(a)
Interpretation:
The synthesis of given compound from the given starting material is to be stated.
Concept Introduction:
Amino group reacts faster with the
Answer to Problem 27.71AP
The synthesis of given compound from the given starting material is shown below.
Explanation of Solution
The given reaction is shown below.
Figure 1
The amine group of the
Figure 2
The complete synthesis of the given compound is shown in Figure 2.
(b)
Interpretation:
The synthesis of given compound from the given starting material is to be stated.
Concept Introduction:
Sodium borohydride is a strong reducing agent. The hydride ion of sodium borohydride acts as the nucleophile and gets attached to the carbonyl carbon.
Answer to Problem 27.71AP
The synthesis of given compound from the given starting material is shown below.
Explanation of Solution
The given reaction is shown below.
Figure 3
The benzoic acid reacts with
Figure 4
The complete synthesis of the given compound is shown in Figure 4.
(c)
Interpretation:
The synthesis of given compound from the given starting material is to be stated.
Concept Introduction:
Aldehydes reacts with sodium cyanide to form nitrile compound. The nitrile compound reacts with ammonium chloride to form the
Answer to Problem 27.71AP
The synthesis of given compound from the given starting material is shown below.
Explanation of Solution
The given reaction is shown below.
Figure 5
The deuteriated acetaldehyde reacts with ammonium chloride and sodium cyanide to form deuteriated
Figure 6
The synthesis of the given compound is shown in Figure 6.
(d)
Interpretation:
The synthesis of given compound from the given starting material is to be stated.
Concept Introduction:
Amino group reacts faster with the alkyl halides than the carboxylic group. The reaction of carboxylic acid can be performed only by protecting the amine group. Fmoc compound is used as the protecting agent for amine group. Amine and acid chloride reacts to form amide bond.
Answer to Problem 27.71AP
The synthesis of given compound from the given starting material is shown below.
Explanation of Solution
The given reaction is shown below.
Figure 7
The cesium salt of Fmoc-proline is reacted with the resin linker. The amine is deprotecteed in pyrrolidine. Fmoc-alanine reacts with the prolin resin in presence of
Figure 8
The alanine-proline resin reacts with the Boc protected lysin to form the
Figure 9
Figure 10
The synthesis of the given compound is shown in Figure 8 and Figure 9 and Figure 10.
(e)
Interpretation:
The synthesis of given compound from the given starting material is to be stated.
Concept Introduction:
Aldehydes reacts with sodium cyanide to form nitrile compound. The nitrile compound reacts with ammonium chloride to form the
Answer to Problem 27.71AP
The complete synthesis of given compound is shown below.
Explanation of Solution
The given reaction is shown below.
Figure 11
The compound
Figure 12
The synthesis of the given compound is shown in Figure 12.
(f)
Interpretation:
The synthesis of given compound from the given starting material is to be stated.
Concept Introduction:
The
Answer to Problem 27.71AP
The complete synthesis of given compound is shown below.
Explanation of Solution
The given reaction is shown below.
Figure 13
The compound cyclopentene undergo bromination reaction to form
Figure 14
The given nitrile compound upon reaction with sodium ethoxide forms anion. The formed anion reacts with
Figure 15
The complete synthesis of given compound is shown in Figure 14 and Figure 15.
(g)
Interpretation:
The synthesis of given compound from the given starting material is to be stated.
Concept Introduction:
The reaction of carboxylic acid and amines to form amide is not possible. Amines are very basic so it abstracts acidic proton from the carboxylic acid. The reaction is performed in the presence of
Answer to Problem 27.71AP
The complete synthesis of given compound is shown below.
Explanation of Solution
The given reaction is shown below.
Figure 16
The reaction between terephthalic acid and
Figure 17
The synthesis of given compound is shown in Figure 17.
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Chapter 27 Solutions
Organic Chemistry
- An amino acid mixture of phenylalanine, glycine and glutamic acid is to be separated bypaper chromatography. The solvent is less polar than water. Which of these amino acids will have the highest Rf value and which the lowest? Explain. Treatment of a new protein with dansyl chloride reveals two (2) dansyl-labelled derivatives of amino acids, alanine and methionine. What can you deduce about the structure of the protein from these results? Name the amino acids that contribute atoms to both purine and pyrimidine rings.arrow_forwardBy using only amide/Peptide bond forming rxn and a lKylation rxns. Provide all the reaction steps with the reagent needed and conditions with out showing the mechanism for each step to form the product. Note: Use protecting groups like (Boc, Fmoc, and others) H2NNH2+arrow_forwardUsing the information below, determine the amino acid sequence of the peptide, and explain how your structure is consistent with each piece of information. Complete hydrolysis by 6 M HCl at 110°C followed by amino acid analysis indicated the presence of Gly, Leu, Phe, and Tyr in a 2:1:1:1 molar ratio. Treatment of the peptide with1-fluoro-2,4-dinitrobenzene followed by complete hydrolysis and chromatography indicated the presence of the 2,4-dinitrophenyl derivative of tyrosine. No free tyrosine could be found. Complete digestion of he peptide with pepsin (which cleaves on the amino side of aromatic residues) followed by chromatography yielded a dipeptide containing Phe and Leu and a tripeptide containing Tyr and Gly in a 1:2 ratio.arrow_forward
- The BOC-protecting group may be added by treatment of an amino acid with di-tert- butyl dicarbonate as shown in the following reaction sequence. Propose a mechanism to account for formation of these products. (CH3),COCOČOC(CH3), + H2NCHCOO- (CH),COČNHCHCOO-+ (CH,),COH + CO, Di-tert-butyl dicarbonate BOC-amino acidarrow_forward7. Determine the net charge at pH 6 on each peptide shown below. The pKa's of relevant side chain functionality are given. The pKa of the NH groups within the backbones of the rings is about 20. pK₂= 10 HO NH3 pk₂ = 11 -NH pK₂=4 HO- NH NH -NH HN HN HN SH pk₂ = 8 Net charge:arrow_forwardProtein: SHAYNERSE Predict the products of the following reactions with the protein given, if there is none, write NO RXN. - Biuret reagent - KOH/Pb(CH2COO)2 - Glyoxilic Acid/Conc. H2SO - Hg/HNO3 - HNO3arrow_forward
- in the synthesis of benzocaine: explain how any unreacted p-aminobenzoic acid was removed in the reaction workup.arrow_forwardTreatment of a new protein with dansyl chloride reveals two (2) dansyl-labelled derivatives of amino acids, alanine and methionine. What can you deduce about the structure of the proteinfrom these results?arrow_forwardDetermine the amino acid sequence of a polypeptide from the following data: Acid-catalyzed hydrolysis gives Ala, Arg, His, 2 Lys, Leu, 2 Met, Pro, 2 Ser, Thr, and Val. Carboxypeptidase A releases Val. Edman’s reagent releases PTH-Leu. Treatment with cyanogen bromide gives three peptides with the following amino acid compositions: 1. His, Lys, Met, Pro, Ser 2. Thr, Val 3. Ala, Arg, Leu, Lys, Met, Ser Trypsin-catalyzed hydrolysis gives three peptides and a single amino acid: 1. Arg, Leu, Ser 2. Met, Pro, Ser, Thr, Val 3. Lys 4. Ala, His, Lys, Metarrow_forward
- Histamine is synthesized from one of the 20 protein-derived amino acids. Suggest which amino acid is its biochemical precursor and the type of organic reaction(s) involved in its biosynthesis (e.g., oxidation, reduction, decarboxylation, nucleophilic substitution). CH,CH,NH, H. Histaminearrow_forwardPredict the charge. on the predominant species of the peptide E-D-K-R-A-S-T at pH 5.0. charge:arrow_forwardA chemically modified guanidino group is present in cimetidine (Tagamet), a widely prescribed drug for the control of gastric acidity and peptic ulcers. Cimetidine reduces gastric acid secretion by inhibiting the interaction of histamine with gastric H, recep- tors. In the development of this drug, a cyano group was added to the substituted gua- nidino group to alter its basicity. Do you expect this modified guanidino group to be more basic or less basic than the guanidino group of arginine? Explain. N-CN H,C CH,SCH,CH,NHËNHCH, HN, Cimetidine (Tagamet)arrow_forward