7. Acetone reacts with carbohydrates in the presence of an acid catalyst to form products that are commonly referred to as "isopropylidene" or "acetonide" derivatives. The carbohydrate D-ribono-(1,4)-lactone reacts with acetone in the presence of hydrochloric acid to give the acetonide shown here. Utilizing chemistry knowledge from chapter 18,write a mechanism for this reaction (Hint: What kind of compound has been made?). HO HO OH OH HCI + H₂0

7. Acetone reacts with carbohydrates in the presence of an acid catalyst to form products that are commonly referred to as "isopropylidene" or "acetonide" derivatives. The carbohydrate D-ribono-(1,4)-lactone reacts with acetone in the presence of hydrochloric acid to give the acetonide shown here. Utilizing chemistry knowledge from chapter 18,write a mechanism for this reaction (Hint: What kind of compound has been made?). HO HO OH OH HCI + H₂0

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter9: Nucleophilic Substitution And Β-elimination

Section: Chapter Questions

Problem 9.62P

See similar textbooks

Similar questions

A ketone undergoes acid-catalyzed bromination, acid-catalyzed chlorination, racemization, (see page 408)and acid-catalyzed deuterium exchange at the a-carbon. All of these reactions have similar rate constants.What does this tell you about the mechanisms of these reactions?
A ketone undergoes acid-catalyzed bromination, acid-catalyzed chlorination, racemization, and acid-catalyzed deuterium exchange at the alpha-carbon. All of these reactions have similar rate constants. What does this tell you about the mechanisms of these reactions?
Enamines can serve as enolate surrogates in reactions at the α-carbon. In the reaction sequence, the structures of the enamine addition product - the initial zwitterion and its neutral tautomer - are shown. Draw the structures of the two reactants forming these intermediates, and draw the structure of the final product, obtained via hydrolysis of the neutral intermediate. initial zwitterionic intermediate 'N + 85 Reactants tautomerization hydrolysis product neutral intermediate 80 + H₂O
Enamines can serve as enolate surrogates in reactions at the a-carbon. In the reaction sequence, the structures of the enamine addition product – the initial zwitterion and its neutral tautomer – are shown. Draw the structures of the two reactants forming these intermediates, and draw the structure of the final product, obtained via hydrolysis of the neutral intermediate. initial zwitterionic intermediate neutral intermediate tautomerization Reactants H20 hydrolysis product Draw the two reactants. Draw the hydrolysis product.
Identify A, B, and C, intermediates in the synthesis of the ve-membered ring called an α-methylene-γ-butyrolactone. This heterocyclic ring system is present in some antitumor agents.
2) a) n-Butyllithium is used to deprotonate the following compounds. Draw the structures of the resulting organolithium compounds (assume they are monomeric). Me₂N SO₂ b) Explain the selectivity of deprotonation. c) Each organolithium is reacted with ethyltosylate. Draw the structures of the resulting products.
When compound (A) is treated with Cl-, the result is (B), as shown at the right. You might want to number your carbons. Just sayin'. RO When 2-(2-hydroxyhept-6-en-2-yl)phenol (C) is treated with aqueous acid, the result is 6,7-benzo-1,5-dimethyl-8-oxabicyclo[4.3.1]nonane (D), as shown at the right. You might want to number your carbons. Just sayin'. -N (A) Give a detailed, stepwise mechanism that accounts for the formation of (B) from (A). OTf Give a detailed, stepwise mechanism that accounts for the formation of (D) from (C). CH,Ph OH OH (C) CI RO H3O* N. (B) CH₂CI CH,Ph (D) + OTf
Complete the synthesis of (R)-4-methyl-2-((R)-1-(phenylthio)ethyl)pentane-1,2-diol from the starting material given ((Z)-2-isopropylbut-2-enal). You must list out all reagents/solvents used and draw the intermediate structures. You do NOT have to draw the mechanisms. Hint: the stereochemistry is very important. OH -OH
Non-conjugated β,γ-unsaturated ketones, such as 3-cyclohexenone, as in acid-catalysed equilibrium with their α,β-unsaturated isomers. The mechanism has several intermediates. Draw the structure of the second reaction intermediate in the conversion of 3-cyclohexenone to 2-cyclohexenone. This intermediate is a neutral compound.
When the compound shown below undergoes acid-catalyzed dehydration, a ring expansionoccurs to give the fused-ring product. What type of intermediate is formed in this reaction?Explain the ring expansion in terms of the reaction mechanism
Provide the mechanism for this reaction (include arrow pushing) ОН 2-lodobenzoic acid K2S2O8 H2SO4 ОН OSO3H ОН 양 diphenyliodonium-2-Carboxylate benzyne
The ketone shown was prepared in a three-step sequence from ethyl trifluoroacetate. The first step in the sequence involved treating ethyl trifluoroacetate with ammonia to give compound A. Compound A was in turn converted to the desired ketone by way of compound B. Fill in the missing reagents in the sequence shown, and give the structures of compounds A and B.