EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 23.2, Problem 5P
Instead of adding to the 4a position and protonating N-5, the thiolate ion could have added to the 10a position and protonated N-l. (The numbering system is on page 1071.) Why is addition to the 4a position favored? (Hint: Which nitrogen is a stronger base?)
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Chapter 23 Solutions
EBK ORGANIC CHEMISTRY
Ch. 23.1 - Prob. 2PCh. 23.1 - Prob. 3PCh. 23.2 - How many conjugated double bonds are there in a....Ch. 23.2 - Instead of adding to the 4a position and...Ch. 23.2 - Prob. 7PCh. 23.3 - Prob. 8PCh. 23.3 - Acetolactate synthase is another TPP-requiring...Ch. 23.3 - Acetolactate synthase transfers the acyl group of...Ch. 23.3 - Prob. 12PCh. 23.5 - Which compound is more easily decarboxylated?
Ch. 23.5 - Prob. 14PCh. 23.5 - Explain why the ability of PLP to catalyze an...Ch. 23.5 - Explain why the ability of PLP to catalyze an...Ch. 23.5 - The enzyme that catalyzes the C C bond cleavage...Ch. 23.5 - Propose a mechanism for the ,-elimination reaction...Ch. 23.6 - Ethanolamine ammonia lyase, a coenzyme...Ch. 23.6 - Prob. 20PCh. 23.7 - How do the structure of tetrahydrofolate and...Ch. 23.7 - What is the source of the methyl group in...Ch. 23.8 - Thiols such as ethanethiol and propanethiol can be...Ch. 23 - How does the metal ion in carboxypeptidase A...Ch. 23 - Prob. 24PCh. 23 - Prob. 25PCh. 23 - For each of the following reactions, name both the...Ch. 23 - Prob. 27PCh. 23 - When transaminated, the three branched-chain amino...Ch. 23 - What acyl groups have we seen transferred by...Ch. 23 - Propose a mechanism for the following reaction:Ch. 23 - Draw the products of the following reaction, where...Ch. 23 - When UMP is dissolved in T2O, exchange of T for H...Ch. 23 - Dehydratase is a PLP-requiring enzyme that...Ch. 23 - In addition to the reaction mentioned in Section...Ch. 23 - PLP can catalyze both ,-elimination reactions...Ch. 23 - The glycine cleavage system is a group of four...Ch. 23 - Prob. 37PCh. 23 - FADH2 reduces , -unsaturated thioesters to...
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- ONANO (a) Circle the two compounds that are not carboxylic acid derivatives. Circle only two. CONHCH3 CN =NOH NH COCI (b) Circle the two compounds that can be hydrolyzed to a ketone in aqueous acid. Circle only two. N-PH (c) Circle the two compounds that can be converted to an aldehyde by reduction using DIBAL (also known as DIBAL-H). Circle only two. .CHO он CN (d) Circle the two most reactive compounds with water. Circle only two DEt OMe NH2 CH;CH,CN (e) Circle the strongest acid. [2 marks] CO.Et CO-H NO2 CHO (1) Circle ethyl benzoate and maleic anhydride. COCH,CH, .Co.CH,CH3 (g) Circle the two compounds that can be reduced to an amine using NaBH4. Circle only two. 'NH2 CN NHarrow_forwardThe product in this reaction is basic enough to be protonated by a dilute HCl solution. Draw the protonated species, clearly showing where protonation occurs. Draw all possible resonance structures of the conjugate acid of the product, and use these to explain why the product is so much more basic than a typical ester, like ethyl acetate.arrow_forwardDraw the structure of the conjugate base of the acid given below. (Note that the acidic H in consideration is bold and underlined.)arrow_forward
- Help me pleasearrow_forward51. Which is NOT a valid resonance structure for the conjugate base of this molecule? (A) (C) S (A) OEt O :O: : OEt HBr ROOR OCH 3 (B) 52. What is the major product of this reaction sequence? O PPh3 (D) 11 Mg ether (B) de OEt :0 aom Сосно LOCH 3 53. Which reagent is necessary for this transformation? (D) H OEt H OEt CH31 PPh3 ACS 56.arrow_forwardDraw the major organic product of the Bronsted acid-base reaction between the compounds shown below. Include all lone pairs and charges as appropriate. Ignore any counterions. HH 1 eq. base Drawing H H 'Н Qarrow_forward
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