
For each of the following pairs of SN2 reactions, indicate which reaction occurs faster:a. CH3CH2Br + H2O or CH3CH2Br + HOb.c. d. CH3CH2Cl + I or CH3CH2Br + I
a. Explain why the reaction of an alkyl halide with ammonia gives a low yield of primary amine.b. Explain why a much better yield of primary amine is obtained from the reaction of an alkyl halide
Which of the alkyl halides is more reactive in an E2 reaction?a. CH3CH2CH2Br orb.c.d.
a. Determine the major product that would be obtained from an E2 reaction of each of the following alkyl halides (in each case, indicate the configuration of the product):1.2.3.b. Does the product
For each of the following alkyl halides, determine the major product that is formed when that alkyl halide undergoes an E1 reaction:a.b. c.
Why do cis-1-bromo-2-ethylcyclohexane and trans-1-bromo-2-ethylcyclohexane form different major products when they undergo an E2 reaction?
Which isomer reacts more rapidly in an E2 reaction, cis-1-bromo-4-tert-butylcyclohexane or trans-1-bromo-4-tert-butylcyclohexane? Explain your choice.
Give the substitution and elimination products for the following reactions, showing the configuration of each product:a.b. c. d. e. f.
List the following compounds in order of decreasing reactivity in an E2 reaction:
If the two reactions described in this section were E1 elimination reactions, what value would you expect to obtain for the deuterium kinetic isotope effect?
How would you expect the ratio of substitution product to elimination product formed from the reaction of propyl bromide with CH3O- in methanol to change when the nucleophile is changed to CH3S-?
Only a substitution product is obtained when the following compound is treated with sodium methoxide:Explain why an elimination product is not obtained.
Indicate whether the alkyl halides listed will give mostly substitution products, mostly elimination products, or about equal amounts of substitution and elimination products when they react with the
Draw a reaction coordinate diagram for the E2 reaction of 2-bromo-2,3-dimethylbutane with sodium tert-butoxide.
1-Bromo-2,2-dimethylpropane has difficulty undergoing either SN2 or SN1 reactions. a. Explain why. b. Can it undergo E2 and E1 reactions?
What other organic product will be formed when the alkyl halide used in the synthesis of butyl propyl ether is a. Propyl bromide? b. Butyl bromide?
How could the following ethers be prepared, using an alkyl halide and an alcohol?a.b. c. d.
Which compound, upon treatment with sodium hydride, would form a cyclic ether more rapidly?a.b.c.
How could you have prepared the target molecule in the preceding synthesis using 4-penten 1-ol as the starting material? Which synthesis would give you a higher yield of the target molecule?
Design a multistep synthesis to show how each of the following compounds could be prepared from the given starting material:a.b. c. d. H3CH2CH2CH2Br e. BrCH2CH2CH2CH2Br
Give the major product obtained when each of the following alkyl halides undergoes an E2 reactiona.b. c. d. e. f. g.
Give the major elimination product obtained from an E2 reaction of each of the following alkyl halides with hydroxide ion:a.b.c.d.e.f.
Give the major product obtained when the alkyl halides in Problem 29 undergo an E1 reaction.
a. Indicate how each of the following factors affects an E1 reaction:1. The structure of the alkyl halide 2. The strength of the base 3. The concentration of the base4. The solventb. Indicate how
Dr. Don T. Doit wanted to synthesize the anesthetic 2-ethoxy-2-methylpropane. He used ethoxide ion and 2-chloro-2-methylpropane for his synthesis and ended up with very little ether. What was the
Which reactant in each of the following pairs will undergo an elimination reaction more rapidly? Explain your choice.a.b.
For each of the following reactions, give the elimination products; if the products can exist as stereoisomers, indicate which isomers are obtained. a. (R)-2-bromohexane + high concentration of
Indicate which of the compounds in each pair will give a higher substitution/elimination ratio when it reacts with isopropyl bromide:a. Ethoxide ion or tert-butoxide ion b. -OCN or -SCN c. CI- or
Rank the following compounds in order of decreasing reactivity in an E2 reaction
Using the given starting material and any necessary organic or inorganic reagents, indicate how the desired compounds could be synthesized:a.b. CH3CH2CH=== CH2
When 2-bromo-2,3-dimethylbutane reacts with a base under E2 conditions, two alkenes (2,3-dimethyl-1-butene and 2,3-dimethyl- 2-butene) are formed.a. Which of the bases shown would give the highest
a. Give the structure of the products obtained from the reaction of each enantiomer of cis-1 chloro-2-isopropylcyclopentane witha high concentration of sodium methoxide in methanol.b. Are all the
Which alkyl halide would you expect to be more reactive in an E2 reaction?a.b.c.d.
Starting with cyclohexane, how could the following compounds be prepared? a. Trans-1,2-dichlorocyclohexane b. 2-cyclohexenol
The rate constant of an intramolecular reaction depends on the size of the ring (n) that is formed. Explain the relative rates of formation of the cyclic secondary ammonium ions.
cis-1-Bromo-4-tert-butylcyclohexane and trans-1-bromo-4-tert-butylcyclohexane both react with sodium ethoxide in ethanol to give 4-tert-butylcyclohexene. Explain why the cis isomer reacts much more
Cardura®, a drug used to treat hypertension, is synthesized as follows:Identify the intermediate (A), and show the mechanism for its formation. Also, show the mechanism for the conversion of A to
For each of the following reactions, give the elimination products; if the products can exist as stereoisomers, indicate which stereoisomers are obtained. a. (2S.3S-2-chIoro-3-methyIpcntane + high
Which of the following hexachlorocyclohexanes is the least reactive in an E2 reaction?
The rate of the reaction of 1-bromo-2-butene with ethanol is increased if silver nitrate is added to the reaction mixture. Explain.
For each of the following reactions, carried out under SN2/E2 conditions, give the products; if the products can exist as stereoisomers, show which stereoisomers are formed. a.
Two elimination products are obtained from the following E2 reaction:a. What are the elimination products? b. Which is formed in greater yield? Explain.
Three substitution products and three elimination products are obtained from the following reaction:Account for the formation of these products.
Three alkenes are formed from the E1 reaction of 3-bromo-2,3-dimethylpentane. Give the structures of the alkenes, and rank them according to the amount that would be formed. (Ignore stereoisomers.)
When the following stereoisomer of 2-chloro-1,3-dimethylcyclohexane reacts with methoxide ion in a solvent that encourages SN2/E2 reactions, only one product is formed:When the same compound reacts
For each of the following compounds, give the product that will be formed in an E2 reaction and indicate the configuration of the product: a. (1S,2S)-1-bromo-1,2-diphenylpropane b.
If 2-fluoropentane were to undergo an E1 reaction, would you expect the major product to be the one predicted by Zaitsev's rule? Explain.
Propose a mechanism for the following reaction:
For each of the following reactions, (1) indicate whether elimination will occur via an E2 or an E1 reaction, and (2) give the major elimination product of each reaction, ignoring
The rate law for the reaction of HO- with tert-butyl bromide to form an elimination product in 75% ethanol 25% water at 30 °C is the sum of the rate laws for the E2 and E1 reactions:rate = 7.1 ×
The observed relative reactivities of primary, secondary, and tertiary alcohols with a hydrogen halide are 3o> 2o> 1o.If secondary alcohols underwent an reaction rather than an reaction with a
What alcohol would you treat with phosphorus oxychloride and pyridine to form each of the following alkenes?a.b. c. CH3CH == CHCH2CH3 d.
Propose a mechanism for each of the following reactions:a.b. c.
Give the major product formed when each of the following alcohols is heated in the presence of H2SO4;a.b.c.d.e.f. CH3CH2CH2CH2CH2OH
Explain why methyl propyl ether forms both methyl iodide and propyl iodide when it is heated with excess HI.
Can HF be used to cleave ethers? Explain
Give the major products that would be obtained from heating each of the following ethers with HI:a. CH3CH == CHOCH2CH3b.c.d.e.f.
Draw the structure of the following compounds: a. 2-propyloxirane b. Cyclohexene oxide c. 2,2,3,3-tetramethyloxirane d. 2,3-epoxy-2-methylpentane
Why does the preceding reaction form two stereoisomers?
Give the major product of each of the following reactions:a.b. c. d.
Would you expect the reactivity of a five-membered ring ether such as tetrahydrofuran (Table 12.2) to be more similar to an epoxide or to a noncyclic ether?
Give the major product of each of the following reactions:a.b.c.d.
Draw all possible resonance contributors for the two carbocations in the preceding reaction. Use the resonance contributors to explain why 1-napthol is the major product of the reaction.
The existence of the NIH shift was established by determining the major product obtained from rearrangement of the following arene oxide, in which a hydrogen has been replaced bya deuterium:What
How would the major products obtained from rearrangement of the following arene oxides differ?
Which compound is more likely to be carcinogenic?b.
Explain why the two arene oxides in Problem 23a open in opposite directions.
Three arene oxides can be obtained from phenanthrene.a. Give the structures of the three phenanthrene oxides.b. What phenols can be obtained from each phenanthrene oxide?c. If a phenanthrene oxide
Using an alkyl halide and a thiol as starting materials, how would you prepare the following compounds?a. CH3CH2SCH2CH3b.c.d.
Finding that mustard gas interfered with bone marrow development caused chemists to look for less reactive mustard gases that might be used clinically. The following three compounds were studied:One
What alcohols would be formed from the reaction of ethylene oxide with the following Grignard reagents?a. CH3CH2CH2MgBrb.c.
How could the following compounds be prepared, using cyclohexene oxide as a starting material?a.b. c.
Why can a halide ion such as Br- react with a protonated primary alcohol, but not with a protonated primary amine?
What organometallic compound will be formed from the reaction of methylmagnesium SiCI4? chloride and (Hint: See Table 12.3.)
Muscalure is the sex attractant of the common housefly. Flies are lured to traps by filling them with fly bait containing both muscalure and an insecticide. Eating the bait is fatal.How could you
What alkyl halides would you utilize to synthesize the following compounds, using the organoborane shown?a. b. c.
Give two sets of alkyl bromide and alkene that could be used in a Heck reaction to prepare the following compound:
Give the product of each of the following reactionsa.b. c. d. e. f. g. h. i. j.
Indicate which alcohol will undergo dehydration more rapidly when heated with H2SO4.a.b.c.d.e.f.
Showing 14000 - 14100
of 15575
First
134
135
136
137
138
139
140
141
142
143
144
145
146
147
148
Last