EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Question
Chapter 22, Problem 34P
Interpretation Introduction
Interpretation:
The rate enhancement provided by the catalyst has to be calculated
Concept introduction:
- Catalyst: Substance which helps in increasing the rate of a particular reaction without getting consumed in the reaction.
- The rate enhanced by the catalyst can be calculated by,
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
H3C
CH3
H3C
NA C→XT
Br
Br₂
CH₂Cl₂
H3C
Electrophilic addition of bromine, Br₂, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic
intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH₂Cl₂.
CH3
Br
In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion
to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the
bromonium ion so that a product with anti stereochemistry is formed.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
Br
CH3
H3C
CH3
When 2-chloro-2-methylpropane, (CH3)3CCl, reacts with aqueous sodium hydroxide, the process is not a “concerted process”; instead a reactive intermediate, (CH3)3C+, is formed as a result of the first step of the reaction mechanism.
Explain why this happens.
Amantadine is effective in preventing infections caused by the influenza A virus and in
treating established illnesses. It is thought to block a late stage in the assembly of the
virus. Amantadine is synthesized by treating 1-bromoadamantane with acetonitrile in
sulfuric acid to give N-adamantylacetamide, which is then converted to amantadine.
CH,C=N
in H,SO,
Br
NHCCH3
NH2
1-Bromoadamantane
Amantadine
(a) Propose a mechanism for the transformation in Step 1.
(b) Describe experimental conditions to bring about Step 2.
Chapter 22 Solutions
EBK ORGANIC CHEMISTRY
Ch. 22.2 - Compare each of the mechanisms listed here with...Ch. 22.2 - Prob. 3PCh. 22.2 - Prob. 4PCh. 22.3 - a. Draw the mechanism for the following reaction...Ch. 22.5 - Prob. 7PCh. 22.5 - Propose a mechanism for the Co2+ catalyzed...Ch. 22.6 - Prob. 9PCh. 22.7 - Prob. 10PCh. 22.7 - Prob. 12PCh. 22.7 - Prob. 13P
Ch. 22.9 - Which of the following amino acid side chains can...Ch. 22.9 - Which of the following C-terminal peptide bonds is...Ch. 22.9 - Carboxypeptidase A has esterase activity as well...Ch. 22.10 - Arginine and lysine side chains fit into trypsins...Ch. 22.10 - Explain why serine proteases do not catalyze...Ch. 22.11 - If H2 18O is used in the hydrolysis reaction...Ch. 22.11 - Draw the pH-activity profile for an enzyme that...Ch. 22.12 - The pHactivity profile for glucose-6-phosphate...Ch. 22.12 - Prob. 23PCh. 22.13 - Draw the mechanism for the hydroxide ion-catalyzed...Ch. 22.13 - What advantage does the enzyme gain by forming an...Ch. 22.13 - Prob. 26PCh. 22.13 - Prob. 27PCh. 22.13 - Aldolase shows no activity if it is incubated with...Ch. 22 - Which of the following parameters would be...Ch. 22 - Prob. 29PCh. 22 - Prob. 30PCh. 22 - Prob. 31PCh. 22 - Indicate the type of catalysis that is occurring...Ch. 22 - The deuterium kinetic isotope effect (KH2O/KD2O)...Ch. 22 - Prob. 34PCh. 22 - Co2+ catalyzes the hydrolysis of the lactam shown...Ch. 22 - there are two kinds of aldolases. Class I...Ch. 22 - Prob. 37PCh. 22 - The hydrolysis of the ester shown here is...Ch. 22 - Prob. 39PCh. 22 - At pH = 12, the rate of hydrolysis of ester A is...Ch. 22 - 2-Acetoxycyclohexyl tosylate reacts with acetate...Ch. 22 - Proof that an imine was formed between aldolase...Ch. 22 - Prob. 43PCh. 22 - a. Explain why the alkyl halide shown here reacts...Ch. 22 - Triosephosphate isomerase (TIM) catalyzes the...
Knowledge Booster
Similar questions
- One frequently used method for preparing methyl esters is by reaction of carboxylic acids with diazomethane, CH2N2. The reaction occurs in two steps: (l) protonation of diazomethane by the carboxylic acid to yield methyldiazonium ion, CH3N2+, plus a carboxylate ion; and (2) reaction of the carboxylate ion with CH3N2+. (a) Draw two resonance structures of diazomethane, and account for step 1. (b) What kind of reaction occurs in step 2?arrow_forwardSubject: Organic Chemistry Topic: Synthesis of Aspirin Question: Show the reaction scheme and mechanism in the synthesis of aspirin.arrow_forwardPropose a mechanism for this example of chloromethylationarrow_forward
- Bromine reacts with alkenes in methanol according to the equation when this reaction was carried out with 4-tert-butylcyclohexene, only one isomer was formed with the molecular formula C12H23BrO (80% yield). Which of the following is the structure more reasonable for this compound? Explain your reasoning through a corresponding mechanism.arrow_forwardDescribe the product formed as a result of the reaction between cyclohexanone and 3-butene-2-one by also writing the mechanism of the reaction.arrow_forwardUnder milder temperatures than what is needed for dehydration, strong acids catalyze the self-condensation of 1-propyl alcohol to give di-n-propyl ether. The mechanism differs from that of today's reaction in that the protonated alcohol undergoes an Sn2 rather than an Sn1 reaction. Write the mechanism for the acid catalyzed condensation of ethyl alcohol to give diethyl ether. Make sure the mechanism includes protonation, Sn2, and deprotonation.arrow_forward
- CH3 Ph3P-CHCH3 H3C H3C Aldehydes and ketones are converted into alkenes by means of a direct nucleophilic addition called the Wittig reaction. In the reaction, a triphenylphosphorine ylide, also called a phosphorane, adds to an aldehyde/ketone to give a four-membered cyclic intermediate called an oxaphosphetane. The oxaphosphetane is not isolated but instead spontaneously decomposes to release triphenylphosphine oxide and an alkene. Ph3P-CHCH3 H3C The ylide is formed by reaction of triphenylphosphine, a good nucleophile, with a primary alkyl halide in an S 2 reaction, followed by deprotonation of the carbon with a strong base, such as butyllithium. The carbonyl carbon and the carbon originally bonded to the halogen become the two carbons with the double bond in the product alkene :0: CH3 Com The real value of the Wittig reaction lies in its ability to yield an alkene of predictable structure, as the C-C bond is precisely where the C=O bond was in the reactant and no isomers (other than…arrow_forwardDescribe the reaction mechanism for the hydrolysis of 2-bromo-2-methylpropane [CH3C(CH3)2Br] with aqueous hydroxide ions (OH-).arrow_forwardMyo-inositol, the most prominent naturally occurring form of inositols, is a carbocyclic polyol that plays an important role as the structural basis for a number of secondary messengers in eukaryotic cells. It is generated in vivo from the aldol cyclization of glucose-6-phosphate to myo-inositol-1-phosphatearrow_forward
- Write the complete mechanism for the hydroxide ion catalyze reaction of cyclohexanone and 1-methylcyclohexanecarbaldehydearrow_forwardA graduate student was studying enzymatic reductions of cyclohexanones when she encountered some interesting chemistry. When she used an enzyme and NADPH to reduce the following ketone, she was surprised to find that the product was optically active. She carefully repurified the product so that no enzyme, NADPH, or other contaminants were present. Still, the product was optically active. If this reaction could be accomplished using H2 and a nickel catalyst, would the product be optically active? Explain.arrow_forwardOn acid-catalyzed dehydration, 1-butanol (CH3CH2CH2CH2OH) can be converted to 1-butene. Write out an equation for the reaction Assign each the appropriate symbol for the mechanism of the reaction (E1 or E2) Draw a suitable mechanism for the reactionarrow_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
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning