Organic Chemistry: Principles and Mecha...2nd EditionJoel Karty Publisher: W. W. Norton & CompanyISBN: 9780393663556
Organic Chemistry: Principles and Mecha...
Solutions for Organic Chemistry: Principles and Mechanisms (Second Edition)
Browse All Chapters of This Textbook
Chapter 1 - Atomic And Molecular StructureChapter A - Nomenclature: The Basic System For Naming Organic CompoundsChapter 2 - Three-dimensional Geometry, Intermolecular Interactions, And
physical PropertiesChapter 3 - Orbital Interactions 1: Hybridization And Two-center Molecular OrbitalsChapter B - Naming Alkenes, Alkynes, And Benzene DerivativesChapter 4 - Isomerism 1: Conformers And Constitutional IsomersChapter 5 - Isomerism 2: Chirality, Enantiomers, And DiastereomersChapter C - Stereochemistry In Nomenclature R And S ConfigurationsChapter 6 - The Proton Transfer Reaction: An Introduction To Mechanisms, Thermodynamics, And Charge StabilityChapter 7 - An Overview Of The Most Common Elementary Steps
Chapter D - Molecular Orbital Theory, Hyperconjugation, And Chemical ReactionsChapter E - Naming Compounds With A Functional Group That Calls For A Suffix 1Chapter 8 - An Introduction To Multistep MechanismsChapter 9 - Nucleophilic Substitution And Elimination Reactions 1Chapter F - Naming Compounds With A Functional Group That Calls For A Suffix 2Chapter 10 - Nucleophilic Substitution And Elimination Reactions 2Chapter 11 - Electrophilic Addition To Nonpolar π Bonds 1Chapter 12 - Electrophilic Addition To Nonpolar π Bonds 2Chapter 13 - Organic Synthesis 1: Beginning Concepts In Designing Multistep SynthesisChapter 14 - Orbital Interactions 2: Extended π Systems, Conjugation, And AromaticityChapter 15 - Structure Determination 1: Ultrabiolet-visible And Infrared SpectroscopiesChapter 16 - Structure Determination 2: Nuclear Magnetic Resonance Spectroscopy And Mass SpectroscopyChapter 17 - Nucleophilic Addition To Polar π Bonds 1Chapter 18 - Nucleophilic Addition To Polar π Bonds 2Chapter 19 - Organic Synthesis 2: Intermediate Topics In Synthesis Design, And Useful Redox And Carbon-carbon Bond-forming ReactionsChapter 20 - Nucleophilic Addition–elimination Reactions 1: The General Mechanism Involving Strong NucleophilesChapter 21 - Nucleophilic Addition–elimination Reactions 2: Weak NucleophilesChapter 22 - Aromatic Substitution 1: Electrophilic Aromatic Substitution On Benzene; Useful Accompanying ReactionsChapter 23 - Aromatic Substitution 2: Reactionsof Substituted Benzenes And Other RingsChapter 24 - The Diels–alder Reaction And Other Pericyclic ReactionsChapter 25 - Reactions Involving Free RadicalsChapter G - Fragmentation Pathways In Mass SpectrometryChapter 26 - Polymers
Sample Solutions for this Textbook
We offer sample solutions for Organic Chemistry: Principles and Mechanisms (Second Edition) homework problems. See examples below:
The atomic number of carbon is six. There are six protons in its nucleus. The neutral carbon atom...The given species is: The formula for the species above is C2H5NO. The total number of valence...The atomic number of Aluminum is 13. These 13 electrons need to be distributed in atomic orbitals....The given molecule CH5N has 14 valence electron in total, with carbon as the central atom bonded to...The given structure is Total valence electron count for the given molecule is 54 valence electrons....The total of valence electrons based on the formula C2H5 anion is 2(4) + 1(5) + 1 = 14. Based on the...The given Lewis structure is: In the given Lewis structure, there are two CH2 units in the middle....The given line structure is: In the given line structure, there is a five carbon chain, with a...The given line structure is: In the given line structure, there is a five carbon chain, with a...
The structures of the given pair are shown below: The two structures have completely different...The given molecule is: In this molecule, there are two carbon atoms in the straight chain. Hence,...The given structure is In the structure above, the ring has more carbon atoms than any of the...The given IUPAC name is 2, 4-dicyclopropyl-2-ethoxyhexane. The root name ‘hexane’ indicates the...The given molecule is: In this molecule, the six carbons ring act as a parent. Hence, the root is...The given molecule is In this molecule, the longest continuous chain of carbon atoms has five carbon...The given acetone imine molecule is In acetone imine molecule, there are total three groups of...The given structure for prop-2-yn-1-ol is: The structure showing all the atoms and lone pairs is:...(A) The functional groups from the given table which possess at least one H- bond acceptor but no H-...The Lewis structure is drawn based on the total valence electrons in the structure. Carbon atom has...The Lewis structure is drawn based on the total valence electrons in the structure. Carbon atom has...The given molecular ion is: In this molecular ion, the charged atom is nitrogen. Nitrogen has two...The given ball-stick model and the line structure are: In the given ball-stick model, the yellow...The electrostatic potential map shows the molecule with a negative charge concentrated at the...The given molecule is in trans form. The directions of the vectors of both the C-F bonds are equal...The methyl cation is CH3+. It is a positively charged ion and thus, it can be attracted to the...The orbital interaction shows two orbitals that are lightly shaded. Both have the same negative...The line drawing of the given molecule is: This must be converted to a Lewis structure showing all...The structure of the molecules mentioned in the question is shown below: The two sp hybrid atomic...The Lewis structure is drawn based on the total valence electrons in the structure. The carbon atom...The Lewis structure of levomenol is drawn based on the total valence electrons in the structure. The...The structure of Norethynodrel is as below: The nonhydrogen atoms are highlighted with red color and...The given structure for Octocrylene is: The above molecule has two benzene rings. Each carbon atom...The given molecule is In this molecule, the largest ring containing the double bond has six carbon...The given molecule is: In this molecule, the largest carbon ring containing the double bond has six...The given molecule is 2-chloropropene In this molecule, the root is propene. Thus, the longest...The given molecule is: In this molecule, the longest carbon chain containing the double bond has...The given molecule is In the given molecule, the longest carbon chain containing all C=C groups has...The given Newman projection is: In this Newman projection, the front carbon atom is shown by a...The structures of the given molecules are The molecular formula of the first compound is C6H10, and...Aldotetrose is a mono-saccharide. The name “aldo” indicates that the carbonyl group must be present...The dash-wedge structure of the molecule is: The dash-wedge structure shows one hydrogen atom, two...The given compound is: The cyclohexane ring has two methyl groups attached. Both these methyl groups...The given compound is The cyclohexane ring has two substituents attached. One of them is tertiary...The given compound is This compound has all single bonds and is a saturated compound. There are no...The given molecular formula is C6H6. The general formula of a saturated hydrocarbon is CnH2n+2,...The two structures in the given pair are Both the above structures contain the largest carbon ring...The given molecule is: In the given molecule, there is a six member cyclic structure containing...Molecules in the given pair are In the above pair, both molecules have carbon as the central atom...The given original enantiomer is: The molecule which is to be compared is: The given molecule is the...The structure of the given molecule is A chiral center must be an sp3 hybridized atom bonded to four...The structure of the given molecule is A chiral center must be an sp3 hybridized atom bonded to four...Structure of the given molecule is: Expanding this line drawing to show the terminal carbons and...The given molecule is The given molecule consists of a five carbon chain, each of which is numbered....The given pair of compounds is Both the molecules in the given pair have the same molecular formula;...Structures of the two molecules are: Both molecules contain the same number of carbon atoms....The Fischer projections are After converting the Fischer projections to dash-wedge representation,...The given pair of atoms is: F and O. The atomic number of fluorine is 9 while that of oxygen is 8....The given molecule is The IUPAC name for the above molecule, without considering the...The given name is: (R)-1-chloro-1-fluorobutane In this compound, the root is butane. The longest...The given name is: (R)-3-chloropent-1-ene In this compound, the root is pentene. The compound...The given proton transfer reaction is between ammonia (NH3) and water, where water acts as the acid...The reaction of HC≡C:Θ with water is shown below: Water, H2O (pKa = 15.7), is a stronger acid than...The curved arrow notation for the given proton transfer reaction is shown below: In a proton...The given proton transfer reaction is In the above reaction, the bond (C-H) is formed between the C...The initial concentration of phenol is calculated as [C6H5OH] = moles of phenolsolution volume (L) =...The given reaction is: The ion HO− is the strongest base that can exist. It deprotonates the amide...The general reaction between acid, HA, with water is HA + H2O ⇌ A- (aq) + H3O+ (aq) The pH of the...The reaction of ΘNH2 with ethanol is shown below: Ethanol, CH3CH2OH (pKa = 16), is a stronger acid...The reaction of chloride ion ClΘ with ethanamine is shown below: Hydrochloric acid, HCl (pKa = -7),...The structure for the given compound is: There are three protons that could be acidic. The proton...The given pair of species is The second species has negative charge whereas the first species is...Atoms in CH3OH do not bear full charge. However, the high electronegativity of oxygen leads to a...In the given nucleophilic addition step is: In this step, CH3OK is treated as CH3O- which acts as a...Product for the given nucleophilic addition step is: In the given product, there are two possible...The given substrate is E2 or bimolecular elimination step can take place when a strong base is in...The structure of the carbocation is The charge is on the carbon numbered 1. There are two hydrogen...The given elementary step is The given elementary step is for an SN2 reaction. In the above...The first elementary step is: In this step, the carbonyl oxygen of benzoic acid having lone pairs is...The first elementary step is: In the given elementary step, on the reactant side the oxygen atom...In CF3CH2+ ion, the filled σ bonding orbital is of the adjacent C-F bond of CF3 which can interact...In (CH3)2CHC+HCH3, the four carbon atoms are sp3 hybridized, and the positively charged carbon is...The given compound is In this compound, the functional group is alcohol. The parent is a four carbon...The name for the given molecule is divinyl ketone. The vinyl in the trivial name indicates the...The given molecule is: The molecule above contains two OH functional groups. Thus, a prefix ‘di’ is...The given compound is: In this compound, the highest priority functional group is ketone, thus, the...The given IUPAC name is (2S, 3R, 4R)-2, 3-diamino-4-hydroxycyclopentanone. The root name in this...The given reaction is The given substrate is a secondary alkyl halide. Chlorine is a moderately good...The given reaction is: The reactant molecule contains one chiral center at the C2 carbon atom. The...(i) The given reaction is In the above reaction, NaOH acts as OH- (nucleophile). In SN2 reaction,...The given reaction equation is: E2 reaction: In the given reaction, NaOH is a base. The substrate...The given substrate initially forms the carbocation shown below in an SN1 or E1 mechanism. It is a...The given reaction equation is Here, the chlorine atom is the leaving group, which can be eliminated...The given reaction equation is In first step, the leaving group Br detaches from the carbon and...In the case of an SN2 mechanism, the nucleophile attacks the reactant, and at the same time, the...(i) The first given pair of nucleophiles is CH3O− and CH3CO2−. The reactions of each of these...Both SN2 and E2 reaction rates depend on the concentration of the attacking species. In an SN2 and...Acetone is an aprotic solvent and will not have a significant effect on the strength of the...The given pair of nucleophiles is CH3−OH and CH3−O−. Negatively charged nucleophiles are stronger...The given reaction is The structure of (S)−3−chlorooctane is The substrate has one site for...The given reaction is The absolute configuration of the substrate is S. This is solvolysis reaction...Elimination usually takes place so as to produce the most stable, i.e., highly alkyl substituted,...The given reaction is: It is mentioned that the reaction would follow the SN1 mechanism pathway. The...The given reacting species are shown below: In the given reaction, attacking species is an alcohol...The structure of L-asparagine is The highest priority function group in L- asparagine is carboxylic...The compound is a carboxylic acid, with the carboxyl functional group attached to a five-membered...The given IUPAC name is trichloroacetic acid. The name suggests that it is a monocarboxylic...The given trivial name is acrylonitrile. The given name indicates that the high priority functional...The given reaction is as follows: The hydroxyl (-OH) group in the given substrate is a leaving group...The given reaction is: Deuterium is an isotope of hydrogen. Its chemical behavior is identical to...The structure of the given ether is In this ether, one of the R groups is a phenyl ring, and the...The given reaction is: When the given epoxide is treated with sodium azide (basic conditions), the...The given reaction is The given reaction occurs in two steps. The electrophilic addition is the...The structure of the given bromoalkane is In the structure above, the carbon atom to which the...The given addition reaction is Water is a weak acid and does not add to the alkene in neutral...The structure for the given compound 4-chloro-1, 2-dimethylcyclohexane is The compound shown above...The structure for the given compound pentan-2-ol is To form the given alcohol by electrophilic...The structure for the given compound (1, 1-Dichloro-2-cyclopentylethyl)benzene is: The given...The given reaction is 4-Chlorobut-1-ene + HBr → ? The substrate is an alkene, and the other reactant...The given reaction is In the first step of the reaction mechanism, the CH2N2 bond breaks...The given compound is: Electrophilic addition of carbenes to alkenes forms cyclopropane rings....Diazomethane dissociates heterolytically when irradiated with ultraviolet light to produce a carbene...The starting material for the given reaction is When alkene is treated with molecular bromine (Br2)...The given reaction is Cyclopentylethene, a terminal alkene, in presence of H3O+ undergoes an acid...The given equation is In the substrate, the alkene C=C bond is terminal, and the product has OH...The given reaction is The structure of cyclopentylethene is In the first step, borane adds across...The structure of the given compound is Alcohol with a specific stereochemistry is to be synthesized...The reaction sequence given in Your Turn 13.6 is: The first reaction is the conversion of an epoxide...The given proposed transform is: The target molecule is on the left side. In the target molecule,...The given synthesis scheme is: In the given synthetic route, the reactant having functional group...The given chemical synthesis is The starting compound is a six carbons ring whereas the product is a...The given synthetic reaction is In the given synthesis, the product differs from the starting...The given proposed synthetic step is: The reactant molecule has a good leaving group, -OTs. The...The structure of the desired alkene is: The given alkene has both the higher priority groups...All three carbon atoms in the allyl anion are sp2 hybridized. Each atom has one pure p AO, with all...The structure of the given molecule is In the given compound, six carbon atoms are sp2 hybridized,...The given compound is: It is a heterocyclic compound with an oxygen atom. The hybridization of the...The phases of the wave function of the two AOs on either side of a nodal plane are opposite each...The phases of the wave function of the two AOs on either side of a nodal plane are opposite each...The bond length of C - C single bond in hexa-1, 3, 5-triene is 146 pm is shown below: The normal C -...The given line structure of the cyclic ion is: The given ion is trigonal and has three vertices with...The given structure is: The molecule has total 14π electrons, out of which 12π electrons could form...It is given that the intensity of the radiation from the source (Isource) is 1.0 × 10-4 W and the...The given pair of compounds is, The triple bonds tend to be stronger and stiffer than double bonds....The given molecular formula is C5H6. A completely saturated molecule with 5C would have 12H, but the...The given reaction is: In the above reaction, both the reactant and product have two double bonds;...The given reaction is In the above reaction, the OH group, that is the alcohol functional group, is...The given molecule is The given molecule has a ketone and alcohol as functional groups. According to...The compounds from Table 15-1 that contain only C and H, the number of conjugated double bonds in...The difference in energy between the two spin states of a proton is given by the equation: ΔEspin =...The given molecule is: There are five H atoms in the above compound. These H atoms are not easily...The structure of the given compound is The compound has three chemically distinct protons indicated...The given proton NMR for the unknown 1 in Figure 16-32 is The given molecular formula for unknown 1...The molecular formula for the given unknown compound is C9H10O2. The molecular formula shows an...The structure of the given compound is The given compound has a plane of symmetry and thus has two...The structure of the molecule with the specific H highlighted is The signal for that H can be split...The structure of the given molecule is The molecule has a plane of symmetry, which divides the...The given compound is There are two types of chemically different H atoms and three types of C atoms...The molecular formula for the given unknown compound is C19H16. The molecular formula shows an index...The formula of the compound is C9H10O3. The IHD for this compound is IHD = (CnH2n+2 - CnHx)/2=...The formula of the compound is C4H10O2. The IHD for this compound is IHD = (CnH2n+2 - CnHx)/2=...The given reaction is Alcohols undergo a substitution reaction when treated with a strong Bronsted...The given reaction is: KCN is ionic, so it dissolves in water as K+ and CN- ions. CN- has a...The nucleophile CH3S- is less reactive and adds reversibly to the cyclohex-2-en-1-one. The...The given pair of compounds are The electron-donating groups attached to the carbonyl carbon will...The given reaction is LiAlH4 is the source of H- ion; this reagent is used to reduce a ketone to a...The given reaction is In the given reaction, the starting material is a cyclic ketone, and the...The given alkyl halide is The Wittig reagent is generated from the given alkyl halide and...The given structure of alkene is In the above structure, the C=C is formed via a Wittig reaction....The weak resonance contributor with separated charges generates a small partial positive charge on...The given reaction is, The first step of the reaction is reduction of α,β- unsaturated carbonyl to...The given starting material and reagents are as shown below: The reagent used for the first step of...The given reaction is: Under neutral conditions, water acts as the nucleophile. The electrophilic...Even though NC- is a charged nucleophile, it adds to an α,β-unsaturated carbonyl reversibly....The first given reaction is Under the basic condition, the base (HO-) deprotonates the nucleophile...The given reaction is This is an acetal formation reaction in which the reaction is catalyzed by...The given reaction is This is an acetal formation reaction in which the reaction is catalyzed by an...The given reaction is This is an imine formation reaction in which the reaction is catalyzed under...The given reaction is This is an acetal hydrolysis reaction under strongly acidic conditions to...The given reaction is as shown below: The given reaction is aldol condensation as the sodium...The given reaction is as shown below: The given reaction is a crossed aldol condensation as the...The given compound is: The given compound is a α,β- unsaturated ketone, the double bond between α...The given molecule is α-D-allopyranose. The structure of α-D-allopyranose can be drawn from the...IHD of C5H8O is 2 and for C10H14O it is 4. Comparing the formulas C5H8O and C10H14O we can observe...The given reaction is Magnesium is an active metal and reacts with the polar C−I bond. It extracts...The given Grignard reagent is: The given Grignard reagent can be prepared from alkynyl bromide as...The given reaction is, In the above reaction, the C atom of the C-Br bond is electron-poor. When the...The given reaction is The given reaction condition correlates to catalytic hydrogenation; it reduces...The given reaction is This is an example of an oxidation of a primary alcohol using sodium...The Suzuki coupling reaction forms a new C-C bond between R-X and R’-B(OR”)2 in presence of...The given synthesis: So the given synthesis is carried out below: In the first step, the...Structure of the target molecule is In the first step of the reaction, phenylmethanol (benzyl...The given synthesis is It is noticed that from the given starting material, a tertiary alcohol is...The given reaction is The carbonyl carbon in the ester substrate is partially positively charged,...The given reaction is The substrate is an acid chloride, the least stable of the carboxylic acid...The given reaction is So this is a saponification reaction of methyl cyclohexylmethanoate. In the...The given reactant is NaOH, followed by H3O+. The reactant is an acid chloride, which is the least...The given reactant is NaOH followed by H3O+. The product of the reaction will be a carboxylic acid,...The equation for the reaction of m-ethylbenzoyl chloride with (CH3CH2)2CuLi is: m-ethylbenzoyl...The equation for the reaction of methyl benzoate with LiAlH4, then H3O+ is: Methyl benzoate is an...The way of synthesis of the given compound by using acetyl chloride is as follows: Sodium benzoate...The given reaction is This is an example of a nucleophilic acyl substitution reaction in which an...This is an alcoholysis reaction. First step includes nucleophilic addition of alcohol to...In Step 1 of the mechanism, the acid protonates the ester’s carbonyl group, and in Step 2, water...The given reaction is Since water is a nucleophile, it attacks the electron deficient carbonyl...The reagent is a weak nucleophile H2O. It will add to one of the the carbonyl carbons of acetic...The given reaction is Alcohol is a weak nucleophile and adds to one of the carbonyl carbons of...The given molecule is The carboxylic acid formation requires water as a nucleophile in the...The equation for the reaction of methyl cyclohexylmethanoate with H2O, H+ is The methyl...The given reaction is: The ketone, substrate in the reaction, is asymmetrical ketone. carbonyl C is...The given compound is: The given compound is an ester that can be produced when a ketone treated...The given compound is, The disconnection of C-C bond at the α and β carbon of the given compound and...The reaction requires converting a carboxylic acid to an acid anhydride, which represents going up...The synthesis of ethyl acetate from acetic acid can be designed using retrosynthetic analysis. The...The rate law for reaction is R=k[E+][Benzene]. The general electrophilic aromatic substitution...The given reaction is Friedal Craft’s alkylation reaction. In the first step, AlCl3 acts as Lewis...The given reaction is It is noticed that the given substrate, phenol, is treated with ethyl chloride...The given equation is: In this aromatic compound, the benzene ring has sulfonyl group attached. The...The given pair of compounds is By using table 23-3, the –OH group is strongly activating than CH3,...The given pair is o-Dimethylbenzene and m-dimethylbenzene; structures for both are shown below: In...The given aromatic compound is: In this aromatic compound, the benzene ring has two methyl groups...The given aromatic compound is: In this aromatic compound, the benzene ring has two methyl groups...The given aromatic compound is: In this aromatic compound, the benzene ring has two methyl groups...The given molecule is: In the given molecule, benzene has two methoxy substituents. These are...The given trisubstituted target molecule is In the above molecule, CH3 is an ortho/para director,...The given reaction is The substrate has two aromatic rings, with an OH substituent on one ring. This...The given compound is: It is noticed that an electron-withdrawing carbonyl group is at meta-position...Diene here is ethene and dienophlile is but-1, 3-diene. These undergo [4+2] cycloaddition reaction....The given diol is The given diol is cis-1, 2-diol as both hydroxyl groups are on the same side of...(i) The given reaction is: In the above reaction, one reactant has 6π electrons and the second...The given reaction is: Here the diene is in trans configuration. For a Diels–Alder reaction to take...In this reaction, C=C reacts, indicated by a squiggly line. A syn 1, 2-diol is formed when C=C is...The product from this reaction is a syn 1, 2-diol. A syn 1, 2-diol is formed when a C=C is treated...The given reaction is Hot, concentrated permanganate (KMnO4) will cleave the double bond, oxidizing...The given reaction is Hot, concentrated permanganate (KMnO4) will cleave the double bond, oxidizing...Reaction (i) is Assuming the larger reactant to be the diene in its lowest excited state, i.e., the...The given compound is So when this compound is heated, ethene gas is evolved and a product with...The given reaction is Since it is given that the mechanism for the given reaction consists of a...The homolysis of the C-C bond in ethane is given below: A single barbed arrow () is used to...The given compound with types of C-H bond is: Here different types of C-H bonds are present in the...The given compound is: In the above compound there are three types of C atom; methyl, secondary and...The given reaction is Irradiation of the reaction mixture with UV light leads to the formation of...Propane has two types of hydrogens, one attached to a primary carbon and one to a secondary carbon....The given synthesis is The direct conversion is not known. Therefore, the retrosynthesis analysis is...The peak in Spectrum A at m/z = 97 is from the loss of an ethyl radical fragment, and this is only...The given repeating unit is The repeating units are shown in parentheses. A new C-C single bond is...The given monomer is In the initiation step, homolysis of benzoyl peroxide takes place to form a...The mechanism for the propagation and its corresponding product for a given reaction is shown below:...The alkene reacts with OH- in a nucleophilic addition step to form a carbanion. The CN and CO2CH3...The structure of oxetane is as below: The oxetane is a four membered ether ring and is highly...Both steps step 1 and step 2 are same, the homolysis of the vinyl π bond in two styrene molecules....
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