Concept explainers
(a)
Interpretation:
The change in the product ratios with an increase in temperature is to be explained.
Concept introduction:
Sulfonation of benzene derivatives is done to synthesise arylsulfonic acids. It is an electrophilic
(b)
Interpretation:
The consequence of heating product mixture from reaction at
Concept introduction:
Sulfonation of benzene derivatives is done to synthesise arylsulfonic acids. It is an electrophilic aromatic substitution. In such type of reactions, sulfur trioxide acts as the electrophile. A solution of
(c)
Interpretation:
The method of synthesis of
Concept introduction:
Sulfonation of benzene derivatives is done to synthesise arylsulfonic acids. It is an electrophilic aromatic substitution. In such type of reactions, sulfur trioxide acts as the electrophile. A solution of
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Organic Chemistry (9th Edition)
- Alcohols 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_forwardNonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardAn important step in one synthesis of carboxylic acids is the deprotonation of diethyl malonate and its alkyl-substituted derivative: Base CH;CH2O OCH,CH3 CH;CH,0 OCH2CH3 H2 Diethyl malonate Base CH;CH,0 °C `OCH,CH3 CH;CH,O OCH,CH3 R Alkyl substituted diethyl malonate NaOH can deprotonate diethyl malonate effectively, but NaOC(CH3)3 is typically used to deprotonate the alkyl-substituted derivative. Explain why.arrow_forward
- Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions -X티 Hö: H-O -CH3 -CH3 H30*arrow_forwardThe reaction of methylpropene with HBr, under radical conditions, gives two intermediates. Propose a mechanism for the formation of the two products. Propose a mechanism for the following reaction and use electronic factors to account for the formation of a major product: CH2 CH2Br N-Bromosuccinimide (NBS) ho, CCI4 Draw the structure of an antioxidant, Vitamin E free radical and use resonance structures o account for its stability.arrow_forwardChoose 2 of the 3 compounds and provide a synthesis starting with benzene and any other carbon compound with four or less carbons.arrow_forward
- Alkylation of benzene with 1-chlorobutane in the presence of AlCl3 gave not only the expected butylbenzene product but also, as a major product, (1-methylpropyl)benzene. Write an equation for the reaction Propose a mechanism to account for the formation of butylbenzene Propose a mechanism to account for the formation of (1-methylpropyl)benzenearrow_forwardA synthon is a concept in retrosynthetic analysis. It is defined as a structural unit within a molecule which is related to a possible synthetic operation. Example: OH bond breaks here synthesis Br + retrosynthesis NEC Na -NaBr Synthons C-C bond formation synthetic equivalents Br D=00 CN OH || ⒸC=N H₂O, H+ hydrolysis do not exist exist functional group transformation Common synthons: C1 synthons: carbon dioxide, carbon monoxide, cyanide, formaldehyde C2 synthons: acetylene, acetaldehyde C₂H4OH synthon: ethylene oxide OH Carbocation synthons: alkyl halides, carbonyl C Carbanion synthons: Grignard reagents, organolithiums, malonic ester/acetoacetic ester, terminal alkyne Use the synthons listed above, propose how you would synthesis the following molecules:arrow_forwardAlcohols are acidic in nature. Therefore, a strong base can abstract the acidic hydrogen atom of the alcohol in a process known as deprotonation. The alcohol forms an alkoxide ion by losing the proton attached to the oxygen atom of the hydroxyl ( -OH) group. The alkoxide formed can act as a base or a nucleophile depending on the substrate and reaction conditions. However, not all bases can abstract the acidic proton of alcohols and not all alcohols easily lose the proton. Deprotonation depends on the strength of the base and the acidity of the alcohol. Strong bases, such as NaNH2, can easily abstract a proton from almost all alcohols. Likewise, more acidic alcohols lose a proton more easily. Determine which of the following reactions would undergo deprotonation based on the strength of the base and the acidity of the alcohol. Check all that apply. ► View Available Hint(s) CH3CH,OH + NH3 →CH,CH,O-NH CH3 CH3 H3C-C-H+NH3 → H3 C-C-H OH O-NH CH3CH2OH + NaNH, → CH3CH,O-Na* + NH3 CHC12 Cl₂…arrow_forward
- From the table of available reagents select the one(s) you would use to convert:3-pentanol to 3-bromopentane:cyclopentanol to trans-2-methylcyclopentanol:Use the minimum number of steps; in no case are more than four steps necessary.List reagents by letter in the order that they are used; example: fa.arrow_forwardWhat type of substituent effect do you expect a -CC12-CC12-CC13 (perchloropropyl) group to have upon aromatic electrophilic substitution reactions? Resonance electron donor; activating substituent; ortho/para director Inductive electron donating; activating substituent; ortho/para director Resonance electron withdrawing; deactivating substituent; ortho/para director Inductive electron withdrawing; deactivating substituent; meta directorarrow_forwardThis reaction does not take place. All that happens under experimental conditions for the formation of radicals is initiation to form iodine radicals, I·, followed by termination to reform I2. How do you account for these observations?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningIntroduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning