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organic chemistry

Questions and Answers of Organic Chemistry

Which compound would you expect to have the higher melting point, propane or cyclopropane? Explain your answer.
Which amines in Practice Problem 2.16 are(a) Primary amines,(b) Secondary amines,(c) Tertiary amines?Problem 2.16(a)(b)(c)(d) Me エーZ: IN
Cyclobutadiene (below) is like benzene in that it has alternating single and double bonds in a ring. However, its bonds are not the same length, the double bonds being shorter than the single bonds;
In Chapter 15 we shall learn how the nitronium ion, NO2+, forms when concentrated nitric and sulfuric acids are mixed.(a) Write a Lewis structure for the nitronium ion.(b) What geometry does VSEPR
What do the bond angles of beryllium hydride suggest about the hybridization state of the beryllium atom?
What do the bond angles of boron trifluoride suggest about the hybridization state of the boron atom?
What do the bond angles of water suggest about the hybridization state of the oxygen atom of water?
What do the bond angles of ammonia suggest about the hybridization state of the nitrogen atom of ammonia?
Which molecules in Practice Problem 1.14 form sets of constitutional isomers?Problem 1.14(a) (CH3)2CHCH2CH3(b) (CH3)2CHCH2CH2OH(c) (CH3)2C=CHCH2CH3(d) CH3CH2CH2CH2CH3(e) CH3CH2CH(OH)CH2CH3(f)
There are actually three constitutional isomers with the molecular formula C3H8O. We have seen two of them in propyl alcohol and isopropyl alcohol. Write a dash formula for the third isomer.
Write a Lewis structure for the phosphate ion (PO43-).
Write a dash structural formula showing all valence electrons for CH3CHO (acetaldehyde).
Write the Lewis structure of CH3OH.
Using the periodic table, which element in each pair is more electronegative?(a) Si, O(b) N, C(c) Cl, Br(d) S, P
What accounts for the ease of imine formation between penicillinase and the sulfone antibiotic that counteracts penicillin resistance?
What is the chemical name of each of the following drugs?a. Benzocaineb. Procaine
Show the steps involved in the following reaction: CO,CH3 CO,CH3 + || + CO2 CO,CH3 CO,CH3
Does the [1,7] sigmatropic rearrangement that converts provitamin D3 to vitamin D3 involve suprafacial or antarafacial rearrangement?
Why was a deuterated compound used in the preceding example?
Will a concerted reaction take place between 1,3-butadiene and 2-cyclohexenone in the presence of ultraviolet light?
a. Identify the mode of ring closure for each of the following electrocyclic reactions.b. Are the indicated hydrogens cis or trans?1.2. H A, H
Which of the following are correct? Correct any false statements.a. A conjugated diene with an even number of double bonds undergoes conrotatory ring closure under thermal conditions.b. A conjugated
Draw a short segment of gutta-percha.
Polyethylene can be used for the production of beach chairs and beach balls. Which of these items is made from more highly branched polyethylene?
What nonapeptide is coded for by the following piece of mRNA?5'-AAA-GUU-GGC-UAC-CCC-GGA-AUG-GUG-GUC-3'
UAA is a stop codon. Why does the UAA sequence in mRNA in Problem 18 not cause protein synthesis to stop?
Four C’s occur in a row in the segment of mRNA in Problem 18. What polypeptide would be formed from the mRNA if one of the four C’s were cut out of the strand?Problem 18If methionine is the first
If one of the strands of DNA has the following sequence of bases running in the 5' → 3' direction,
Is the OH substituent of the A ring of cholesterol an α-substituent or a β-substituent?
A β-hydrogen at C-5 means that the A and B rings are _____ fused; an α-hydrogen at C-5 means that they are _____ fused.
Membranes contain proteins. Integral membrane proteins extend partly or completely through the membrane, whereas peripheral membrane proteins are found on the inner or outer surface of the membrane.
Serine proteases do not catalyze hydrolysis if the amino acid at the hydrolysis site is a D-amino acid. Trypsin, for example, cleaves on the C-side of L-Arg and L-Lys, but not on the C-side of D-Arg
What causes the mode of catalysis to change from general base to nucleophilic in the hydrolysis of an ortho carboxyl-substituted phenyl acetate?
The rate constant for the uncatalyzed reaction of two molecules of glycine ethyl ester to form glycylglycine ethyl ester is 0.6 s-1 M-1. In the presence of [Co(ethylenediamine)2]2+, the rate constant
An alcohol will not react with aziridine unless the reaction is catalyzed by an acid. Why is a catalyst necessary? H HCl H;NCH,CH,OCH; CI CH;OH aziridine
Which of the following parameters would be different for a reaction carried out in the presence of a catalyst, compared with the same reaction carried out in the absence of a catalyst? ΔG , ΔΗ,
How would a protein that resides in the interior of a membrane fold, compared with the water-soluble protein just discussed?
Determine the amino acid sequence of a polypeptide from the following results:Acid hydrolysis gives Ala, Arg, His, 2 Lys, Leu, 2 Met, Pro, 2 Ser, Thr, Val.Carboxypeptidase A releases Val.Edman’s
In determining the primary structure of insulin, what would lead you to conclude that it had more than one polypeptide chain?
Suppose you are trying to synthesize the dipeptide Val-Ser. Compare the product that would be obtained if the carboxyl group of N-protected valine were activated with thionyl chloride with the
a. How many different octapeptides can be made from the 20 naturally occurring amino acids?b. How many different proteins containing 100 amino acids can be made from the 20 naturally occurring amino
A mixture of seven amino acids (glycine, glutamate, leucine, lysine, alanine, isoleucine, and aspartate) is separated by TLC. Explain why only six spots show up when the chromatographic plate is
Why are the carboxylic acid groups of the amino acids so much more acidic (pKa ~ 2) than a carboxylic acid such as acetic acid (pKa = 4.76)?
Which amino acids in Table 23.1 have more than one asymmetric carbon?Table 23.1 The Most Common Naturally Occurring Amino Acids The amino acids are shown in the form that predominates at
What kind of aldohexose would form L-glyceraldehyde when its acetal is oxidized with periodic acid?
Aldohexoses A and B form the same osazone. A is oxidized by nitric acid to an optically active aldaric acid, and B is oxidized to an optically inactive aldaric acid. Ruff degradation of either A or B
What two monosaccharides can be degraded toa. D-arabinose?b. D-glyceraldehyde?c. L-ribose?
What monosaccharides would be formed in a Kiliani–Fischer synthesis starting with one of these?a. D-xyloseb. L-threose
What monosaccharides form the same osazone as D-sorbose?
What products are obtained from the reduction ofa. D-idose?b. D-sorbose?
a. What sugar is the C-3 epimer of D-xylose?b. What sugar is the C-5 epimer of D-allose?c. What sugar is the C-4 epimer of L-gulose?
a. Are D-erythrose and L-erythrose enantiomers or diastereomers?b. Are L-erythrose and L-threose enantiomers or diastereomers?
Classify the following monosaccharides: CH,OH C=0 HC=0 HC-O НО -H Н— ОН ОН OH Но- Но- H- H- -H- -- OH ОН H-OH -ОН H- -O- ČH,OH ČH,OH D-sedoheptulose ČH,OH D-ribose D-mannose HH HHH
Compare the mechanisms of the following reactions: NH2 + NH2 + CI `N CI NH, NH, + CF
A compound forms cis-1,2-dimethycyclopropane when it is reduced with H2 and Pd/C. The 1H NMR spectrum of the compound shows only two singlets. What is the structure of the compound?
Upon treatment with ozone followed by work-up with hydrogen peroxide, an alkene forms formic acid and a compound that shows three signals (a singlet, a triplet, and a quartet) in its 1H NMR spectrum.
Identify A–N: 1. CH3CCI AlCl3 2. H20 RČOOH A HCI C+D H20 Br2 Soclz E+F CH3I 1. LIAIHĄ H 2. H20 excess NH3 G K2CO3 Ag20 1. Оз, -78°C K L+M 2. H202
How many different functional groups can you use to synthesize a primary alcohol?
What aspect of the structure of the alkene does ozonolysis not tell you?
What alkyl bromide should be used in the acetoacetic ester synthesis of each of the following methyl ketones?a. 2-pentanoneb. 2-octanonec. 4-phenyl-2-butanone
What compound is formed when cyclohexanone is shaken with NaOD D2O in for several hours?
Explain why the aldehydic hydrogen (the one attached to the carbonyl carbon) is not exchanged with deuterium. -OD CH;CH CD;CH D20
How can the following compounds be prepared, starting with a carbonyl compound with one fewer carbon atoms than the desired product?a. HOCH2CH2NH2b. CH3CHČOH ОН
Name the following compounds:a.b.c. CH;CHCH,CH,ĈCH,CH3 OH
Why are numbers not used to designate the positions of the functional groups in propanone and butanedione?
a. Which of the following reactions will not give the carbonyl product shown?1.2.3.4.5.6.7.8.9.10.b. Which of the reactions that do not occur can be made to occur if an acid catalyst is added to the
a. Which of the following reactions will not give the carbonyl product shown?1.2.3.4.5.6.7.8.9.10. LI CH;COČCH3 CH;COH + CH;CO
An oil obtained from coconuts is unusual in that all three fatty acid components are identical. The molecular formula of the oil is C45H86O6. What is the molecular formula of the carboxylate ion
Early chemists could envision several possible mechanisms for hydroxide-ion-promoted ester hydrolysis:1. a nucleophilic acyl substitution reaction2. An SN2 reaction3. An SN1 reactionDevise an
D. N. Kursanov, a Russian chemist, proved that the bond that is broken in the hydroxideion- promoted hydrolysis of an ester is the acyl C-O bond, rather than the alkyl C-O bond, by studying the
a. List the following esters in order of decreasing reactivity toward hydrolysis:b. How would the rate of hydrolysis of the para-methylphenyl ester compare with the rate of hydrolysis of these three
a. Two amides are obtained from the reaction of acetyl chloride with a mixture of ethylamine and propylamine. Identify the amides.b. Only one amide is obtained from the reaction of acetyl chloride
The word “lactone” has its origin in lactic acid, a three-carbon carboxylic acid with an OH group on the a-carbon. Ironically, lactic acid cannot form a lactone. Why not?
a. List the following compounds in order of decreasing reactivity toward nucleophilic aromatic substitution:chlorobenzene 1-chloro-2,4-dinitrobenzene
Explain why HBr should be used to generate the benzenediazonium salt if bromobenzene is the desired product of the Sandmeyer reaction and HCl should be used if chlorobenzene is the desired product.
Investigation has shown that cyclobutadiene is actually a rectangular molecule rather than a square molecule. In addition, it has been established that there are two different
The principle of least motion, which states that the reaction that involves the least change in atomic positions or electronic configuration (all else being equal) is favored, has been suggested to
In a reaction called the Birch reduction, benzene can be partially reduced to 1,4-cyclohexadiene by an alkali metal (Na, Li, or K) in liquid ammonia and a low-molecular-weight alcohol. Propose a
The two hydrogens of a methylene group adjacent to an asymmetric carbon are not equivalent hydrogens because they are in different environments due to the asymmetric carbon. (You can verify this
a. Calculate the ratios of the different kinds of protons in a compound with an integral ratio of 6 : 4 : 18.4 (going from left to right across the spectrum).b. Determine the structure of a compound
Where would you expect to find the 1H NMR signal of (CH3)2Mg relative to the TMS signal? (See Table 12.3.)Table 12.3 The Electronegativities of Some of the Elementsa IA IIA IB IIB А IVA VA VIA VIIA
How could you distinguish the 1H NMR spectra of the following compounds?a. CH3OCH2OCH3b. CH3OCH3c. CH3 CH3OCH,CCH2OCH3 ČH3
How many signals would you expect to see in the 1H NMR spectrum of each of the following compounds?a. CH3CH2CH2CH3b. BrCH2CH2Brc. CH2=CHCld. e.f.g.h.i.j.k.l.m.n.o. CH2=CHCH
Which of the following compounds has a vibration that is infrared inactive: acetone, 1-butyne, 2-butyne, H2, H2O, Cl2, ethene?
The mass spectra of two very stable cycloalkanes both show a molecular ion peak atm/z = 98. One spectrum shows a base peak at m/z = 69, the other shows a base peak atm/z = 83. Identify the
The organoborane used in a Suzuki reaction is prepared by the reaction of catecholborane with an alkene or an alkyne.What hydrocarbon would you use to prepare the organoborane of Problem 35?Problem
Explain why tertiary alkyl halides cannot be used in coupling reactions with Gilman reagents.
Which of the following reactions will occur? (For the pKa values necessary to do this problem, see Appendix II.) H20 CH4 HOMGB. CH;OH CH4 + CH3OMGBR CH3MGB NH3 CH4 + H2NMgBr CH3MGB CH3NH2 CH4 CH;NMGB
Show, using any necessary reagents, how the following compounds could be prepared with ethylene oxide as one of the reactants:a. CH3CH2CH2CH2OHb. CH3CH2CH2CH2Dc. CH3CH2CH2CH2Brd. CH3CH2CH2CH2CH2CH2OH
Explain why the ether obtained by treating an optically active alcohol with PBr3 followed by sodium methoxide has the same configuration as the alcohol, whereas the ether obtained by treating the
Why isn’t a cumulated diene formed in the preceding reaction?
a. What products (including stereoisomers if applicable) would be formed from the reaction of 3-bromo-2-methylpentane with HO- under SN2/E2 conditions and under SN1/El conditions?b. Answer the same
Identify the three products that are formed when 2-bromo-2-methylpropane is dissolved in a mixture of 80% ethanol and 20% water.
Would you expect methoxide ion to be a better nucleophile if it were dissolved in CH3OH or if it were dissolved in dimethyl sulfoxide (DMSO)? Why?
The pKa of acetic acid in water is 4.76 (Section 1.17). What effect would a decrease in the polarity of the solvent have on the pKa? Why?
Would you expect acetate ion (CH3CO2-) to be a more reactive nucleophile in an SN2 re-action carried out in methanol or in dimethyl sulfoxide?
Most of the pKa values given throughout this text are values determined in water. How would the pKa values of the following classes of compounds change if they were deter-mined in a solvent less
What product is obtained when ethylamine reacts with excess methyl iodide in a basic solution of potassium carbonate? K,CO3 CH;CH,NH, + CH3-I excess
List the following species in order of decreasing nucleophilicity in an aqueous solution: CH;OH HO CH;CO CH3S
a. Which is a stronger base, RO- or RS-?b. Which is a better nucleophile in an aqueous solution?

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