Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 15.8, Problem 24P
Show the mechanism for the acid-catalyzed formation of 23c starting with the product from its hydrolysis.
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Start with the condensed structural formula CH2=CH-CH2-CH(CH3)2, and react it first with H2O in the presence of H2SO4 (as the catalyst), to produce a major substrate product. Then, take that major substrate product, and use it as the substrate of the next reaction, by reacting it with K2Cr2O7 and H2SO4, to produce the FINAL MAJOR substrate product.
The complete correct condensed structural formula for the major substrate product (after reaction step 1) is .
The complete correct condensed structural formula for the final major substrate product (after reaction step 2) is .
Start with the condensed structural formula
CH2=CH-CH2-CH2-CH(CH3)2
and react it first with H2O in the presence of H2SO4 (as the catalyst), to produce a major substrate product. Then, take that major substrate product, and use it as the substrate of the next reaction, by reacting it with K2Cr2O7 and H2SO4, to produce the FINAL MAJOR substrate product.
The complete correct condensed structural formula for the major substrate product (after reaction step 1) is __________. (If no new product is formed in this step, type "no reaction.")
The complete correct condensed structural formula for the final major substrate product (after reaction step 2) is __________. (If no new product is formed in this step, type "no reaction.")
What is the product of the starting material D-glyceraldehyde which will
(1) produce aldaric acid upon reacting with HNO3 + H2O, NaOCH2, NH2OH, and (CH3CO)2O + NaOCOCH3
(2) produce tartaric acid upon reacting with HNO3 + H2O, NaOCH3, NH2OH, and (CH3CO)2O + NaOCOCH3
Chapter 15 Solutions
Organic Chemistry (8th Edition)
Ch. 15.1 - The aromas of many flowers and fruits are due to...Ch. 15.1 - Name the following:Ch. 15.1 - Prob. 3PCh. 15.2 - Which is longer, the carbon-oxygen single bond in...Ch. 15.2 - There are three carbon-oxygen bonds in methyl...Ch. 15.2 - Prob. 6PCh. 15.4 - a. What is the product of the reaction of acetyl...Ch. 15.4 - What is the product of an acyl substitution...Ch. 15.5 - a. Which compound has the stretching vibration for...Ch. 15.5 - Using the pKa values listed in Table 15.1, predict...
Ch. 15.5 - Is the following statement true or false? If the...Ch. 15.6 - Starting with acetyl chloride, what neutral...Ch. 15.6 - Prob. 13PCh. 15.7 - Starting with methyl acetate, what neutral...Ch. 15.7 - We saw that it is necessary to use excess amine in...Ch. 15.7 - Prob. 17PCh. 15.7 - Which ester hydrolyzes more rapidly? a. methyl...Ch. 15.7 - a. state three factors that cause the uncatalyzed...Ch. 15.8 - Prob. 21PCh. 15.8 - Using the mechanism for the acid-catalyzed...Ch. 15.8 - Prob. 23PCh. 15.8 - Show the mechanism for the acid-catalyzed...Ch. 15.8 - Prob. 25PCh. 15.8 - Write the mechanism for the acid-catalyzed...Ch. 15.8 - Write the mechanism for the acid-catalyzed...Ch. 15.9 - Prob. 28PCh. 15.9 - Prob. 29PCh. 15.10 - Show how each of the following esters could he...Ch. 15.10 - Prob. 32PCh. 15.11 - Prob. 33PCh. 15.11 - Which of the following reactions leads to the...Ch. 15.12 - Prob. 35PCh. 15.12 - Prob. 36PCh. 15.13 - Prob. 37PCh. 15.14 - Prob. 38PCh. 15.14 - Prob. 39PCh. 15.15 - Prob. 40PCh. 15.15 - Which alkyl halides from the carboxylic acids...Ch. 15.16 - Prob. 43PCh. 15.16 - Prob. 44PCh. 15.16 - Prob. 45PCh. 15.17 - Prob. 46PCh. 15.18 - How could you synthesize the following compounds...Ch. 15 - Prob. 48PCh. 15 - Name the following:Ch. 15 - Prob. 50PCh. 15 - What compound are obtained from the fallowing...Ch. 15 - a. Rank the following esters in order of...Ch. 15 - Because bromocyclohexane is a secondary alkyl...Ch. 15 - a. Which compound would you expect to have a...Ch. 15 - How could you use 1H NMR spectroscopy to...Ch. 15 - Rank the following compounds in order of...Ch. 15 - Prob. 57PCh. 15 - Prob. 58PCh. 15 - Prob. 59PCh. 15 - A compound with molecular formula C5H10O2 gives...Ch. 15 - Prob. 61PCh. 15 - Prob. 62PCh. 15 - Prob. 63PCh. 15 - Prob. 64PCh. 15 - Prob. 65PCh. 15 - Prob. 66PCh. 15 - Two products, A and B, are obtained from the...Ch. 15 - Prob. 68PCh. 15 - Prob. 69PCh. 15 - Prob. 70PCh. 15 - Prob. 71PCh. 15 - Prob. 72PCh. 15 - When treated with an equivalent of methanol,...Ch. 15 - a. Identify the two products obtained from the...Ch. 15 - Prob. 75PCh. 15 - Prob. 76PCh. 15 - a. When a carboxylic acid is dissolved in...Ch. 15 - Prob. 78PCh. 15 - Identity the major and minor products of the...Ch. 15 - When a compound with molecular formula C11H14O2...Ch. 15 - Prob. 81PCh. 15 - Prob. 82PCh. 15 - Prob. 83PCh. 15 - The 1H NMR spectra for two esters with molecular...Ch. 15 - Show how the following compounds could be prepared...Ch. 15 - Prob. 86PCh. 15 - Prob. 87PCh. 15 - The intermediate shown here is formed during the...Ch. 15 - Prob. 89PCh. 15 - Propose a mechanism that accounts for the...Ch. 15 - Catalytic antibodies catalyze a reaction by...Ch. 15 - Prob. 92P
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- When HOCH2CH2CH2CH2COCH2CH2CH2CH2OH is heated in the presence of an acid catalyst, a reaction occurs. This product has the formula C9H16)2. Provide the structure of this product.arrow_forwardGiven the reaction of the synthesis of ethyl acetate: CH3COCH3 + Br2 + H3O+ → CH3COCH2Br + HBr + H3O+ Which is the catalyst? H3O+ CH3COCH3 CH3COCH2Br Br2arrow_forwardGive the reactant or the product of the followingarrow_forward
- Complete the following reaction by drawing a structural formula for the product. CH₂CH3 + H₂ Ni or Pt ?arrow_forwardAldehydes and ketones that have a hydrogen atom at the alpha position can be converted into a carbanion in the presence of a base as follows. This source of the stability of this carbanion is -H2 gas + polar interaction between the negative charge and the partial positive charges in the solvent O delocalization of the negative charge to the adjacent carbonyl group the electron donating effect of the alpha carbon the electron withdrawing effect of the alpha carbonarrow_forwardComplete the following equation to show the product obtained from the reaction.arrow_forward
- Which of the following chemical equations depicts an alkylation reaction? C6H6() + CH3Cl() → C6H5CH3() + HCl(g) 2 CH3OH() + 3 O2(g) → 2 CO2(g) + 4 H2O() C6H12() → C6H10() + H2(g) CH2ClCH2Cl(g) + H2(g) → CH3CH3(g) + Cl2(g) CHClCHCl(g) → CH2ClCH2Cl(g)arrow_forwardQ2: Write the structure of the product formed in each case (A) C6H₂CH₂CH₂C6H₁ H₂C=CHCCH₂ NaOCH, CH₂OHarrow_forwardSYNTHESIS OF ESTERS VIA NUCLEOPHILIC ACYL SUBSTITUTION Write the chemical equation involved in the reaction between the excess acid and NaHCO3. Explain why NaHCO3 is preferred over NaOH for the neutralization of excess acid. How was excess alcohol eliminated from the crude product.arrow_forward
- Write the product(s) for the following reaction.arrow_forwardThe oxidation of an aldehyde is commonly carried out using potassium permanganate or potassium dichromate. In fact, the carbon alpha to a benzene ring is very reactive, hence it is possible to oxidize an alkyl benzene compound at the alpha position. Give the equation for the reaction of toluene to benzoic acid using potassium permanganate.arrow_forwardWhy does the addition of bromine to fumaric acid require a high temperature for the reaction while other substrates (generic alkanes, alkenes, and alkynes) react with bromine at room temperature?arrow_forward
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