ORGANIC CHEMISTRY5th EditionSMITH Publisher: MCGISBN: 9781259977596
ORGANIC CHEMISTRY
Solutions for ORGANIC CHEMISTRY
Problem 2.1P:
a. Which compounds are Bronsted-Lowry acids: HBr,NH3,CCl4? b. Which compounds are Bronsted-Lowry...Problem 2.2P:
a. Draw the conjugate acid of each base: NH3,Cl,(CH3)2C=O. b. Draw the conjugate base of each acid:...Problem 2.3P:
Label each statement as True or False.
a. is the conjugate acid of.
b. is the conjugate base...Problem 2.4P:
Label the acid and base, and the conjugate acid and base in the following reactions. Use curved...Problem 2.5P:
Decide which compound is the acid and which is the base, and draw the products of each proton...Problem 2.6P:
Draw the products formed from the acid-base reaction of HCl with each compound. a.b. c. d.Problem 2.7P:
Which compound in each pair is the stronger acid? a. CH3CH2CH3 or CH3CH2OHb. or pKa=50pKa=16...Problem 2.8P:
Use a calculator when necessary to answer the following questions. a.What is the pKa for each Ka:...Problem 2.9P:
Rank the conjugate bases of each of group of acids in order of increasing basicity. a NH3,H2O, CH4....Problem 2.10P:
Problem-2.10 Considers two acids: (formic acid,) and pivalic acid
. (a) Which acid has the larger ?...Problem 2.12P:
Draw the products of each reaction and determine the direction of equilibrium. a.c. b.d.Problem 2.14P:
Without reference to a pKa table, decide which compound in each pair is the stronger acid. a. or b....Problem 2.16P:
Which hydrogen in each molecule is most acidic?
a. b. c.
Problem 2.17P:
Which hydrogen in pseudoephedrine, the nasal decongestant in the commercial medication Sudafed, is...Problem 2.20P:
Glycolic acid, HOCH2CO2H, is the simplest member of a group of compounds called - hydroxy acids...Problem 2.21P:
Explain the apparent paradox. HBr is a stronger acid than HCl, but HOCl is a stronger acid than...Problem 2.22P:
The CH bond in acetone, (CH3)2C=O, has a pKa of 19.2. Draw two resonance structures for its...Problem 2.23P:
Acetonitrile (CH3CN) has a pKa of 25, making it more acidic than many other compounds having only...Problem 2.24P:
For each pair of compounds: [1] Which indicated H is more acidic? [2] Draw the conjugate base of...Problem 2.26P:
Which proton in each of the following drugs is most acidic? THC is the active component in...Problem 2.27P:
Which anion A or B is the stronger base? ABProblem 2.29P:
Problem 2.29
Compounds like amphetamine that contain nitrogen atoms are protonated by the in the...Problem 2.30P:
Problem 2.30 Which species are Lewis bases?
a. b. c. d.
Problem 2.31P:
Which species are Lewis acids?
a. b. c. d.
Problem 2.32P:
For each reaction, label the Lewis acid and base. Use curved arrow notation to show the movement of...Problem 2.35P:
Label the Lewis acid and base. Use curved arrow notation to show the movement of electron pairs.Problem 2.36P:
2.36 Propranolol is an antihypertensive agent—that is, it lowers blood pressure. (a)
Which proton...Problem 2.37P:
2.37 Amphetamine is a powerful stimulant of the central nervous system. (a) Which
proton in...Problem 2.38P:
2.38 What is the conjugate acid of each base?
a. b. c. d.
Problem 2.39P:
2.39 What is the conjugate base of each acid?
a. b. c. d.
Problem 2.40P:
2.40 Draw the products formed from the acid-base reaction of H2SO4 with each
compound.
a. b. c....Problem 2.41P:
Draw the products formed from the acid-base reaction of KOH with each compound. a. b. c. d.Problem 2.42P:
Draw the products of each proton transfer reaction. Label the acid and base in the starting...Problem 2.45P:
What is Ka for each compound? Use a calculator when necessary. a. H2SpKa=7.0 b. ClCH2COOHpKa=2.8 c....Problem 2.46P:
What is the pKa for each compound? a. b. c.Problem 2.47P:
Which of the following bases are strong enough to deprotonate CH3CH2CH2CCH(pKa=25), so that...Problem 2.48P:
Which compounds can be deprotonated by OH, so that equilibrium favors the products? Refer to the pKa...Problem 2.49P:
Draw the products of each reaction. Use the pKa table in Appendix A to decide if the equilibrium...Problem 2.54P:
2.54 The of three bonds is given below.
a. For each compound, draw the conjugate base, including...Problem 2.56P:
2.56 Draw the structure of a constitutional isomer of compound that fits each
description.
An...Problem 2.57P:
2.57 Many drugs are Bronsted-Lowry acids or bases.
a. What is the most acidic proton in the...Problem 2.58P:
Dimethyl ether (CH3OCH3) and ethanol (CH3CH2OH) are isomers, but has (CH3OCH3) a pKa of 40 and...Problem 2.59P:
2.59 Atenolol is a (beta) blocker, a drug used to treat high blood pressure. Which of
the...Problem 2.60P:
2.60 Use the principles in Section 2.5 to label the most acidic hydrogen in each drug.
Explain your...Problem 2.61P:
2.61 Label the three most acidic hydrogen atoms in lactic acid. and
rank them in order of deceasing...Problem 2.63P:
2.63 Classify each compound as a Lewis base, a Bronsted-Lowry base, both, or neither.
a. b. c. d....Problem 2.64P:
2.64 Classify each species as a Lewis acid, a Bronsted-Lowry acid, both, or neither.
a. b. C. d....Problem 2.65P:
Label the Lewis acid and Lewis base in each reaction. Use curv ed arrows to show the movement of...Problem 2.66P:
2.66 Draw the products of each Lewis acid-base reaction. Label the electrophile and
nucleophile.
a....Problem 2.70P:
2.70 Hydroxide can react as a Brønsted-Lowry base (and remove a proton), or a
Lewis base (and...Problem 2.71P:
2.71 Answer the following questions about esmolol, a drug used to treat high blood pressure sold...Problem 2.72P:
2.72 DBU, is a base we will encounter in elimination
reaction in chapter 8, Which N atom is more...Problem 2.73P:
2.73 Molecules like acetamide can be protonated on either their or atoms
when treated with a...Browse All Chapters of This Textbook
Chapter 1 - Structure And BondingChapter 2 - Acids And BasesChapter 3 - Introduction To Organic Molecules And Functional GroupsChapter 4 - AlkanesChapter 5 - StereochemistryChapter 6 - Understanding Organic ReactionsChapter 7 - Alkyl Halides And Nucleophilic SubstitutionChapter 8 - Alkyl Halides And Elimination ReactionsChapter 9 - Alcohols, Ethers, And Related CompoundsChapter 10 - Alkenes
Chapter 11 - AlkynesChapter 12 - Oxidation And ReductionChapter 13 - Mass Spectrometry And Infrared SpectroscopyChapter 14 - Nuclear Magnetic Resonance SpectroscopyChapter 15 - Radical ReactionsChapter 16 - Conjugation, Resonance, And DienesChapter 17 - Benzene And Aromatic CompoundsChapter 18 - Reactions Of Aromatic CompoundsChapter 19 - Carboxylic Acids And The Acidity Of The O-h BondChapter 20 - Introduction To Carbonyl Chemistry; Organometallic Reagents; Oxidation And ReductionChapter 21 - Aldehydes And Ketones-nucleophilic AdditionChapter 22 - Carboxylic Acids And Their Derivatives-nucleophilic Acyl SubstitutionChapter 23 - Substitution Reactions Of Carbonyl Compounds At The α CarbonChapter 24 - Carbonyl Condensation ReactionsChapter 25 - AminesChapter 26 - Carbon–carbon Bond-forming Reactions In Organic SynthesisChapter 27 - Pericyclic ReactionsChapter 28 - CarbohydratesChapter 29 - Amino Acids And ProteinsChapter 30 - Synthetic PolymersChapter 31 - Lipids
Sample Solutions for this Textbook
We offer sample solutions for ORGANIC CHEMISTRY homework problems. See examples below:
Chapter 1, Problem 1.1PChapter 1, Problem 1.7PChapter 1, Problem 1.37PChapter 1, Problem 1.38PChapter 1, Problem 1.39PChapter 1, Problem 1.40PThe given compound is, Figure 1 In bond [1], there are three groups around C and no lone pair. Thus,...In hybridization, one 2s orbital is always used, but the number of 2p orbitals varies with the type...Chapter 1, Problem 1.77P
Chapter 2, Problem 2.1PChapter 2, Problem 2.45PChapter 2, Problem 2.46PChapter 2, Problem 2.48PChapter 2, Problem 2.49PChapter 2, Problem 2.51PIn the given reaction, Lewis base H2O reacts with Lewis acid (CH3CH2)3C+ . Electron pair present on...Chapter 2, Problem 2.71PThe reaction of CH3CH2OH with H2SO4 is given as, Figure 1 The reaction of ethanol (CH3CH2OH) with...Chapter 3, Problem 3.10PChapter 3, Problem 3.13PChapter 3, Problem 3.32PChapter 3, Problem 3.33PChapter 3, Problem 3.60PChapter 3, Problem 3.61PThe given hydrocarbons of sex pheromone are saturated acyclic alkanes. The aliphatic hydrocarbons...Chapter 4, Problem 4.7PChapter 4, Problem 4.8PChapter 4, Problem 4.34PChapter 4, Problem 4.38PChapter 4, Problem 4.40PThe given IUPAC name is 2,2−dimethyl−4−ethylheptane. The structure corresponding to the given IUPAC...Chapter 4, Problem 4.75PCellulose 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...Chapter 5, Problem 5.28PThe priority can be assigned by numbering the groups which are bonded to the chiral carbon atom...Chapter 5, Problem 5.47PThe 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...Chapter 6, Problem 6.1PChapter 6, Problem 6.9PThe 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...Chapter 6, Problem 6.53PChapter 7, Problem 7.1PThe 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...Chapter 7, Problem 7.23PChapter 7, Problem 7.53PChapter 7, Problem 7.58PChapter 7, Problem 7.59PThe structure of the given alkyl halide shows that a carbon atom, on which bromine is present, is...Chapter 7, Problem 7.76PChapter 8, Problem 8.1PE2type 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...Chapter 8, Problem 8.53PChapter 8, Problem 8.54PChapter 8, Problem 8.56PChapter 8, Problem 8.68PChapter 9, Problem 9.1PChapter 9, Problem 9.27PChapter 9, Problem 9.38PThe 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...Chapter 9, Problem 9.45PThe given reagent is HBr. Hydrogen bromide (HBr) is a strong acid. The opening of an...Chapter 9, Problem 9.65PThe 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...Chapter 10, Problem 10.2PThe compounds with same chemical formula but different arrangement of atoms in space are known as...Chapter 10, Problem 10.35PChapter 10, Problem 10.38PThe given IUPAC name is (E)−4−ethylhept−3−ene. Rules for writing structural formula from IUPAC are...Chapter 10, Problem 10.46PChapter 10, Problem 10.64PChapter 11, Problem 11.1PThe 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...Chapter 11, Problem 11.33PChapter 11, Problem 11.34PChapter 11, Problem 11.36PChapter 11, Problem 11.38PThe given reaction is, Figure 1 There is decrease in the number of C−O bonds. Hence, this is a...Chapter 12, Problem 12.7PChapter 12, Problem 12.29PFor compound A: Before hydrogenation, the molecular formula is C5H8. The maximum number of H's...Chapter 12, Problem 12.38PChapter 12, Problem 12.39PChapter 12, Problem 12.44PChapter 12, Problem 12.63PChapter 13, Problem 13.1PThe molecular formula of the compound is C4H9Cl. Chlorine atom has two isotopes 35Cl and 37Cl. The...Chapter 13, Problem 13.19PThe molecular formula of given compound is C6H6. The m/z value of C6H6 is calculated as, Mass of...Chapter 13, Problem 13.27PChapter 13, Problem 13.37PChapter 13, Problem 13.42PChapter 14, Problem 14.1PChapter 14, Problem 14.3PThe 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...Chapter 14, Problem 14.18PIn 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...Chapter 14, Problem 14.48PThe 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...Chapter 15, Problem 15.18PElectrophilic 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...Chapter 15, Problem 15.53PChapter 15, Problem 15.57PDiene 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...Chapter 16, Problem 16.10PChapter 16, Problem 16.11PChapter 16, Problem 16.16PChapter 16, Problem 16.32PChapter 16, Problem 16.37PConjugated 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...Chapter 17, Problem 17.27PChapter 17, Problem 17.28PChapter 17, Problem 17.53PChapter 17, Problem 17.55PChapter 17, Problem 17.56PBenzene 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...Chapter 18, Problem 18.22PChapter 18, Problem 18.38PChapter 18, Problem 18.47PChapter 18, Problem 18.49PChapter 18, Problem 18.63PThe numbering of carbon atoms in the given compound is shown below. Figure 1 The given compound has...Chapter 19, Problem 19.10PChapter 19, Problem 19.29PChapter 19, Problem 19.30PChapter 19, Problem 19.35PChapter 19, Problem 19.40PChapter 19, Problem 19.50PChapter 19, Problem 19.57PThe given structure of α- sinensal is, Figure 1 Bond [1] is formed by the overlapping of sp2 hybrid...Chapter 20, Problem 20.7PChapter 20, Problem 20.27PChapter 20, Problem 20.30PChapter 20, Problem 20.34PThe ball and stick model of compound A and B shows that black balls represent carbon atom, white...Chapter 20, Problem 20.38PChapter 20, Problem 20.39PThe reaction that shows the formation of product when α,β− unsaturated ketone reacts with NaBH4,...Chapter 21, Problem 21.1PThe 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...Chapter 21, Problem 21.43PChapter 21, Problem 21.44PChapter 21, Problem 21.46PChapter 21, Problem 21.74PThe classification of each amide group present in oxytocin as 1o, 2o, or 3o is shown as, Figure 1...Chapter 22, Problem 22.5PThe 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....Chapter 22, Problem 22.41PChapter 22, Problem 22.45PChapter 22, Problem 22.46PChapter 22, Problem 22.75PChapter 23, Problem 23.1PThe 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...Chapter 23, Problem 23.50PThe aldol product that formed by the given compound is shown below. Figure 1 In this aldol reaction,...Chapter 24, Problem 24.8PThe aldol product that is formed by the reaction of the two molecules of butanal in the presence of...Chapter 24, Problem 24.25PChapter 24, Problem 24.45PChapter 24, Problem 24.48PChapter 24, Problem 24.65PThe 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...Chapter 25, Problem 25.52PThe products formed when the given amine reacts with [1] CH3I(excess); [2] Ag2O are shown below....Chapter 25, Problem 25.55PSpecies containing copper-carbon bonds are known as organocuprate reagents. These reagents act as...Chapter 26, Problem 26.20PChapter 26, Problem 26.34PChapter 26, Problem 26.47PThe given compound is a diene. The ring-closing metathesis (RCM) by Grubbs catalyst occurs, when the...Chapter 26, Problem 26.49PThe given reaction is shown below. Figure 1 The sigma bond that is broken during the conversion of...Chapter 27, Problem 27.4PThe thermal electrocyclic ring closure reaction is shown below. Figure 1 Electrocyclic reactions...Chapter 27, Problem 27.41PThe product of the [3,3] sigmatropic rearrangement for the given compound is shown below. [a1]...Chapter 27, Problem 27.52PThe 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...Chapter 28, Problem 28.40PThe 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...Chapter 28, Problem 28.50PThe 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...Chapter 29, Problem 29.29PChapter 29, Problem 29.36PChapter 29, Problem 29.37PChapter 29, Problem 29.60PThe 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...Chapter 30, Problem 30.43PChapter 30, Problem 30.49PChapter 31, Problem 31.1PChapter 31, Problem 31.10PChapter 31, Problem 31.26PChapter 31, Problem 31.27PChapter 31, Problem 31.28PChapter 31, Problem 31.38P
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Study Guide/Solutions Manual for Organic Chemistry
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Loose Leaf for Organic Chemistry
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