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chemistry
organic chemistry

Questions and Answers of Organic Chemistry

Which of the compounds in Exercise 14 exhibit cis-trans isomerism?
Consider the following four structures:a. Which of these compounds have the same physical properties (melting point, boiling point, density, and so on)? b. Which of these compounds are trans
Alkenes and cycloalkanes are structural isomers of each other. Give an example of each using C4H8. Another common feature of alkenes and cycloalkanes is that both have restricted rotation about one
Cis-trans isomerism is also possible in molecules with rings. Draw the cis and trans isomers of 1,2-dimerhyl- cyclohexane.
Draw the following. a. Ds-2-hexene b. Trans-2-burene c. Cis-2,3-dichloro-2-pentene
Draw all the structural and geometric (cis-trans) isomers of C3H5CI.
Draw all the structural and geometric (cis-trans) isomers of C4H7F.
Draw all the structural isomers of C5H10. Ignore any cyclic isomers. Which of the structural isomers exhibit cis-trans isomerism?
Draw all the structural and geometric (cis-trans) isomers of bromochloropropene.
Name the following compounds.a.b. c.
If one hydrogen in a hydrocarbon is replaced by a halogen atom, the number of isomers that exist for the substituted compound depends on the number of types of hydrogen in the original hydrocarbon.
Polychlorinated dibenzo-p-dioxins, or PCDDs, are highly toxic substances that are present in trace amounts as byproducts of some chemical manufacturing processes. They have been implicated in a
Carboxylic acids are often written as RCOOH. What does —COOH indicate, and what does R indicate? Aldehydes are sometimes written as RCHO. What does —CHO indicate?
Alcohols and ethers are structural isomers of each other, as are aldehydes and ketones. Give an example of each to illustrate. Which functional group in Table can be structural isomers of carboxylic
Identity each of the following compounds as a carboxylic acid, ester, ketone, aldehyde, or amine, a. anthraquinone, an important starting material in the manufacture of dyes:b. c. d.
Identify' the functional groups present in the following compounds.a.b. c.
Mimosine is a natural product found in large quantities in the seeds and foliage of some legume plants. It has been shown to cause inhibition of hair growth as well as hair loss in mice.a. What
Minoxidil (C9H15N5O) is a compound produced by the Pharmacia & Upjohn Company that has been approved as a treatment for some types of male pattern baldness.
For each of the following alcohols, give the systematic name and specif)€™ whether the alcohol is primary, sec-ondary, or tertiary.a.b. c.
Draw structural formulas for each of the following alcohols. Indicate whether the alcohol is primary, secondary, or tertiary. a. 1-butanol b. 2-butanol c. 2-methyl-1-butanol d. 2-methyl-2-butanol
Name all the alcohols that have the formula C5H12O. How many ethers have the formula C5H12O?
Name all the aldehydes and ketones that have the formula C5H10O.
Name the following compounds.a.b.
Draw the structural formula for each of the following. a. formaldehyde (methanal) b. 4-heptanone c. 3-chlorobutanal d. 5,5-dimethyl-2-hexanone
Draw a structural formula for each of the following. a. 3-methylpentanoic acid b. Ethyl methanoate c. Methyl benzoate d. 3-chloro-2,4-dimethylhexanoic acid
Draw’ the isomer(s) specified. There may be more than one possible isomer for each part. a. A cyclic compound that is an isomer of tows-2-burene b. An ester that is an isomer of propanoic acid c. A
Which of the following statements is (are) false? Explain why the starementfs) is (are) false.a.Is a structural isomer of pentonic acid. b. Is a structual isomer of 2-methyl-3-pentanone. c.
The following organic compounds cannot exist. Why? a. 2-chloro-2-butyne b. 2-methyl-2-propanone c. 1,1-dimethylbenzene d. 2-pentanal e. 3-hexanoic acid f. 5,5-dibromo-l-cyclobutanol
Mycomycin is a naturally occurring antibiotic produced by the fungus Nocardia acidophilus. The molecular formula of the substance is Q3H10O2, and its systematic name is
Distinguish between substitution and addition reactions. Give an example of each type.
Alkanes and aromatics are fairly stable compounds. To make them react, a special catalyst must be present. What catalyst must be present when reacting CI2 with an alkane or with benzene? Adding CI2
The following are some other organic reactions covered in Section 21.4. Give an example to illustrate each type of reaction. a. Adding H2O to an alkene (in the presence of H+) yields an alcohol. b.
In the presence of light, chlorine can substitute for one (or more) of the hydrogens in an alkane. For the following reactions, draw the possible monochlorination products.
Complete the following reactions.a.b. c. d.
Reagents such as HC1, HBr, and HOH (H2O) can add across carbon-carbon double and triple bonds, with H forming a bond to one of the carbon atoms in the multiple bond and Cl, Br, or OH forming a bond
Why is it preferable to produce chloroethane by the reaction of HCl(g) with ethene than by the reaction of Cl2(g) with ethane?
Give an example reaction that would yield the following products. Name the organic reactant and product in each reaction. a. Alkane b. Monohalogenated alkane c. Dihalogenated alkane d. Tetra ha
Using appropriate reactants, alcohols can be oxidized into aldehydes, ketones, and/or carboxylic acids. Primary alcohols can be oxidized into aldehydes, which can then be oxidized into carboxylic
Oxidation of an aldehyde yields a carboxylic acid:Draw the structures for the products of the following oxidation reactions. a. b. c.
Three different organic compounds have the formula C3H8O. Only two of these isomers react with KMnO4 (a strong oxidizing agent). What are the names of the products when these isomers react with
Give an example reaction that would yield the following products as major organic products. For oxidation reactions, just write oxidation over the arrow and don’t worry about the actual reagent. a.
How would you synthesize each of the following? a. 1,2-dibromopropane from propene b. Acetone (2-propanone) from an alcohol c. Terf-butyl alcohol (2-methyl-2-propanol) from an alkene d. Propanoic
What tests could you perform to distinguish between the following pairs of compounds?a.b. c. d. CH3CH2NH2, CH3OCH3
Complete the following reactions. a. CH3CO2H + CH3OH → b. CH3CH2CH2OH + HCOOH →
How would you synthesize the following esters?a. N-octylacerateb.
Define and give an example of each of the following. a. Addition polymer b. Condensation polymer c. Copolymer d. Homopolymer e. Polyester f. Polyamide
What is polystyrene? The following processes result in a stronger polystyrene polymer. Explain why in each case. a. Addition of catalyst to form syndioracric polystyrene b. Addition of 1,3-butadiene
Answer the following questions regarding the formation of polymers. a. What structural features must be present in a monomer in order to form a homopolymer polyester? b. What structural features must
What monomer(s) must be used to produce the following polymers?a.b. c. d. e. f. Classify these polymers as condensation or addition polymers. Which are copolymers?
Kel-F is a polymer with the structureWhat is the monomer for Kel-F?
The polymer nitrile is a copolymer made from acrylonitrile and butadiene; it is used to make automotive hoses and gaskets. Draw the structure of nitrile.
Polyararrud is a term applied ro polyamides containing aromatic groups. These polymers were originally made for use as tire cords but have since found many other uses.a. Kevlar is used in bulletproof
The polyester formed from lactic acid,Is used for tissue implants and surgical sutures that will dissolve in the body. Draw the structure of a portion of this polymer.
€œSuper glue€ contains methyl cyanoacrylate,which readily polymerizes on exposure ro traces of water or alcohols on the surfaces to be bonded together. The polymer provides a
Isoprene is the repeating unit in natural rubber. The structure of isoprene isa. Give a systematic name for isoprene. b. When isoprene is polymerized, two polymers of the form are possible. In
Polystyrene can be made more rigid by copolymerizing styrene with divinylbenzene,What purpose does the divinylbenzene serve? Why is the copolymer more rigid?
Polyimides are polymers that are tough and stable at temperatures up to 400°C. They are used as a protective coating on the quartz fibers in fiber optics. What monomers are used to make the
Polycarbonates are a class of thermoplastic polymers that are used in the plastic lenses of eyeglasses and in the shells of bicycle helmets. A polycarbonate is made from the re¬action of
In which polymer, polyethylene or polyvinyl chloride, would you expect to find rhe stronger intermolecular forces, assuming that the average chain lengths are equal?
When acrylic polymers are burned, toxic fumes are produced. For example, in many airplane fires, more passen deaths have been caused by breathing toxic fumes than by the fire itself. Using
Polyesters containing double bonds are often crosslinked by reacting the polymer with styrene. This type of reaction is common in the manufacture of fiberglass. a. Draw the structure of rhe copolymer
Another way of producing highly crosslinked polyesters is to use glycerol. Alkyd resins are a polymer of this type. The polymer forms very tough coatings when baked onto a surface and is used in
In Section 21.6 three important classes of biologically important natural polymers are discussed. What are the three classes, w’hat are the monomers used to form the polymers, and why are they
Give the general formula for an amino acid. Some amino acids are labeled hydrophilic and some are labeled hydrophobic. What do these terms refer to?
Distinguish between the primary, secondary, and tertian’ structures of a protein. Give examples of the types of forces that maintain each ty pe of structure.
Which of the amino acids in Fig. contain the following functional groups in their R group?a. Alcohol b. Carboxylic acid c. Amine d. Amide
Aspartame, the artificial sweetener marketed under the name NutraSweet, is a methyl ester of a dipeptide. The structure of aspartame is
Glutathione, a tripeptide found in virtually all cells, functions as a reducing agent. The structure of glutathione isWhat amino acids make up glutathione?
Draw the structures of the two dipeptides that can be formed from serine and alanine.
Write the sequence of all possible tetrapeptides composed of the following amino acids. a. Two phenylalanines and two glycines b. Two phenylalanines, glycine, and alanine
How many different pentapeptides can be formed using five different amino acids?
What types of interactions can occur betw’een the side chains of the following amino acids that would help maintain the tertiary structure of a protein? a. Cysteine and cysteine b. Glutamine and
Give examples of amino acids that could give rise to the interactions pictured in Fig. that maintain the ter-tiary structures of proteins.
Oxygen is carried from the lungs to tissues by the protein hemoglobin in red blood cells. Sickle cell anemia is a disease resulting from abnormal hemoglobin molecules in which a valine is substituted
Monosodium glutamate (MSG) is commonly used as a flavoring in foods. Draw’ the structure of MSG.
Over 100 different kinds of mutant hemoglobin molecules have been detected in humans. Unlike sickle cell anemia, not all of these mutations are as serious. In one nonlethal mutation, glutamine
Draw’ cyclic structures for D-ribose and D-mannose.
Indicate the chiral carbon atoms found in the monosac-charides D-ribose and D-mannose.
In addition to using numerical prefixes in the general names of sugars to indicate how many carbon atoms are present, we sometimes use the prefixes keto-and aldo-to indicate whether the sugar is a
What are the structural differences between α- and β-glucose? Each of these two cyclic forms of glucose is the building block to form two different polymers. Explain.
What is optical isomerism? What do you look for to de-termine whether an organic compound exhibits optical isomerism? 1-bromo-l-chloroethane is optically active, whereas l-bromo-2-chloroethane is not
Which of the amino acids in Fig. contain more than one chiral carbon atom? Draw the structures of these amino acids, and indicate all chiral carbon atoms.
Which of the noncyclic isomers of bromochloropropene is (are) optically active?
How many chiral carbon atoms does the following structure have?
Describe the structural differences between DNA and RNA. Describe the complementary base pairing between the two individual strands of DNA that forms the overall double-helical structure. How is
Which base will hydrogen-bond with uracil within an RNA molecule? Draw the structure of this base pair.
Tautomers are molecules that differ in the position of a hydrogen atom. A tautomeric fonn of thymine has the structureIf this tautomer, rather than the stable form of thymine, were present in a
The base sequences in mRNA that code for certain amino acids are Glu: GAA, GAG Val: GUU, GUC, GUA, GUG Met: AUG Trp: UGG Phe: UUU,UUC Asp: GAU, GAC These sequences are complementary to the sequences
The change of a single base in the DNA sequence for normal hemoglobin can encode for the abnormal hemo¬globin, giving rise to sickle cell anemia. Which base in the codon for glu in DNA is replaced
The average molar mass of one base pair of nucleotides in DNA is approximately 600 g/mol. The spacing between successive base pairs is about 0.34 nm, and a complete turn in the helical structure of
Is ocranoic acid more soluble in 1 M HC1, 1 M NaOH, or pure water? Explain. Drugs such as morphine are often treated with strong acids. The most commonly used form of morphine is morphine
Sorbic acid is used to prevent mold and fungus growth in some food products, especially cheeses. The systematic name for sorbic acid is 2,4-hexadienoic acid. Draw structures for the four geometric
When toluene reacts with chlorine gas in the presence of an iron(III) catalyst, the product is a mixture of the ortho and para isomers of C6H4ICH3. However, when the reaction is light-catalyzed with
Consider the reaction to produce the ester methyl acetate:When this reaction is carried our with CH3OH contain¬ing radioactive oxygen-18, the water produced does not contain oxygen-18. Explain
A compound containing only carbon and hydrogen is 85.63% C by mass. Reaction of this compound with H2O produces a secondary alcohol as the major product and a primary alcohol as the minor product. If
Poly(lauryl methacrylate) is used as an additive in motor oils to counter the loss of viscosity at high temperature. The structure isThe long hydrocarbon chain of poly(lauryl methacrylate) makes the
Ethelene oxide,is an important industrial chemical. Although most ethers are unreactive, ethylene oxide is quite reactive. It resembles C2H4 in its reactions in that many addition reactions occur
The Amoco Chemical Company has successfully raced a car with a plastic engine. Many of the engine parts, including piston skirts, connecting rods, and valve-train components, are made of a polymer
A urethane linkage occurs when an alcohol adds across the carbon€”nitrogen double bond in an isocyanate:Polyurethanes are formed from the copolymerization of a diol with a diisocyanate.
Stretch a rubber band while holding it gently to your lips. Then slowly let it relax while still in contact with your lips. a. What happens to the temperature of the rubber band on stretching? b. Is

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