Concept explainers
(a)
To determine: The reason corresponding to the fact that an NHS ester is much more reactive than a simple alkyl ester.
Interpretation: The reason corresponding to the fact that an NHS ester is much more reactive than a simple alkyl ester is to be stated.
Concept introduction: The compound containing a good leaving group that has molecular formula
(b)
To determine: The mechanism for the given reaction that coverts an acid to NHS ester.
Interpretation: The mechanism for the given reaction that coverts an acid to NHS ester is to be predicted.
Concept introduction: The compound containing a good leaving group that has molecular formula
(c)
To determine: The mechanism for the reaction of NHS ester with an
Interpretation: The mechanism for the reaction of NHS ester with an amine,
Concept introduction: The compound containing a good leaving group that has molecular formula
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Organic Chemistry (9th Edition)
- a. Compound X is benzene, Y is acetic anhydride acid. Complete the following scheme and determine Z! b. Determine which reagents except acetic acid anhydrides can replace Y!arrow_forwarda. What carboxylic acid is formed when the malonic ester synthesis is carried out with one equivalent of malonic ester, one equivalent of 1,5-dibromopentane, and two equivalents of base?b. What carboxylic acid is formed when the malonic ester synthesis is carried out with two equivalents of malonic ester, one equivalent of1,5-dibromopentane, and two equivalents of base?arrow_forwardQ6 Complete the retrosynthetic analysis. Supply all reagents and precursors, for both parts: A and B. Fewest possible reaction paths should be choiun. Part A V Part B Miarrow_forward
- Which substrate will you use to synthesize 1-propanol from propanal? A.) NaBH₄ B.) O₃ C.) KMnO₄ D.) CH₃MgCl E.) None of the given answerarrow_forward1. Br₂, PBrg 2. H₂O H₂C OH H3C OH Br The a-bromination of carbonyl compounds by Br₂ in acetic acid is limited to aldehydes and ketones because acids, esters, and amides don't enolize to a sufficient extent. Carboxylic acids, however, can be a-brominated by first converting the carboxylic acid to an acid bromide by treatment with PBr3. Following enolization of the acid bromide, Br₂ reacts in an α- substitution reaction. Hydrolysis of the acid bromide completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H3C :0: :0::Br: Br Br H3C CO-P H Br Brarrow_forward1. Predict the major product(s) obtained when the following compounds undergo hydrolysis in the presence of H3O+. Explain how you would reverse each reaction. a. b.arrow_forward
- a. When a carboxylic acid is dissolved in isotopically labeled water (H218O) and an acid catalyst is added, the label is incorporated into both oxygens of the acid. Propose a mechanism to account for this. b. If a carboxylic acid is dissolved in isotopically labeled methanol (CH318OH) and an acid catalyst is added, where will the label reside in the product?c. If an ester is dissolved in isotopically labeled water (H218O) and an acid catalyst is added, where will the label reside in the product?arrow_forwardAcid anhydrides are generally formed by strongly heating an acid solution which promotes dehydration. Intramolecular acid dehydrations create cyclic acid anhydrides. i. Besides providing energy for the reaction, how else does heating the acid solution promote the formation of the anhydride? ii. Write a mechanism for the dehydration of the following molecule (Hint: remember that cyclohexyl rings can flip) H CO Harrow_forward3. Show the mechanism for the following addition/substitution. cat. H2SO4 MeNH2 remove H₂O H H Why doesn't a primary amine need to add a second nucleophile? (i.e. why does it make an imine instead of an aminal?)arrow_forward
- 2. Propose a synthesis of the following molecule using an aldol reaction. OH 3. Imines can undergo reduction reactions with sodium borohydride to produce amines by a similar mechanism to how aldehydes and ketones react to produce alcohols. With thatin mind, propose a mechanism for the following reaction and give the structure of theamine product. N 1. NABH4 2. H30* iminearrow_forward23. What effect makes the chloride a good leaving group in acyl chloride? +1 -11 +M -M 24. What reagent would you treat an amine to convert it to: (i) an imine; and, (ii) amide? ketone; acyl chloride aldehyde; acyl chloride ketone; carboxylic acid O aldehyde; carboxylic acidarrow_forwardNH2 HO, H. Atenolol Tenormin® Below is a two-step reaction sequence. What are the steps in the synthesis? `NH2 -NH2 `NH2 base OH OH O The phenolate reacts with the epoxide preferentially over the alkyl halide at the less sterically hindered position. Then, the sterically hindered amine attacks the alkyl chloride. O The phenolate reacts with the epoxide preferentially over the alkyl halide at the more sterically hindered position. Then, the sterically hindered amine attacks the alkyl chloride.arrow_forward