Organic Chemistry - 5th Edition - by Janice Gorzynski Smith Dr. - ISBN 9780078021558
Buy this textbookBuy

Organic Chemistry
5th Edition
Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
ISBN: 9780078021558

Solutions for Organic Chemistry

Sample Solutions for this Textbook

We offer sample solutions for Organic Chemistry homework problems. See examples below:

All Bronsted-Lowry acids donate proton. Hydrogen bromide contain hydrogen atom. Hence, it is a...The given value of pKa is 7.0. The value of Ka is calculated by the formula, Ka=10−pKa Substitute...The given value of Ka is 4.7×10−10. The value of pKa is calculated by the formula, pKa = − log Ka...Reason for correct answer: (a) The deprotonation of an acid takes place in the presence of a strong...Draw the products of each reaction. Use the pKa table in Appendix A to decide if the equilibrium...The given ions are CH3C−H2, CH3O−, CH3N−H. Oxygen is more electronegative than nitrogen. The...In the given reaction, Lewis base H2O reacts with Lewis acid (CH3CH2)3C+ . Electron pair present on...The most acidic hydrogen in the compound esmolol is shown as, Figure 1 According to the structure of...The reaction of CH3CH2OH with H2SO4 is given as, Figure 1 The reaction of ethanol (CH3CH2OH) with...The given molecular formula is C4H8O. The double bond equivalent in the organic molecule is...The given compounds are (CH3)2C=CH2 and (CH3)2C=O. In (CH3)2C=CH2, C−C and C−H non polar bonds are...The given compound is, Figure 1 The functional groups present in Darvon are amine, ester and aryl...The given structure is, Figure 1 The given structure contains amine as a functional group. In the...The functional groups present in the given compound, quinapril are shown as, Figure 1 Thus, there...The functional groups present in the given compound, oxycodone are shown as, Figure 1 Thus, there...The given hydrocarbons of sex pheromone are saturated acyclic alkanes. The aliphatic hydrocarbons...Problem 4.7 Give the IUPAC name for each compound. a. b. c. d. The given compound is (CH3)3CCH2CH(CH2CH3)2. The skeletal structure of the given compound is, Figure...The given ball and stick model of alkane is, Figure 1 In ball-and-stick model, each colored ball...4.38 Give the IUPAC name for each compound. a. c. e. g. i. b. d. f. h. j. 4.40 Draw the structure corresponding to each IUPAC name. a. b. c. d. cyclobutylcycloheptane e....The given IUPAC name is 2,2−dimethyl−4−ethylheptane. The structure corresponding to the given IUPAC...The given bicyclic compound is shown below. Figure 1 The given compound contains seven carbon atoms...Cellulose is a polysaccharide with a molecular formula (C6H10O5)n. It is formed by the monomers of...The groups are prioritized on the basis of atomic number of their atoms. The group that contain atom...The given melting point of (S)-alanine is 297 °C. The (R)-alanine, and (S)-alanine are the...The priority can be assigned by numbering the groups which are bonded to the chiral carbon atom...The R or S configuration can be assigned by following CIP rules as follows. (1) Assign numbering to...The structure of given compoundis shown below. Figure 1 The stereochemistry of the compound is...The given Newman projection A is, Figure 1 In Newman projection, the circle represents the back...The specific rotation [α] of pure quinine is −165. [α] value for the solution is −50. The...Problem 6.1 Classify each transformation as substitution, elimination, or addition. a. c. b. d....Given The values of Keq are 1000 or 0.001. The value of ΔG° becomes negative if the value of...The given statement is “the reaction is faster than a reaction with Keq=8 and Ea=80 kJ/mol”. The...Given The value of Keq is 0.5. The given value of Keq is smaller than 1. It implies that the...Given The value of Keq is 23 when R=CH2CH3. The equilibrium reaction of monosubstituted cyclohexane...The mechanism of Equation [1] is shown below. Figure 1 The above reaction occurs in one step. The...Problem 7.1 Telfairine, a naturally occurring insecticide, and halomon, an antitumor agent, are two...The reactant of the reaction is (CH3)2CHCH2CH2Br. The structure of the product shows that SH group...The rate of SN2 reaction depends upon the concentration of reactant (alkyl halide, RX) and incoming...What happens to the rate of an SN1 reaction under each of the following conditions? a. [RX] is...The structure of the given alkyl halide shows that carbon atom, on which bromine is present, is...The structure of the given alkyl halide shows that carbon atom, on which bromine is present, is...The rate of SN1 reaction increases in the presence of good leaving group. Out of I− and Cl−, I− is a...The structure of the given alkyl halide shows that a carbon atom, on which bromine is present, is...Sodium hydride on reaction with HC≡CH leads to the formation of HC≡C−Na+. Acetylene lose one of its...Problem 8.1 Label the and carbons in each alkyl halide. Draw all possible elimination products...E2type of reaction is second order elimination reaction in which the rate of reaction depends on...The E2 elimination reaction involves the removal of halide and neighboring β hydrogen atom in the...For which reaction mechanisms, SN1, SN2, E1 or E2-are each of the following statements true? A...Draw the organic products formed in each reaction. a. d. g. b. e. h. c. f. Draw all products, including stereoisomers, in each reaction. a. c. b. d. The reaction of dibromide A with one equivalent of NaNH2 results in the elimination of one mole of...Problem 9.1 Label each ether and alcohol in brevenal, a marine natural product. Classify each...The given reagent is SOCl2, pyridine. Alkyl chlorides are obtained by the reaction of 1ο or 2ο...Answer each question using the ball-and-stick model of compound A. a. Give the IUPAC name for A,...The given structure of alcohol is in the form of ball-and-stick model. It is converted into skeletal...The name of the given compound is trans-2-methylcyclohexanol. The root name cyclohexanol suggests...9.45 Draw the organic product(s) formed when is treated with each reagent. The given reagent is HBr. Hydrogen bromide (HBr) is a strong acid. The opening of an...The given reaction involves treatment of unsymmetrical epoxide with CH3CH2OH; H2SO4, an acid. The...The given reaction involves treatment of alkyl tosylate with KOC(CH3)3, a strong nucleophilic base....The given molecular formula of the compound is C5H10. The first possible structure of alkene with...The given molecular formula is C6H6. The number of carbon and hydrogen atoms present in C6H6 are six...The compounds with same chemical formula but different arrangement of atoms in space are known as...The given molecular formula is C6H8. The number of carbon and hydrogen atoms present in C6H8 are six...The given compound is, Figure 1 The numbering of carbon atoms present in the longest carbon chain is...The given IUPAC name is (E)−4−ethylhept−3−ene. Rules for writing structural formula from IUPAC are...A reaction of hydrogen halide with alkene results in the formation of alkyl halide. This type of...For preparation of alkenes, acid-catalyzed dehydration of alcohols is one of the best methods. Less...Problem 11.1 Neopheliosyne B is a novel acetylenic fatty acid isolated from a New Caledonian marine...The reaction of CH3CH2C≡C−Na+ with CH3CH2CH2Br is shown as, Figure 1 Thus, the product that is...The structure corresponding to the given name, 5,6−dimethylhept−2−yne is shown as, Figure 1 This...The reaction of hex−1−yne with HCl(2 equiv) is shown as, Figure 1 The reaction of hex−1−yne with...The reagents that are needed to convert (CH3CH2)3CC≡CH into the given compound are shown as, Figure...The alkynes that forms the given ketone as the only product after hydration with H2O, H2SO4 (strong...The reaction of hept−1−yne with two equivalents of HBr is shown as, Figure 1 The reaction of...The given reaction is, Figure 1 There is decrease in the number of C−O bonds. Hence, this is a...For compound A: Before hydrogenation, the molecular formula is C10H12. The maximum number of H's...The given molecule is, Figure 1 The red coloured balls have two bonds. So, these are the oxygen...For compound A: Before hydrogenation, the molecular formula is C5H8. The maximum number of H's...In the given reaction, when cyclopentene is treated with H2+Pd-C, the C−C double bond is reduced to...When A is treated with H2+Pd-C, the C−C double bond is reduced to C−C single bond. The product...[1] OsO4 followed by NaHSO3+H2O In presence of OsO4 followed by hydrolysis with NaHSO3+H2O, 1,2-diol...Synthesis of the given compound is shown below. Figure 1 In the first step acetylene is converted to...The molecular weight of compound is equal to the mass of the molecular ion. The molecular weight and...The molecular formula of the compound is C4H9Cl. Chlorine atom has two isotopes 35Cl and 37Cl. The...The given compound is octane. It contains Csp3−H and Csp3−Csp3 bonds. Hence, the major IR absorption...The molecular formula of given compound is C6H6. The m/z value of C6H6 is calculated as, Mass of...The molecular ion peak of a given compound is observed at m/z=102. Possible hydrocarbons are...The molecular ion peak of a compound is observed at m/z=107. Possible hydrocarbons are calculated...The given compound is ethynylcyclohexane as shown below. Figure 1 It contains Csp-H and Csp≡Csp...Problem 14.1 The NMR spectrum of recorded on a NMR spectrometer consists of two signals, one...The number of signals in each compound is equal to the number of hydrogen atoms present in a...The number of signals in each compound is equal to the number of hydrogen atoms present in a...The given compound is (CH3)2−CH−CO2CH3. The labeled proton is bonded to a carbon atom that has two...The given compound is ethyl methyl ether (CH3−O−CH2CH3). It contains three types of proton Ha, Hb...In the given compound, one carbon atom is bonded to three other carbon atoms on which three hydrogen...In NMR spectroscopy, splitting of signal takes place according to number of protons present on...In 13C NMR, the number of signals depends upon the chemical environment of each carbon atom. Same...The given species is, Figure 1 The given free radical is attached to two carbon atoms. Thus, it is...The given species is, Figure 1 Three types of radicals can be formed by the cleavage of C−H bond in...The given species is, Figure 1 Three types of radicals can be formed from cleavage of C−H bond in...The reaction of alkene with N−bromosuccinimide in presence of light results in the formation of...Electrophilic addition reaction follows Markovnikov rule. According to Markovnikov rule, the...The energy required to break the 1∘ C−H bond is more than the energy required to break the 2∘ C−H...The given bromination reaction is, (CH3)3CH+Br2→Δ(CH3)3CBr+HBr In the given reaction, Br−Br and C−H...Cyclopentane is used as a starting material and it converts into bromocyclopentane on treatment with...Diene is a hydrocarbon that contains two C=C double bonds in a compound. Conjugated diene consists...The given species is shown below. Figure 1 Delocalization of electrons from one position to the...The given name is (2E,4E)−octa−2,4−diene. The word root used in this is oct. It means structure...The given structure of NPD1 is shown below. Figure 2 Diene is a hydrocarbon that contains two C=C...Conjugated dienes undergoes electrophilic addition to gives a mixture of products that is...The method by which overall delocalization of electrons can be described in a particular molecule is...The given name is (Z)−penta−1,3−diene. The word root used in this is pent. It means structure...Conjugated dienes undergoes electrophilic addition to gives a mixture of products that is...The given structure of antihistamine diphenhydramine is shown below. Figure 1 The given structure...The IUPAC name of the compound is isobutyl benzene. The parent ring is benzene. 2-methylpropyl is...The given compound is, Figure 1 The parent ring is benzene. The substituent attached to the benzene...The IUPAC name of the compound is p-dichlorobenzene. The parent chain consists of benzene ring. Two...The 13C NMR spectroscopy is an important tool for the elucidation of organic structures of...The given set of IR data is, C10H14: IR absorptions at 3150−2850, 1600, and 1500 cm−1 Information...The given sets of IR and 1H NMR data for Compound A are, Molecular formula: C8H10OIR absorptions at...Benzene is an aromatic compound. A non-aromatic compound is formed by the addition reaction of...Electron withdrawing groups deactivates the ring towards the electrophilic substitution reaction....The Friedel-craft alkylation of aromatic compound with CH3Cl in presence of AlCl3 involves...The aromatic compound on reaction with HNO3 in presence of H2SO4 undergoes nitration reaction. The...An aromatic compound undergoes nitration on reaction with HNO3 in the presence of H2SO4. The OH...The inductive effect appears in a molecule due to the difference in electron negativity of atoms....The electron donating groups or activating groups make benzene ring more electron rich, as a result...The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in...The numbering of carbon atoms in the given compound is shown below. Figure 1 The given compound has...The structure of alcohol that can be oxidized to the given carboxylic acid is shown below. Figure 1...The structure of the given compound is shown below. Figure 1 The above compound has a chain of eight...The name of the compound is 3,3−dimethylpentanoic acid. The name suggests that the longest carbon...The given carboxylic acid is 4-methyl benzoic acid. Its pKa value is 4.3. It is less acidic because...The given compound is FCH2COOH. Fluorine is electron withdrawing group due to which its acidic...The given compound is, Figure 2 The conjugate base formed by the removal of Hc is shown below....19.57 Identify each compound from its spectral data. The given structure of α- sinensal is, Figure 1 Bond [1] is formed by the overlapping of sp2 hybrid...The reduction of ketone by LiAlH4, then H2O yields secondary alcohol. The double bond is not reduced...The given compound is, Figure 1 The product formed by the reaction of given compound with two...The given compound is aldehyde. Acid chlorides on reaction with mild reducing agent like lithium...The given reagents are organocuprate ((CH3)2CuLi) and organolithium (HC≡CLi). Organocuprate reagent...The ball and stick model of compound A and B shows that black balls represent carbon atom, white...The reaction that shows the formation of product when pentanal reacts with NaBH4, CH3OH is shown...Acid chlorides on reaction with organocuprate convert into ketone. The alkyl group of organocuprate...The reaction that shows the formation of product when α,β− unsaturated ketone reacts with NaBH4,...Rank the following compounds in order of increasing reactivity towards nucleophilic attack. The IUPAC name of the given compound is 2-isobutyl-3-isopropylhexanal. One should follow the given...The given name is sec-butyl ethyl ketone. One should follow the given two steps to derive the...The given compound is benzene. The conversion of benzene into acetophenone involves acylation of...The stereogenic centers in α-D-galactose are shown below. Figure 1 The stereogenic centers are...21.43 Give the IUPAC name for each compound. a. c. e. b. d. f. The given name is 2−methyl−3−phenylbutanal. The word root used in this is but. It means structure...21.46 Draw the products of each reaction. a. e. b. f. c. g. d. h. Structure determination of Compound A: The molecular formula of the Compound A is C5H10O....The classification of each amide group present in oxytocin as 1o, 2o, or 3o is shown as, Figure 1...The given name indicates that compound contains acid chloride (name ends with –yl chloride) as the...The given treatment involves reaction of benzoic anhydride [(C6H5CO)2O] with H2O. Anhydrides involve...Grignard reagents converts nitriles to corresponding carbonyl groups. CH3MgCl can be used to convert...The given compound A is, Figure 1 The red coloured ball has two bonds. So, this is the oxygen atom....The given name indicates that compound contains ester (name ends with –ate) as the functional group,...Carboxylic acids react with NaHCO3 to form sodium salts of carboxylic acid. Phenylacetic acid...The given compound is a nitrile. Hydrolysis of nitriles in acidic medium converts them to the...The IR absorption value of the given compound is 1738 cm−1 which corresponds to that of an ester....The enol or keto tautomer of the given compound is shown as, Figure 1 The keto form of the given...The product that is formed by the reaction of the given starting material with LDA in THF solution...The enolate that is formed by the reaction of the given ketone with LDA present in the THF solution...The product that is formed by the reaction of 2−bromopentan−3−one with Li2O3, LiBr, DMF is shown as,...The product that is formed by the reaction of the given compound with LDA in the presence of THF...The given carboxylic acid is, Figure 1 All alkyl groups on the alpha carbon will be obtained from...The given compound is, Figure 1 The nucleophile −CH(CO2Et)2 attacks on the electrophilic centre of...Decarboxylation occurs when a carboxyl group is attached to alpha carbon of another carbonyl group....The aldol product that formed by the given compound is shown below. Figure 1 In this aldol reaction,...The product that is formed in the given crossed aldol reaction is shown below. Figure 1 In this...The aldol product that is formed by the reaction of the two molecules of butanal in the presence of...The product that is formed by the Robinson annulation reaction of the given pair of compounds with...The product that is formed by the Robinson annulation reaction from the given starting materials by...The lettered reagent A is shown as, Figure 1 The given compound, cyclopentanone is treated with the...The given compound is, Figure 2 The starting materials needed to form 2-acetylcyclopentanone by a...The stereogenic centers in the given compound are shown below. Figure 1 The highlighted nitrogen...The IUPAC name of the compound is 2, 4-dimethylhexan-3-amine. The parent chain consists of hexane...Amines on reaction with acid chlorides and anhydride form corresponding amide whereas on reaction...Primary and secondary amines on reaction with NaNO2 in the presence of HCl yield different products....The name of the given molecule suggests that a nitrogen atom is bonded to cyclopentane and isobutyl...The product formed by the treatment of p- methylaniline with HCl is shown below. Figure 1 In the...The products formed when the given amine reacts with [1] CH3I(excess); [2] Ag2O are shown below....The reaction between (2-chloroethyl) cyclohexane and excess ammonia is shown below. Figure 2 In the...Species containing copper-carbon bonds are known as organocuprate reagents. These reagents act as...26.20 Draw the products formed in each reaction. c. d. e. g. f. h. 26.34 Draw the products formed in each reaction. a. e. b. f. c. g. d. h. The treatment of an organic halide (R'X) with an organoborane reagent (RBY2) in the presence of Pd...The given compound is a diene. The ring-closing metathesis (RCM) by Grubbs catalyst occurs, when the...The given compound is a diene. The ring-closing metathesis (RCM) by Grubbs catalyst occurs, when the...The given reaction is shown below. Figure 1 The sigma bond that is broken during the conversion of...The molecular formula of deca −1,3,5,7,9− pentaene is CH2=CH−CH=CH−CH=CH−CH=CH2−CH=CH2. The formula...The thermal electrocyclic ring closure reaction is shown below. Figure 1 Electrocyclic reactions...The given product is shown below. Figure 1 Retro synthesis can be carried out to identify the diene...The product of the [3,3] sigmatropic rearrangement for the given compound is shown below. [a1]...The given reaction is shown below. Figure 1 The product formed for the given reaction is shown...The name ketotetrose suggests that it is a monosaccharide that contains four carbon atoms and a...The OH groups of monosaccharides on reaction with base and an alkyl halide convert into ether. A...The structure of compound A is, Figure 1 In the compound A, CHO, OH, CH2CH3 and H substituents are...The structure of given compound is, Figure 1 The horizontal and vertical line represents the bonds...The structures of compounds and are, Figure 1 In the given structures, the configuration at is...The conversion of hydroxyl groups of α- D-gulose into the ether groups in presence of base and...The OH groups of monosaccharides on reaction with alcohol in the presence of strong acid result in...The structure of stachyose, Figure 1 The acetals containing alkoxy groups attached to anomeric...The structure of l-isoleucine is, Figure 1 L-leucine has two stereogenic centers. Maximum number of...In the given ball-and-stick model of amino acid, the black balls represent carbon atoms, the white...At isoelectric point, the amino acids exist in their neutral form. The amine groups exists as −N+H3...At isoelectric point, the amino acids exist in their neutral form. The amine groups exists as −N+H3...In the given reaction, the oxygen of carboxyl group takes a proton from an acid. The carbon of...The monomer required for the formation of poly (vinyl chloride) is vinyl chloride. A shorthand...The given pair of polymers is, Figure 1 The above polymer chains have both crystalline regions and...The given substituted styrene resembles to CH2=CHZ alkene, where Z=C6H4OCH3. This means benzene ring...The given alkene undergoes radical polymerization in presence of peroxide to form the polymer. The...Waxes are lipids, which are hydrolysable. They contain ester (RCOOR') as the functional group, and...Terpenes are composed of repeating five-carbon units. These units are called isoprene units. Figure...The structure of isoprene is, Figure 2 The isoprene unit contains four carbon atoms in the long...The structure of isoprene is, Figure 1 The isoprene unit contains four carbon atoms in the long...In presence of base and acetyl chloride, the hydroxyl group of cholesterol undergoes acetylation....In presence of base and acetyl chloride, the hydroxyl group of cholesterol undergoes acetylation....

More Editions of This Book

Corresponding editions of this textbook are also available below:

Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Organic Chemistry
4th Edition
ISBN: 9780073402772
ORGANIC CHEM W/BIOLOGICAL TOP. ACCESS
6th Edition
ISBN: 9781264382545
ORGANIC CHEMISTRY W/BIOLOGICAL TOPICS
6th Edition
ISBN: 9781260325294
ORGANIC CHEMISTRY-ACCESS
6th Edition
ISBN: 9781260475586
Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Study Guide/solutions Manual For Organic Chemistry
6th Edition
ISBN: 9781260475678
ORGANIC CHEMISTRY (LOOSELEAF)
6th Edition
ISBN: 9781260475630
CNCT ORG CHEM 6 2020
6th Edition
ISBN: 9781266807244
LL ORG CHEM
6th Edition
ISBN: 9781264840083
ORG CHEM CONNECT CARD
6th Edition
ISBN: 9781264860746
ORGANIC CHEMISTRY
6th Edition
ISBN: 9781266633973
EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 9781260475685
ORGANIC CHEMISTRY
6th Edition
ISBN: 9781260826791
ORGANIC CHEMISTRY BOOK& SG/SM
6th Edition
ISBN: 9781264094493
ORGANIC CHEMISTRY W/ALEKS
6th Edition
ISBN: 9781264905430
ORGANIC CHEMISTRY - LOOSELEAF W/CONNECT
6th Edition
ISBN: 9781266060144
ORGANIC CHEMISTRY W/CONNECT & ALEKS
6th Edition
ISBN: 9781264683888
Connect Online Access 1-Semester for Organic Chemistry
6th Edition
ISBN: 9781260475609
Organic Chemistry
3rd Edition
ISBN: 9780077354725
PKG ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259963667
Package: Loose Leaf for Organic Chemistry with Biological Topics with Connect Access Card
5th Edition
ISBN: 9781260170405
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596

Related Chemistry Textbooks with Solutions

Still sussing out bartleby
Check out a sample textbook solution.
See a sample solution