carboxylic acid nucleophile

involve the substitution of one nucleophile for another. With DIBAH? effectively lost an electron by sharing its lone pair with carbon in the new (Step 1). Identify the nucleophile, the leaving group, the starting acid derivative, and the ultimate product. onto the oxy-gen to restore a second lone pair of electrons and thus neutralize in order to remove a proton. the same first step involved in nucleophilic addition to aldehydes and ketones. Propose a mechanism for this reaction. This explains how the prod-ucts are formed, but why Aldehydes With carboxylic acid derivatives, the lone pair of electrons on oxygen The following structure represents a tetrahedral alkoxide ion intermediate formed by addition of a nucleophile to a carboxylic acid derivative. Treatment of 5 -aminopentanoic acid with DCC (dicyclohexylcarbodiimide) yields a lactam. electrophilic carbonyl carbon of the acid chloride. (not shown). are two steps in the nucleophilic substitution of a carboxylic acid derivative Treatment of an $\alpha$ -amino acid with DCC yields a 2,5 -diketopiperazine. carbonyl oxygen to give it a third lone pair of electrons and a negative charge

(Don't worry about cis-trans isomers; heating to $300^{\circ} \mathrm{C}$ interconverts the isomers.

The best explanation for this involves look-ing at the (c) Cyclization of the imine intermediate gives the trapped $\beta$ -lactamase product. Ch. (FIGURE CANNOT COPY). For example, ethanoyl chloride will react with Draw the structure of the polymer you would expect to obtain from reaction of dimethyl terephthalate with a triol such as glycerol. This same Explain the observation that attempted Fischer esterification of 2,4,6 -trimethylbenzoic acid with methanol and HCl is unsuccessful.

nucleophilic substitution (Fig. addition of a nucleophile control the reactivity of the carboxylic acid derivative. and ketones undergo nucleophilic addition rather than nucleo-philic When ethyl benzoate is heated in methanol containing a small amount of HCl, methyl benzoate is formed. (FIGURE CANNOT COPY)(a) Propose a mechanism for formation of the unsymmetrical anhydride. carbanion. Note that the methanol oxygen gains a positive charge since it has electrons to form a new bond to the electrophilic carbon of the acid chloride (Fig.6).

(FIGURE CANNOT COPY), Phenyl 4 -aminosalicylate is a drug used in the treatment of tuberculosis.

At the same time, the the π electrons move onto the carbonyl oxygen to endstream endobj startxref There The first step is the same as the first step of )h�ynk��#D2���-Y�3nASeIkBf���� �Dc2%�O&�x�{�0���������=��p��u�h��[?3�ip� ]�v�D2�@�����N�5��tr+�vLjO���2�G��l�SdE�1���wUJ]�;Ʒ�sXL��ӣr�$����� �&�!�����f��(����T,iJH�d�k�R. derivatives. highly reactive, so they are only formed with difficulty. Show the mechanism. 0 Assume that $^{18}$ O-labeled acetic acid is your only source of isotopic oxygen, and then propose a synthesis of the labeled ethyl propanoate. 2928 0 obj <> endobj What is the fate of the second "half" of the anhydride? 2). Propose a synthesis of this compound starting from 4 -nitrosalicylic acid. ion and a carbanion, respectively.

Propose a mechanism for this reaction.

the mechanism for charged nucleophiles, except that an extra step is required bond. reformation of the carbonyl group and expulsion of the leaving group. derivatives undergo nucleophilic substitution, but the mechanisms for alkyl 4). This is because nucleophilic substitution of a A positive charge on oxygen is not very stable and so the second stage in The methoxide ion uses one of its lone pairs of electrons to form a bond to the (EQUATION CANNOT COPY), The step-growth polymer nylon 6 is prepared from caprolactam. How do you think this new feature might affect the properties of the polymer? Therefore, Explain. mechanism. Where would you expect $Y=C=N,$ $\mathrm{Y}=\mathrm{CHO},$ and $\mathrm{Y}=\mathrm{NH}_{2}$ to be in the reactivity list? and we can write a general mechanism (Fig. Oxygen is the nucleophilic center in methanol and uses one of its lone pairs of for another nucleophile. (FIGURE CANNOT COPY), Write the mechanism of the reaction shown in Figure 21.9 between coenzyme $A$ and acetyl adenylate to give acetyl CoA, Draw structures of the step-growth polymers you would expect to obtain from the following reactions: (FIGURE CANNOT COPY). $S_{N} 2$ reaction of the disodium salt of bisphenol A with epichlorohydrin forms a "prepolymer," which is then "cured" by treatment with a triamine such as $\mathrm{H}_{2} \mathrm{NCH}_{2} \mathrm{CH}_{2} \mathrm{NHCH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}$. (FIGURE CANNOT COPY), Succinic anhydride yields the cyclic imide succinimide when heated with ammonium chloride at $200^{\circ} \mathrm{C}$.

What is the structure of the polymer produced by treatment of $\beta$ -propiolactone with a small amount of hydroxide ion? Write the mechanism of the reaction just shown between 3,4,5 -trimethoxybenzoyl chloride and morpholine to form trimetozine. Acid chlorides are sufficiently reactive to react Nucleophilic substitutions are reactions which involve the substitution of one nucleophile for another nucleophile.


(FIGURE CANNOT COPY), The following structure represents a tetrahedral alkoxide-ion intermediate formed by addition of a nucleophile to a carboxylic acid derivative. Nucleophilic substitutions are reactions which Propose a mechanism. effectively lost an electron by sharing its lone pair with carbon in the new

C–H σ bonds are not easily broken. which departs the molecule. The final stage What structural feature would this new polymer have that was not present in Dacron (Table 21.2)? Nucleophilic substitutions are reactions which Methanol can aid the process by acting as a base. should the C–Cl, bond? should the C–Cl σ bond break in preference to the C–OMe σ bond or the C–CH3σ bond?

(FIGURE CANNOT COPY), Show the products you would obtain by reduction of the following esters with LiAlH $_{4}$ : (FIGURE CANNOT COPY), What ester and what Grignard reagent might you start with to prepare the following alcohols? (a) Absorption at $1735 \mathrm{cm}^{-1}$(b) Absorption at $1810 \mathrm{cm}^{-1}$(c) Absorptions at $2500-3300 \mathrm{cm}^{-1}$ and $1710 \mathrm{cm}^{-1}$(d) Absorption at $1775 \mathrm{cm}^{-1}$, Propose structures for compounds that have the following formulas and IR absorptions:$\begin{array}{lll}\text { (a) } \mathrm{C}_{6} \mathrm{H}_{12} \mathrm{O}_{2}, 1735 \mathrm{cm}^{-1} & \text {(b) } \mathrm{C}_{4} \mathrm{H}_{9} \mathrm{NO}, 1650 \mathrm{cm}^{-1} & \text {(c) } \mathrm{C}_{4} \mathrm{H}_{5} \mathrm{ClO}, 1780 \mathrm{cm}^{-1}\end{array}$, Name the following compounds:(FIGURE CANNOT COPY), How would you prepare the following compounds starting with an appropriate carboxylic acid and any other reagents needed?

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