One frequently used method for preparing methyl esters is

Give IUPAC names for the following substances: Equation Transcription: Text Transcription: CH_3 CH_3CHCH_2CH_2CCl CH_2CNH_2 CH_3CHCOCHCH_3 OCHCH_3 CH_3 CH_3 CHCH_3 H_2C=CHCH_2CH_2CNHCH_3 H_3C OPO_32- H_3C H_3C CH_3 C-SCH_2CH_3

Draw structures corresponding to the following names: (a) Phenyl benzoate (b) N-Ethyl-N-methylbutanamide (c) 2,4-Dimethylpentanoyl chloride (d) Methyl 1-methylcyclohexanecarboxylate (e) Ethyl 3-oxopentanoate (f) Methyl p-bromobenzenethioate (g) Formic propanoic anhydride (h) cis-2-Methylcyclopentanecarbonyl bromide

Show the mechanism of the following nucleophilic acyl substitution reaction, using curved arrows to indicate the electron flow in each step: Equation Transcription: Text Transcription: Cl Na+ -OCH_3 CH_3OH OCH_3

Predict the product of the following nucleophilic acyl substitution reaction of benzoyl chloride with 2-propanol: Equation Transcription: Text Transcription: Cl OH CH3CHCH3

Rank the compounds in each of the following sets in order of their expected reactivity toward nucleophilic acyl substitution: Equation Transcription: Text Transcription: CH_3CCl, CH_3COCH_3, CH_3CNH_2 CH_3COCH_2CH_3, CH_3COCH_2CCl_3, CH_3COCH(CF_3)_2

Predict the products of the following nucleophilic acyl substitution reactions: Equation Transcription: Text Transcription: H_3C OCH_3 NaOH H_2O H_3C Cl NH_3 H_3C CH_3 Na+ -OCH_3 CH_3OH H_3C SCH_3 CH_3NH_2

The following structure represents a tetrahedral alkoxide ion intermediate formed by addition of a nucleophile to a carboxylic acid derivative. Identify the nucleophile, the leaving group, the starting acid derivative, and the ultimate product.

How might you prepare the following esters from the corresponding acids? Equation Transcription: Text Transcription: H_3C CH_2CH_2CH_2CH_3 CH_3CH_2CH_2 CH_3 CH_3 CH_3

If the following molecule is treated with acid catalyst, an intramolecular esterification reaction occurs. What is the structure of the product? (Intramolecular means within the same molecule.)

How might you prepare the following esters using a nucleophilic acyl substitution reaction of an acid chloride? (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{CH}_{3}\) (b) \(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) (c) Ethyl benzoate Equation Transcription: Text Transcription: CH_3CH_2CO_2CH_3 CH_3CO_2CH_2CH_3

Which method would you choose if you wanted to prepare cyclohexyl benzoate—Fischer esterification or reaction of an acid chloride with an alcohol? Explain.

How might you prepare N-methylpropanamide by reaction of an acid chloride with an amine?

Write the mechanism of the reaction just shown between 3,4,5-trimethoxybenzoyl chloride and morpholine to form trimetozine. Use curved arrows to show the electron flow in each step.

How could you prepare the following amides using an acid chloride and an amine or ammonia? (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CONHCH}_{3}\) (b) N,N-Diethylbenzamide (c) Propanamide Equation Transcription: Text Transcription: CH_3CH_2CONHCH_3

How could you prepare the following ketones by reaction of an acid chloride with a lithium diorganocopper reagent?

Write the mechanism of the reaction between p-hydroxyaniline and acetic anhydride to prepare acetaminophen.

What product would you expect from reaction of one equivalent of methanol with a cyclic anhydride, such as phthalic anhydride (1,2-benzenedicarboxylic anhydride)? What is the fate of the second “half” of the anhydride?

Why is the saponification of an ester irreversible? In other words, why doesn’t treatment of a carboxylic acid with an alkoxide ion yield an ester?

What product would you expect from the reaction of butyrolactone with \(\mathrm{LiAlH}_{4}\)? With DIBAH? Equation Transcription: Text Transcription: LiAlH_4

Show the products you would obtain by reduction of the following esters with \(\mathrm{LiAlH}_{4}\): Equation Transcription: Text Transcription: LiAlH4 H3C CH3CH2CH2CHCOCH3

What ester and what Grignard reagent might you start with to prepare the following alcohols? Equation Transcription: Text Transcription: H_3C CH_3 OH H_3C OH OH CH_3CH_2CH_2CH_2CCH_2CH_3 CH_2CH_3

How could you prepare N-ethylaniline by reduction of an amide with \(\mathrm{LiAlH}_{4}\)? Equation Transcription: Text Transcription: LiAlH_4 CH2CH3

How would you convert N-methylbenzamide to each of the following products? (a) Benzoic acid (b) Benzyl alcohol (c) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{NHCH}_{2} \mathrm{CH}_{3}\) Equation Transcription: Text Transcription: C_6H_5CH_2NHCH_2CH_3

How would you use the reaction of an amide with \(\mathrm{LiAlH}_{4}\) as the key step in going from bromocyclohexane to (N,N-dimethylaminomethyl)cyclohexane? Write all the steps in the reaction sequence. Equation Transcription: Text Transcription: LiAlH4 Br CH2N(CH3)2

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: Equation Transcription: Text Transcription: BrCH_2CH_2CH_2Br + HOCH_2CH_2CH_2OH \longrightarrow Base HOCH_2CH_2OH + HO_2C(CH_2)_6CO_2H \longrightarrow H_2SO_4 catalyst H_2N(CH_2)_6NH_2 + ClC(CH_2)_4CCl

Kevlar, a nylon polymer prepared by reaction of 1,4-benzenedicarboxylic acid (terephthalic acid) with 1,4-benzenediamine (p-phenylenediamine), is so strong that it’s used to make bulletproof vests. Draw the structure of a segment of Kevlar.

What kinds of functional groups might compounds have if they show the following IR absorptions? (a) Absorption at \(1735 \mathrm{~cm}^{-1}\) (b) Absorption at 1810 \mathrm{~cm}^{-1}\) (c) Absorptions at 2500 to \(3300 \mathrm{~cm}^{-1} \text { and } 1710 \mathrm{~cm}^{-1}\) (d) Absorption at \(1715 \mathrm{~cm}^{-1}\) Equation Transcription: Text Transcription: 1735 cm-1 1810 cm-1 3300 cm-1 and 1710 cm-1 1715 cm-1

Propose structures for compounds that have the following formulas and IR absorptions: (a) \(\mathrm{C}_{6} \mathrm{H}_{12} \mathrm{O}_{2}, 1735 \mathrm{~cm}^{-1}\) (b) \(\mathrm{C}_{4} \mathrm{H}_{9} \mathrm{NO}, 1650 \mathrm{~cm}^{-1}\) (c) \(\mathrm{C}_{4} \mathrm{H}_{5} \mathrm{ClO}, 1780 \mathrm{~cm}^{-1}\) Equation Transcription: Text Transcription: C6H12O2, 1735 cm-1 C4H9NO, 1650 cm-1 C4H5ClO, 1780 cm-1

Name the following compounds:

How would you prepare the following compounds starting with an appropriate carboxylic acid and any other reagents needed? (Reddish brown = Br.)

The following structure represents a tetrahedral alkoxide-ion intermediate formed by addition of a nucleophile to a carboxylic acid derivative. Identify the nucleophile, the leaving group, the starting acid derivative, and the ultimate product (green = Cl).

Electrostatic potential maps of a typical amide (acetamide) and an acyl azide (acetyl azide) are shown. Which of the two do you think is more reactive in nucleophilic acyl substitution reactions? Explain. Equation Transcription: Text Transcription: H_3C NH_2 H_3C

Predict the product(s) and provide the mechanism for each reaction below. Equation Transcription: Text Transcription: Cl Na^ \overline O OCH_2 CH_3 NH_2 Na^+ \overline O CH_3 B r Na^+ \overline O\mathrmCH

Predict the product(s) and provide the mechanism for each reaction below. Equation Transcription: Text Transcription: HO SOCl2 OH SOCl2 OH SOCl2 HO SOCl2

Predict the product(s) and provide the mechanism for each reaction below. Equation Transcription: Text Transcription: CH_3CH_2O HCl catalyst H_2O OCH_3 HCl catalyst CH_3CH_2OH OH HCl catalyst OH HCl catalyst CH_3CH_2OH

Predict the product(s) and provide the complete mechanism for each reaction below. Equation Transcription: Text Transcription: OCH3 + 2 CH3MgBr H3O+ OCH3 OCH2CH3 + 2 PhMgBr H3O+ O + 2 CH3CH2MgBr H3O+ CO2CH3 + 2 CH3MgBr H3O+

Pivalic mixed anhydrides are often used to form amide bonds between amino acids. Unlike with a symmetrical anhydride, this reaction is highly regioselective, with the nucleophile adding only to the aminoacid carbonyl. Provide the complete mechanism for the reaction below and explain the regioselectivity. Equation Transcription: Text Transcription: NHBoc R1 H2N R2 CO2CH3 BocNH R1 R2 CO2CH3 OH

When 4-dimethylaminopyridine (DMAP) is added in catalytic amounts to acetic anhydride and an alcohol, it significantly increases the rate of ester formation. The process begins with a reaction between acetic anhydride and DMAP to form a highly reactive acetyl pyridinium intermediate that is more reactive than acetic anhydride itself. Propose a mechanism for this process that includes the formation and reaction of the acetyl pyridinium intermediate.

Fats are biosynthesized from glycerol 3-phosphate and fatty-acyl CoA’s by a reaction sequence that begins with the following step. Show the mechanism of the reaction. Equation Transcription: Text Transcription: CH_2OH CHOH CH_2OPO_32- RCSCoA CH_2O-C-R CHOH CH_2OPO_32-

Treatment of an \(\alpha-\text { amino }\) acid with DCC yields a 2,5-diketopiperazine. Propose a mechanism. Equation Transcription: Text Transcription: \alpha- amino H3N+ \alpha- amino

Succinic anhydride yields the cyclic imide succinimide when heated with ammonium chloride at \(200^{\circ} \mathrm{C}\). Propose a mechanism for this reaction. Why do you suppose such a high reaction temperature is required? Equation Transcription: ? ? Text Transcription: 200°C NH_4Cl 200°C N-H+H_2O+HCl

The hydrolysis of a biological thioester to the corresponding carboxylate is often more complex than the overall result might suggest. The conversion of succinyl CoA to succinate in the citric acid cycle, for instance, occurs by initial formation of an acyl phosphate, followed by reaction with guanosine diphosphate (GDP, a relative of adenosine diphosphate [ADP]) to give succinate and guanosine triphosphate (GTP, a relative of ATP). Suggest mechanisms for both steps. Equation Transcription: Text Transcription: CoAS CO2- HOPO32- CO2- CO2- -O

One step in the gluconeogenesis pathway for the biosynthesis of glucose is the partial reduction of 3-phosphoglycerate to give glyceraldehyde 3-phosphate. The process occurs by phosphorylation with ATP to give 1,3-bisphospho glycerate, reaction with a thiol group on the enzyme to give an enzyme-bound thioester, and reduction with NADH. Suggest mechanisms for all three reactions. Equation Transcription: Text Transcription: H-C-OH CH_2OPO_32- OPO_32- H-C-OH CH_2OPO_32- Enz-SH PO_43- H-C-OH S-Enz H-C-OH CH_2OPO_32- NADH/H+ NAD+,Enz-SH H-C-OH CH_2OPO_32-

Bacteria typically develop a resistance to penicillins and other \(\beta \text {-lactam }\) antibiotics (see Something Extra in this chapter) due to bacterial synthesis of \(\beta \text { - lactamase }\) enzymes. Tazobactam, however, is able to inhibit the activity of the \(\beta \text { - lactamase }\) by trapping it, thereby preventing a resistance from developing. (a) The first step in trapping is reaction of a hydroxyl group on the \(\beta \text { - lactamase }\) to open the \(\beta \text {-lactam }\) ring of tazobactam. Show the mechanism. (b) The second step is opening the sulfur-containing ring in tazobactam to give an acyclic imine intermediate. Show the mechanism. (c) Cyclization of the imine intermediate gives the trapped \(\beta \text { - lactamase }\) product. Show the mechanism. Equation Transcription: Text Transcription: \beta-lactam \beta-lactamase \beta-lactamase \beta-lactamase \beta-lactam \beta-lactamase

The following reaction, called the benzilic acid rearrangement, takes place by typical carbonyl-group reactions. Propose a mechanism (Ph = phenyl). Equation Transcription: Text Transcription: NaOH,H_2O H_3O+

In the iodoform reaction, a triiodomethyl ketone reacts with aqueous NaOH to yield a carboxylate ion and iodoform (triiodomethane). Propose a mechanism for this reaction. Equation Transcription: Text Transcription: CI_3 OH- H_2O HCI_3

Give IUPAC names for the following compounds: Equation Transcription: Text Transcription: H_3C NH_2 CH_2CH_3 CH_3CH_2CHCH=CHCCl CH_3OCCH_2CH_2COCH_3 CH_2CH_2COCHCH_3 CH_3 CH_3CHCH_2CNHCH_3 Br COCH_3 SCH(CH_3)_2

Draw structures corresponding to the following names: (a) p-Bromophenylacetamide (b) m-Benzoylbenzamide (c) 2,2-Dimethylhexanamide (d) Cyclohexyl cyclohexanecarboxylate (e) Ethyl 2-cyclobutenecarboxylate (f) Succinic anhydride

Draw and name compounds that meet the following descriptions: (a) Three acid chlorides having the formula \(\mathrm{C}_{6} \mathrm{H}_{9} \mathrm{ClO}\) (b) Three amides having the formula \(\mathrm{C}_{7} \mathrm{H}_{11} \mathrm{NO}\) Equation Transcription: Text Transcription: C6H9ClO C7H11NO

Predict the product, if any, of reaction between propanoyl chloride and the following reagents: (a) \(\mathrm{Li}(\mathrm{Ph})_{2} \mathrm{Cu}\) in ether (b) \(\mathrm{LiAlH}_{4} \text {, then } \mathrm{H}_{3} \mathrm{O}^{+}\) (c) \(\mathrm{CH}_{3} \mathrm{MgBr} \text {, then } \mathrm{H}_{3} \mathrm{O}^{+}\) (d) \(\mathrm{H}_{3} \mathrm{O}^{+}\) (e) Cyclohexanol (f) Aniline (g) \(\mathrm{CH}_{3} \mathrm{CO}_{2}-\mathrm{Na}^{+}\) Equation Transcription: Text Transcription: Li(Ph)2Cu LiAlH4, then H3O+ CH3MgBr, then H3O+ H3O+ CH3CO2 - Na+

Answer Problem 21-48 for reaction of the listed reagents with methylpropanoate.

Answer Problem 21-48 for reaction of the listed reagents with propanamide.

What product would you expect to obtain from Grignard reaction of an excess of phenylmagnesium bromide with dimethyl carbonate, \(\mathrm{CH}_{3} \mathrm{OCO}_{2} \mathrm{CH}_{3}\)? Equation Transcription: Text Transcription: CH3OCO2CH3

How might you prepare the following compounds from butanoic acid? (a) 1-Butanol (b) Butanal (c) 1-Bromobutane (d) Pentanenitrile (e) 1-Butene (f) N-Methylpentanamide (g) 2-Hexanone (h) Butylbenzene (i) Butanenitrile

Predict the product(s) of the following reactions: Equation Transcription: Text Transcription: CO_2CH_2CH_3 CH_3CH2MgBr H_3O+ CH_3 CH_3CHCH_2CH_2CO_2CH_3 H_3O+ COCl CH_3NH_2 CO_2H CH_3 CH_3OH H_2SO_4 CH_3 H_2C=CHCHCH_2CO_2CH3 LiAlH_4 H_3O+ OH CH_3CO_2COCH_3 CONH_2 CH_3 LiAlH_4 H_2O

The following reactivity order has been found for the saponiication of alkyl acetates by aqueous NaOH. Explain. \(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{CH}_{3}>\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}>\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{CH}\left(\mathrm{CH}_{3}\right)_{2}>\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{3}\) Equation Transcription: Text Transcription: CH3CO2CH3 > CH3CO2CH2CH3 > CH3CO2CH(CH3)2 > CH3CO2C(CH3)3

Explain the observation that attempted Fischer esteriication of 2,4,6-trimethylbenzoic acid with methanol and HCl is unsuccessful. No ester is obtained, and the acid is recovered unchanged. What alternative method of esteriication might be successful?

Outline methods for the preparation of acetophenone (phenyl methyl ketone) starting from the following: (a) Benzene (b) Bromobenzene (c) Methyl benzoate (d) Benzonitrile (e) Styrene

Treatment of 5-aminopentanoic acid with DCC (dicyclohexylcarbodiimide) yields a lactam. Show the structure of the product and the mechanism of the reaction.

When ethyl benzoate is heated in methanol containing a small amount of HCl, methyl benzoate is formed. Propose a mechanism for the reaction.

tert-Butoxycarbonyl azide, a reagent used in protein synthesis, is prepared by treating tert-butoxycarbonyl chloride with sodium azide. Propose a mechanism for this reaction. Equation Transcription: Text Transcription: H_3C CH_3 H_3C Cl NaN_3 H_3C CH_3 H_3C N_3 NaCl

The step-growth polymer nylon 6 is prepared from caprolactam. The reaction involves initial reaction of caprolactam with water to give an intermediate open-chain amino acid, followed by heating to form the polymer. Propose mechanisms for both steps, and show the structure of nylon 6.

Qiana, a polyamide fiber with a silky texture, has the following structure. What are the monomer units used in the synthesis of Qiana? Equation Transcription: Text Transcription C(CH_2)_6C-NH CH_2 NH

What is the structure of the polymer produced by treatment of \(\beta \text {-Propiolactone }\) with a small amount of hydroxide ion? Equation Transcription: Text Transcription: \beta -Propiolactone \beta -Propiolactone

Polyimides with the structure shown are used as coatings on glass and plastics to improve scratch resistance. How would you synthesize a polyimide? (See Problem 21-39.)

How would you distinguish spectroscopically between the following isomer pairs? Tell what differences you would expect to see. (a) N-Methylpropanamide and N,N-dimethylacetamide (b) 5-Hydroxypentanenitrile and cyclobutanecarboxamide (c) 4-Chlorobutanoic acid and 3-methoxypropanoyl chloride (d) Ethyl propanoate and propyl acetate

Propose a structure for a compound, \(\mathrm{C}_{4} \mathrm{H}_{7} \mathrm{ClO}_{2}\), that has the following IR and \({ }^{1} \mathrm{HNMR}\) spectra: Equation Transcription: Text Transcription: C_4H_7ClO_2 1H NMR cm-1 \delta

Assign structures to compounds with the following \({ }^{1} \mathrm{HNMR}\) spectra: (a) \(\mathrm{C}_{4} \mathrm{H}_{7} \mathrm{ClO}\) IR: \(1810 \mathrm{~cm}^{-1}\) (b) \(\mathrm{C}_{5} \mathrm{H}_{7} \mathrm{NO}_{2}\) IR: \(2250,1735 \mathrm{~cm}^{-1}\) Equation Transcription: Text Transcription: 1H NMR C_4H_7ClO 1810 cm-1 \delta C_5H_7NO_2 2250, 1735 cm-1 \delta

The following reactivity order has been found for the basic hydrolysis of p-substituted methyl benzoates: \(\mathrm{Y}=\mathrm{NO}_{2}>\mathrm{Br}>\mathrm{H}>\mathrm{CH}_{3}>\mathrm{OCH}_{3}\) How can you explain this reactivity order? Where would you expect \(\mathrm{Y}=\mathrm{C} \equiv \mathrm{N}, \mathrm{Y}=\mathrm{CHO}, \text { and } \mathrm{Y}=\mathrm{NH}_{2}\) to be in the reactivity list? Equation Transcription: Text Transcription: Y = NO_2 > Br > H > CH_3 > OCH_3 Y = CN, Y = CHO, and Y = NH_2 CO_2CH_3 -OH H_2O CO_2- CH_3OH

When a carboxylic acid is dissolved in isotopically labeled water, the label rapidly becomes incorporated into both oxygen atoms of the carboxylic acid. Explain. Equation Transcription: Text Transcription: H_2O

We said in Section 21-6 that mechanistic studies on ester hydrolysis have been carried out using ethyl propanoate labeled with \({ }^{18} \mathrm{O}\) in the ether-like oxygen. Assume that \({ }^{18} \mathrm{O}- labeled\) acetic acid is your only source of isotopic oxygen, and then propose a synthesis of the labeled ethyl propanoate. Equation Transcription: Text Transcription: 18^O 18^O-labeled

Treatment of a carboxylic acid with triluoroacetic anhydride leads to an unsymmetrical anhydride that rapidly reacts with alcohol to give an ester. (a) Propose a mechanism for formation of the unsymmetrical anhydride. (b) Why is the unsymmetrical anhydride unusually reactive? (c) Why does the unsymmetrical anhydride react as indicated rather than giving a trifluoroacetate ester plus carboxylic acid? Equation Transcription: Text Transcription: (CF_3CO)_2O CF_3 R'OH CF_3CO_2H

Butacetin is an analgesic (pain-killing) agent that is synthesized commercially from p-fluoronitrobenzene. Propose a synthesis. Equation Transcription: Text Transcription: NHCOCH_3 (CH_3)_3CO

Phenyl 4-aminosalicylate is a drug used in the treatment of tuberculosis. Propose a synthesis of this compound starting from 4-nitrosalicylic acid. Equation Transcription: Text Transcription: CO_2H O_2N OH H_2N OH

N,N-Diethyl-m-toluamide (DEET) is the active ingredient in many insect-repellent preparations. How might you synthesize this substance from m-bromotoluene? Equation Transcription: Text Transcription: H_3C CH_2CH_3 CH_2CH_3

Tranexamic acid, a drug useful against blood clotting, is prepared commercially from p-methylbenzonitrile. Formulate the steps likely to be used in the synthesis. (Don’t worry about cis–trans isomers; heating to \(300^{\circ} \mathrm{C}\) inter converts the isomers.) Equation Transcription: ? Text Transcription: 300°C H_2NCH_2 CO_2H

One frequently used method for preparing methyl esters is by reaction of carboxylic acids with diazomethane, \(\mathrm{CH}_{2} \mathrm{~N}_{2}\) The reaction occurs in two steps: (1) protonation of diazomethane by the carboxylic acid to yield methyldiazonium ion, \(\mathrm{CH}_{3} \mathrm{~N}_{2}^{+}\), plus a carboxylate ion; and (2) reaction of the carboxylate ion with \(\mathrm{CH}_{3} \mathrm{~N}_{2}^{+}\). (a) Draw two resonance structures of diazomethane, and account for step 1. (b) What kind of reaction occurs in step 2? Equation Transcription: Text Transcription: CH2N2 OH CH2N2 OCH3 N2 CH3N2+ CH3N2+

Draw the structure of the polymer you would expect to obtain from reaction of dimethyl terephthalate with a triol such as glycerol. What structural feature would this new polymer have that was not present in Dacron (Table 21-2)? How do you think this new feature might affect the properties of the polymer?

Assign structures to compounds with the following \({ }^{1} \mathrm{HNMR}\) spectra: (a) \(\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O}_{2}\) IR: \(735 \mathrm{~cm}^{-1}\) (b) \(\mathrm{C}_{11} \mathrm{H}_{12} \mathrm{O}_{2}\) IR: \(1710 \mathrm{~cm}^{-1}\) Equation Transcription: Text Transcription: 1H NMR C5H10O2 735 cm-1 \delta C11H12O2 1710 cm-1 \delta

Propose structures for compounds with the following \({ }^{1} H N M R\) spectra: (a) \(\mathrm{C}_{5} \mathrm{H}_{9} \mathrm{ClO}_{2}\) IR: \(1735 \mathrm{~cm}^{-1}\) (b) \(\mathrm{C}_{7} \mathrm{H}_{12} \mathrm{O}_{4}\) IR: \(1735 \mathrm{~cm}^{-1}\) Equation Transcription: Text Transcription: 1H NMR C5H9ClO2 1735 cm-1 \delta C7H12O4 1735 cm-1 \delta

Propose a structure for the compound with the formula \(\mathrm{C}_{19} \mathrm{H}_{9} \mathrm{NO}_{2}\) and the following IR and NMR spectra Equation Transcription: Text Transcription: C19H9NO2 cm-1 \delta \delta

Draw the structure of the compound that produced the spectra below. The infrared spectrum has strong bands at 1720 and \(1738 \mathrm{~cm}^{-1}\). Equation Transcription: Text Transcription: 1738 cm-1 C7H12O3

When an amide is formed from an acid chloride or an anhydride, two moles of base are required. However, when an ester is used as the starting material, only one equivalent of base is needed. Explain this reactivity in terms of basicity of the leaving groups.

Epoxy adhesives are prepared in two steps. \(S_{N} 2\) reaction of the disodium salt of bisphenol A with epichlorohydrin forms a “prepolymer,” which is then “cured” by treatment with a triamine such as \(\mathrm{H}_{2} \mathrm{NCH}_{2} \mathrm{CH}_{2} \mathrm{NHCH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}\). Draw structures to show how addition of the triamine results in a strengthening of the polymer. Equation Transcription: Text Transcription: SN2 H2NCH2CH2NHCH2CH2NH2 CH3 CH3 H2C-CHCH2Cl H2C-CHCH2 CH3 CH3 CH2CHCH2 CH3 CH3 CH2CH-CH2