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chemistry
organic chemistry

Questions and Answers of Organic Chemistry

If methionine is the first amino acid incorporated into a heptapeptide, what is the sequence of the amino acids encoded for by the following stretch of mRNA? 5ʹ-G-C-A-U-G-G-A-C-C-C-C-G-U-U-A-U-
Draw the structure for each of the following: a. dCDP b. dTTP c. dUMP d. UDP e. guanosine 5ʹ-triphosphate f. adenosine 3ʹ - monophosphate
Write the sequences of bases in the sense strand of DNA that resulted in the mRNA in Problem 18. Problem 18. If methionine is the first amino acid incorporated into a heptapeptide, what is the
List the possible codons on mRNA that specify each amino acid in Problem 18 and the anticodon on the tRNA that carries that amino acid.
Adenine can be deaminated to hypoxanthine, and guanine can be deaminated to xanthine. Draw structures for hypoxanthine and xanthine.
Explain why thymine cannot be deaminated.
Which of the following base sequences would most likely be recognized by a restriction endonuclease? a. ACGCGT b. ACGGGT c. ACGGCA d. ACACGT e. ACATCGT f. CCAACC
What labeled fragments would be obtained from the segment of DNA shown above if a 2ʹ,3ʹ-dideoxy analog of dGTP had been added to the reaction mixture instead of a 2ʹ,3ʹ- dideoxy analog of dATP?
Propose a mechanism for removal of the DMTr protecting group by treatment with acid.
5-Bromouracil, a highly mutagenic compound, is used in cancer chemotherapy. When administered to a patient, it is converted to the triphosphate and incorporated into DNA in place of thymine, which it
Name the following compounds:a.b. c. d.
The hydrolysis of phosphoenolpyruvate is so highly exergonic (ΔG°ʹ = - 14.8 kcal/mol or -61.9kJ/mol) that it can be used to "drive the formation" of ATP from ADP and hydrogen phosphate (ΔG°ʹ =
What would be the base sequence of the segment of DNA that is responsible for the biosynthesis of the following hexapeptide? Gly-Ser-Arg-Val-His-Glu
Propose a mechanism for the following reaction:
Match the codon with the anticodon: Codon Anticodon AAA................. ACC GCA................. CCU CUU................. UUU AGG................. AGG CCU.................
Using the single-letter abbreviations for the amino acids in Table 23.1, write the sequence of amino acids in a polypeptide represented by the first four letters in your first name. Do not use any
Which of the following pairs of dinucleotides are present in equal amounts in DNA? a. CC and GG b. CG and GT c. CA and TG d. CG and AT e. GT and CA f. TA and AT
Why is the codon a triplet rather than a doublet or a quartet?
RNAase, the enzyme that catalyzes the hydrolysis of RNA, has two catalytically active histidine residues at its active site. One of the histidine residues is catalytically active in its acidic form
The amino acid sequences of peptide fragments obtained from a normal protein and from the same protein synthesized by a defective gene were compared. They were found to differ in only one peptide
Whether the mechanism requiring activation of a carboxylate ion by ATP involves attack of the carboxylate ion on the α-phosphorus or the -phosphorus of ATP cannot be determined from the reaction
Why is pyruvate a good leaving group?
What would be the results of the experiment in Problem 39 if radioactive AMP were added to the incubation mixture instead of radioactive pyrophosphate?
Which cytosine in the following sense strand of DNA could cause the most damage to the organism if it were deaminated? 5ʹ-A-T-G-T-C-G-C-T-A-A-T-C-3ʹ
Sodium nitrite, a common food preservative (p. 000), is capable of causing mutations in an acidic environment by converting cytosines to uracils. Explain how this occurs.
The first amino acid incorporated into a polypeptide chain during its biosynthesis in prokaryotes is N-formylmethionine. Explain the purpose of the formyl group.
Several important biomolecules and the ΔG° values for their hydrolysis are listed here. Which of them "hydrolyzes" with sufficient energy to "drive the formation" of ATP? Glycerol-1-phosphate: -2.2
The β-phosphorus of ATP has two phosphoanhydride linkages, but only the one linking the β-phosphorus to the -phosphorus is broken in phosphoryl transfer reactions. Explain why the one linking the
ATP has pKa values of 0.9, 1.5, 2.3, and 7.7; ADP has pKa values of 0.9, 2.8, and 6.8; and phosphoric acid has pKa values of 1.9, 6.7, and 12.4. Do the calculation showing that at pH 7.3: a. The
What products would be obtained from the hydrolysis of cyclic AMP?
Indicate whether each functional group of the five heterocyclic bases in nucleic acids can function as a hydrogen bond acceptor (A), a hydrogen bond donor (D), or both (D/A).
What monomer would you use to form each of the following polymers?a.b. c. ¬CF2CF2CF2CF2CF2CF2CF2CF2CF2CF2-
Describe the polymerization of 2,2-dimethyloxirane a. By an anionic mechanism b. By a cationic mechanism
Which monomer and which type initiator would you use to synthesize each of the following polymers?a.b. c. ¬CH2CH2OCH2CH2O¬ d.
Draw a short segment of the polymer formed from cationic polymerization of 3,3- dimethyloxacyclobutane.
The polymer formed from a diene such as 1,3-butadiene contains vinyl branches. Propose an anionic polymerization mechanism to account for the formation of these branches.
a. Draw a short segment of nylon 4. b. From what lactam is nylon 4 synthesized? c. Draw a short segment of nylon 44.
Write an equation that explains what will happen if a scientist working in the laboratory spills sulfuric acid on her nylon 66 hose.
What happens to polyester slacks if aqueous NaOH is spilled on them?
a. Propose a mechanism for the formation of the prepolymer formed by bisphenol A and epichlorohydrin. b. Propose a mechanism for the reaction of the prepolymer with the hardener.
If a small amount of glycerol is added to the reaction mixture of toluene-2,6-diisocyanate and ethylene glycol during the synthesis of polyurethane foam, a much stiffer foam is obtained. Explain.
Which polymer would be more apt to contain abnormal head-to-head linkages: poly(vinyl chloride) or polystyrene?
Propose a mechanism for the formation of Melmac®.
Bakelite was the first of the thermosetting polymers. It is a highly cross-linked polymer formed from the acid-catalyzed polymerization of phenol and formaldehyde. It is a much darker polymer than
Draw short segments of the polymers obtained from the following monomers:a.CH2=CHFb. CH2=CHCO2Hc.d. e.
Draw the repeating unit of the step-growth polymer that will be formed from each of the following reactions:a.b. c. d.
Draw the structure of the monomer or monomers used to synthesize the following polymers:a.b. c. d. e. f. g. h. For each polymer, indicate whether it is a chain-growth polymer or a step-growth polymer.
Explain why the configuration of a polymer of isobutylene is not isotactic, syndiotactic, or atactic.
Draw short segments of the polymers obtained from the following compounds under the given reaction conditions:a.b. c. d. e. f.
Quiana® is a synthetic fabric that feels very much like silk.a. Is Quiana® a nylon or a polyester?b. What monomers are used to synthesize Quiana®?
Explain why a random copolymer is obtained when 3,3-dimethyl-1-butene undergoes cationic polymerization.
Polly Propylene has started two polymerization reactions. One flask contains a monomer that polymerizes by a chain-growth mechanism, and the other flask contains a monomer that polymerizes by a
Draw a segment of polystyrene that contains abnormal head-to-head and tail-to-tail linkages.
Poly(vinyl alcohol) is a polymer used to make fibers and adhesives. It is synthesized by hydrolysis or alcoholysis of the polymer obtained from polymerization of vinyl acetate.a. Why is poly(vinyl
Five different repeating units are found in the polymer obtained by cationic polymerization of 4-methyl-1-pentene. Identify these repeating units.
If a peroxide is added to styrene, the polymer known as polystyrene is formed. If a small amount of 1,4-divinylbenzene is added to the reaction mixture, a stronger and more rigid polymer is formed.
A particularly strong and rigid polyester used for electronic parts is marketed under the trade name Glyptal®. It is a polymer of terephthalic acid and glycerol. Draw a segment of the polymer, and
Draw a short section of the polymer obtained from anionic polymerization of Î²-propiolactone.
Which monomer would give a greater yield of polymer, 5-hydroxypentanoic acid or 6-hydroxyhexanoic acid? Explain your choice.
When rubber balls and other objects made of natural rubber are exposed to the air for long periods, they turn brittle and crack. This does not happen to objects made of polyethylene. Explain.
Why do vinyl raincoats become brittle as they get old, even if they are not exposed to air or to any pollutants?
The polymer shown here is synthesized by hydroxide ion-promoted hydrolysis of an alternating copolymer of para-nitrophenyl methacrylate and acrylate.a. Propose a mechanism for the formation of the
An alternating copolymer of styrene and vinyl acetate can be turned into a graft copolymer by hydrolyzing it and then adding ethylene oxide. Draw the structure of the graft copolymer.
Show the mechanism for the formation of a segment of poly(vinyl chloride) containing three units of vinyl chloride and initiated by hydrogen peroxide.
How could head-to-head poly(vinyl bromide) be synthesized?
Delrin® (polyoxymethylene) is a tough self-lubricating polymer used in gear wheels. It is made by polymerizing formaldehyde in the presence of an acid catalyst. a. Propose a mechanism for formation
Draw a short segment of branched polystyrene that shows the linkages at the branch point.
List the following groups of monomers in order of decreasing ability to undergo cationic polymerization:a.b. c.
List the following groups of monomers in order of decreasing ability to undergo anionic polymerization:a.b. CH2 = CHCH3 CH2 = CHCl CH2 = CHC ‰¡ N
Explain why when propylene oxide undergoes anionic polymerization, nucleophilic attack occurs at the less substituted carbon of the epoxide, but when it undergoes cationic polymerization,
Examine the following pericyclic reactions. For each reaction, indicate whether it is an electrocyclic reaction, a cycloaddition reaction, or a sigmatropic rearrangement.
Compare the reaction of 2,4,6-cycloheptatrienone with cyclopentadiene to that with ethene. Why does 2,4,6-cycloheptatrienone use two Ï€ electrons in one reaction and four Ï€
a. Name the kind of sigmatropic rearrangement that occurs in each of the following reactions.b. Using arrows show the electron rearrangement that takes place in each of the reactions.1.2. 3. 4.
Give the product of the following reaction:If the terminal sp2 carbon of the substituent bonded to the benzene ring is labeled with 14C, where will the label be in the product?
Account for the difference in the products obtained under photochemical and thermal conditions.
5-Methyl-1,3-cyclopentadiene rearranges to give a mixture of 5-methyl-1,3-cyclopentadiene, 1-methyl-1,3-cyclopentadiene, and 2-methyl-1,3-cyclopentadiene. Show how these products are formed.
[1,3] Sigmatropic migrations of hydrogen cannot occur under thermal conditions, but [1,3] sigmatropic migrations of carbon can occur under thermal conditions. Explain.
a. Will thermal 1,3-migrations of carbon occur with retention or inversion of configuration? b. Will thermal 1,5-migrations of carbon occur with retention or inversion of configuration?
Answer the following questions for the π molecular orbitals of 1,3,5-hexatriene: a. Which are the bonding orbitals, and which are the antibonding orbitals? b. Which orbitals are the HOMO and the
Explain why photochemical ring closure of provitamin D3 to form 7-dehydrocholesterol results in the hydrogen and methyl substituents being trans to one another.
Give the product of each of the following reactions:a.b. c. d. e. f. g. h.
Give the product of each of the following reactions:a.b. c. d.
Chorismate mutase is an enzyme that promotes a pericyclic reaction by forcing the substrate to assume the conformation needed for the reaction. The product of the pericyclic reaction is prephenate,
Account for the difference in the products of the following reactions:
Show how norbornane could be prepared from cyclopentadiene.
Give the product formed when each of the following compounds undergoes an electrocyclic reactiona. Under thermal conditionsb. Under photochemical conditions1.2.
Give the product of each of the following reactions:a.b. c. d. e.
Which is the product of the following [1, 3] sigmatropic rearrangement, A or B?
Dewar benzene is a highly strained isomer of benzene. In spite of its thermodynamic instability, it is very stable kinetically. It will rearrange to benzene, but only if heated to a very high
a. How many π molecular orbitals does 1,3,5,7-octatetraene have? b. What is the designation of its HOMO (ψ1, ψ2, etc.)? c. How many nodes does its highest-energy π molecular orbital have between
If the following compounds are heated, one will form one product from a [1, 3] sigmatropic rearrangement and the other will form two products from two different [1, 3] sigmatropic rearrangements.
When the following compound is heated, a product is formed that shows an infrared absorption band at 1715 cm-1. Draw the structure of the product.
Two products are formed in the following [1, 7] sigmatropic rearrangement, one due to hydrogen migration and the other to deuterium migration. Show the configuration of the products by replacing A
a. Propose a mechanism for the following reaction.b. What would be the reaction product if trans-2-butene were used instead of ethene?
Explain why two different products are formed from disrotatory ring closure of (2E, 4Z, 6Z) octatriene, but only one product is formed from disrotatory ring closure of (2E, 4Z, 6E)-octatriene.
Give the product of each of the following sigmatropic rearrangements:a.b. c. d.
cis-3,4-Dimethylcyclobutene undergoes thermal ring opening to form the two products shown. One of the products is formed in 99% yield, the other in 1% yield. Which is which?
If isomer A is heated to about 100 °C, a mixture of isomers A and B is formed. Explain why there is no trace of isomer C or D.
Propose a mechanism for the following reaction:
Compound A will not undergo a ring-opening reaction under thermal conditions, but compound B will. Explain.

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