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5. Ribose's structure is OH HO ОН ОН OH OH a) Draw using the arrow formalism the reaction of linear ribose to make a 5-membered ring. b) What is the name of the resulting functional group? c) Given that reaction of alcohols (such as RCH2OH) with carbonyls (such as HCO-R') to create this functional group is typically not thermodynamically favored, why does most ribose in water exist as a 5-membered ring? A few word answer is fine. d) AGfor thir roction ic about 5 k/mol Assuming that vou start with mM colution of

5. Ribose's structure is OH HO ОН ОН OH OH a) Draw using the arrow formalism the reaction of linear ribose to make a 5-membered ring. b) What is the name of the resulting functional group? c) Given that reaction of alcohols (such as RCH2OH) with carbonyls (such as HCO-R') to create this functional group is typically not thermodynamically favored, why does most ribose in water exist as a 5-membered ring? A few word answer is fine. d) AGfor thir roction ic about 5 k/mol Assuming that vou start with mM colution of

Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
ChapterNW1: Nomenclature Worksheet 1: Naming Alkanes & Cycloalkanes
Section: Chapter Questions
Problem 18CTQ
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5. Ribose's structure is ОН HO ОН ОН a) Draw using the arrow formalism the reaction of linear ribose to make a 5-membered ring. b) What is the name of the resulting functional group? c) Given that reaction of alcohols (such as RCH2OH) with carbonyls (such as HCO-R') to create this functional group is typically not thermodynamically favored, why does most ribose in water exist as a 5-membered ring? A few word answer is fine. d) AG°for this reaction is about - 5 kJ/mol. Assuming that you start with a 1 mM solution of ribose in water, what is the approximate concentration at equilibrium of (i) the linear form? (ii) The cyclic form? (A good answer should be correct within 20%, e.g. it is fine to approximate 9 mM as 10 mM, but it is not okay to approximate 0.1 mM as 1 mM.) e) This reaction creates a new stereocenter. Please indicate it with a *. f) Consider the starting point for synthesis of purines like ATP, which is PRPP (pheseboribosylevOrhesehate) НО НО LOLOH HO ОН HO OH Pyrophosphate (on the right-hand side of the molecule) is a good leaving group. Draw the leaving of pyrophosphate (the whole thing, so no phosphate is left at this position) using the arrow formalism, and the resulting organic (i.e. carbon-containing) product, including any formal charge. g) Draw a resonance form that stabilizes this product. h) In purine synthesis, this product reacts with ammonia. Draw the reaction mechanism using the arrow formalism and the resulting new compound.
Transcribed Image Text:5. Ribose's structure is ОН HO ОН ОН a) Draw using the arrow formalism the reaction of linear ribose to make a 5-membered ring. b) What is the name of the resulting functional group? c) Given that reaction of alcohols (such as RCH2OH) with carbonyls (such as HCO-R') to create this functional group is typically not thermodynamically favored, why does most ribose in water exist as a 5-membered ring? A few word answer is fine. d) AG°for this reaction is about - 5 kJ/mol. Assuming that you start with a 1 mM solution of ribose in water, what is the approximate concentration at equilibrium of (i) the linear form? (ii) The cyclic form? (A good answer should be correct within 20%, e.g. it is fine to approximate 9 mM as 10 mM, but it is not okay to approximate 0.1 mM as 1 mM.) e) This reaction creates a new stereocenter. Please indicate it with a *. f) Consider the starting point for synthesis of purines like ATP, which is PRPP (pheseboribosylevOrhesehate) НО НО LOLOH HO ОН HO OH Pyrophosphate (on the right-hand side of the molecule) is a good leaving group. Draw the leaving of pyrophosphate (the whole thing, so no phosphate is left at this position) using the arrow formalism, and the resulting organic (i.e. carbon-containing) product, including any formal charge. g) Draw a resonance form that stabilizes this product. h) In purine synthesis, this product reacts with ammonia. Draw the reaction mechanism using the arrow formalism and the resulting new compound.
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