Organic Chemistry-Package(Custom)4th EditionSMITH Publisher: MCGISBN: 9781259141089
Organic Chemistry-Package(Custom)
Solutions for Organic Chemistry-Package(Custom)
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 the acid and base, and the conjugate acid and base in the following reactions. Use curved...Problem 2.4P:
Draw the products of each proton transfer reaction.Problem 2.5P:
Draw the products formed from the acid-base reaction of HCI with each compound. a.CH3OH b.CH3CH22O...Problem 2.6P:
Which compound in each pair is the stronger acid? a. CH3CH2CH3 or CH3CH2OHb. or pKa=50pKa=16...Problem 2.7P:
Use a calculator when necessary to answer the following questions. a.What is the pKa for each Ka:...Problem 2.8P:
Rank the conjugate bases of each of group of acids in order of increasing basicity. a NH3,H2O, CH4....Problem 2.9P:
Problem-2.10 Considers two acids: (formic acid,) and pivalic acid
. (a) Which acid has the larger ?...Problem 2.10P:
Estimate the pKa of each of the indicated bonds.Problem 2.13P:
Without reference to a pKa table, decide which compound in each pair is the stronger acid. a. NH3 or...Problem 2.14P:
which compound in each pair of isomers is the stronger acid?Problem 2.16P:
Which hydrogen in pseudoephedrine, the nasal decongestant in the commercial medication Sudafed, is...Problem 2.17P:
whichcompound in each pair is the stronger acid? a ClCH2COOH or FCH2COOH b ClCHCH2COOH or...Problem 2.18P:
Glycolic acid, HOCH2CO2H, is the simplest member of a group of compounds called - hydroxy acids...Problem 2.19P:
Explain the apparent paradox. HBr is a stronger acid than HCl, but HOCl is a stronger acid than...Problem 2.20P:
The CH bond in acetone, (CH3)2C=O, has a pKa of 19.2. Draw two resonance structures for its...Problem 2.21P:
Acetonitrile (CH3CN) has a pKa of 25, making it more acidic than many other compounds having only...Problem 2.22P:
For each pair of compounds: [1] Which indicated H is more acidic? [2] Draw the conjugate base of...Problem 2.23P:
Rank the compounds in each group in order of increasing acidity. a. CH3CH2CH3, CH3CH2OH, CH3CH2NH2...Problem 2.24P:
Which proton in each of the following drugs is most acidic? THC is the active component in...Problem 2.26P:
Problem 2.29
Compounds like amphetamine that contain nitrogen atoms are protonated by the in the...Problem 2.27P:
Problem 2.30 Which species are Lewis bases?
a. b. c. d.
Problem 2.28P:
Which species are Lewis acids?
a. b. c. d.
Problem 2.29P:
For each reaction, label the Lewis acid and base. Use curved arrow notation to show themovement of...Problem 2.33P:
2.36 Propranolol is an antihypertensive agent—that is, it lowers blood pressure. (a)
Which proton...Problem 2.34P:
2.37 Amphetamine is a powerful stimulant of the central nervous system. (a) Which
proton in...Problem 2.37P:
a Draw the conjugate acid of ethylene, CH2 = CH2. b Draw the conjugate base of ethylene.Problem 2.38P:
2.40 Draw the products formed from the acid-base reaction of H2SO4 with each
compound.
a. b. c....Problem 2.39P:
Draw the products formed from the acid-base reaction of KOH with each compound. a. b. c. d.Problem 2.41P:
Draw the product of acid-base reaction. a. c. b. d.Problem 2.44P:
What is Ka for each compound? Use a calculator when necessary. a. H2SpKa=7.0 b. ClCH2COOHpKa=2.8 c....Problem 2.45P:
What is the pKa for each compound? a. b. c.Problem 2.46P:
Which of the following bases are strong enough to deprotonate CH3CH2CH2CCH(pKa=25), so that...Problem 2.47P:
Which compounds can be deprotonated by OH, so that equilibrium favors the products? Refer to the pKa...Problem 2.48P:
Draw the product of each reaction. Use the pKa table in Appendix A to decide if the equilibrium...Problem 2.49P:
Rank the following compounds in order of increasing acidity. a. NH3, H2O, HFe. CH3OH, CH3NH2, CH3CH3...Problem 2.50P:
Rank the following ions in order of increasing basicity. a. CH3CH2,CH3O,CH3NHc. CH3COO-, CH3CH2O-,...Problem 2.53P:
The pKa of three CH bonds is given below. a. For each compound, draw the conjugate base, including...Problem 2.55P:
2.56 Draw the structure of a constitutional isomer of compound that fits each
description.
An...Problem 2.56P:
2.57 Many drugs are Bronsted-Lowry acids or bases.
a. What is the most acidic proton in the...Problem 2.57P:
Dimethyl ether (CH3OCH3) and ethanol (CH3CH2OH) are isomers, but has (CH3OCH3) a pKa of 40 and...Problem 2.59P:
Ethyl butanoate, CH3CH2CH2CO2CH2CH3, is one of the many organic compounds isolated from mangoes....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:
2.64 Classify each species as a Lewis acid, a Bronsted-Lowry acid, both, or neither.
a. b. C. d....Problem 2.65P:
Draw the products of each Lewis acid-base reaction. Label the electrophile and nucleophile. a.c.e....Problem 2.68P:
2.70 Hydroxide can react as a Brønsted-Lowry base (and remove a proton), or a
Lewis base (and...Problem 2.69P:
2.71 Answer the following questions about esmolol, a drug used to treat high blood pressure sold...Problem 2.71P:
2.72 DBU, is a base we will encounter in elimination
reaction in chapter 8, Which N atom is more...Problem 2.72P:
2.73 Molecules like acetamide can be protonated on either their or atoms
when treated with a...Problem 2.73P:
Two pKa values are reported for malonic acid, a compound with two COOH groups. Explain why one pKa...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 - LipidsChapter 31 - Synthetic Polymers
Book Details
Smith's
Organic Chemistry continues to breathe new life into the organic chemistry world. This new fourth edition retains its popular delivery of organic chemistry content in a student-friendly format. Janice Smith draws on her extensive teaching background to deliver organic chemistry in a way in which students learn: with limited use of text paragraphs, and through concisely written bulleted lists and highly detailed, well-labeled “teaching” illustrations. Don’t make your text decision without seeing
Organic Chemistry, 4th edition by Janice Gorzynski Smith!
Sample Solutions for this Textbook
We offer sample solutions for Organic Chemistry-Package(Custom) homework problems. See examples below:
Chapter 1, Problem 1.1PChapter 1, Problem 1.7PChapter 1, Problem 1.38PChapter 1, Problem 1.41PChapter 1, Problem 1.43PLewis structures can be drawn by following the below rules. • Draw a carbon back bone of the...For the hybridization, count the number of groups present around each atom. For example 4 groups =...The given compound is, Figure 1 In bond [1], there are four 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 1.82PChapter 2, Problem 2.1PThe given acid is HCN. An acid is a substance that is capable to donate a H+ ion or a proton. The...The given starting material CH3OH will acts as an acid and gives it proton to the base N−H2 to from...Chapter 2, Problem 2.44PChapter 2, Problem 2.45PChapter 2, Problem 2.48PChapter 2, Problem 2.49PChapter 2, Problem 2.69PThe reaction of CH3CH2OH with H2SO4 is given as, Figure 1 The reaction of ethanol (CH3CH2OH) with...Chapter 3, Problem 3.3PChapter 3, Problem 3.23PThe CH3CH3, ethane consists of only C – H and C – C bonds and these bonds are nonpolar thus the...The given compounds are CH3(CH2)4I, CH3(CH2)5I, CH3(CH2)6I. Boiling point depends upon the...The CBr3CH3 molecule consists of C – H, C – C and C – Br bonds among which C – Br bond is polar...The given hydrocarbons of sex pheromone are saturated acyclic alkanes. The aliphatic hydrocarbons...Chapter 4, Problem 4.9PChapter 4, Problem 4.10PChapter 4, Problem 4.33PChapter 4, Problem 4.39PChapter 4, Problem 4.41PThe given IUPAC name is 2,2−dimethyl−4−ethylheptane. The structure corresponding to the given IUPAC...Chapter 4, Problem 4.78PCellulose is a polysaccharide with a molecular formula (C6H10O5)n. It is formed by the monomers of...Chapter 5, Problem 5.27PThe priority can be assigned by numbering the groups which are bonded to the chiral carbon atom...The structure of given compoundis shown below. Figure 1 The stereochemistry of the compound is...Chapter 5, Problem 5.56PThe given Newman projection A is, Figure 1 In Newman projection, the circle represents the back...The given pair of compounds is, Figure 1 The given compounds have same connectivity of atoms or...The specific rotation [α] of pure quinine is −165. [α] value for the solution is −50. The...The given transformation is shown as, Figure 1 In the above reaction, the hydroxyl group is replaced...Chapter 6, Problem 6.7PThe given statement is “the reaction is faster than a reaction with Keq=8 and Ea=80 kJ/mol”. The...The chemical equation for the given reaction is, H3C−CH3+Br−Br→H3C−CH2−Br+HBr The bond dissociation...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 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 7.26PTo write the corresponding structure. To work backward from a name to the structure. First find the...On moving right to left across a row in periodic table, nucleophilicity as well as the basicity...Chapter 7, Problem 7.57PChapter 7, Problem 7.64PThe structure of the given alkyl halide shows that a carbon atom, on which bromine is present, is...Chapter 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 8.54PChapter 8, Problem 8.55PThe elimination of the Br from the reactant using base to form the respective alkene.Chapter 8, Problem 8.58PChapter 8, Problem 8.70PChapter 9, Problem 9.1PThe given reagent is SOCl2, pyridine. Alkyl chlorides are obtained by the reaction of 1ο or 2ο...Chapter 9, Problem 9.36PThe 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 9.46PChapter 9, Problem 9.48PThe given reagent is HBr. Hydrogen bromide (HBr) is a strong acid. The opening of an...Chapter 9, Problem 9.71PThe given molecular formula of the compound is C5H10. The first possible structure of alkene with...Chapter 10, Problem 10.2PChapter 10, Problem 10.37PChapter 10, Problem 10.40PChapter 10, Problem 10.41PChapter 10, Problem 10.51PChapter 10, Problem 10.54PHydration of alkenes is one of the methods used for the formation of alcohol. The general steps...Chapter 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 11.36PChapter 11, Problem 11.40PThe reaction of hept−1−yne with two equivalents of HBr is shown as, Figure 1 The reaction of...Chapter 11, Problem 11.60PThe 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 12.40PReduction of an alkene by the addition of H2 to one or both of the pi bonds. When an alkene is...Chapter 12, Problem 12.46PSynthesis of the given compound is shown below. Figure 1 In the first step, acetylene is converted...Chapter 13, Problem 13.1PChapter 13, Problem 13.18PChapter 13, Problem 13.24PChapter 13, Problem 13.26PChapter 13, Problem 13.33PChapter 13, Problem 13.40PChapter 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 14.17PChapter 14, Problem 14.35PSplitting pattern determines the kind of proton of proton in the structure. First determine if two...Chapter 14, Problem 14.50PThe 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 from cleavage of C−H bond in...Chapter 15, Problem 15.24PThe energy required to break the 1∘ C−H bond is more than the energy required to break the 2∘ C−H...Alkanes undergo chlorination when they are treated with Cl2 in the presence of light. Chlorination...Chapter 15, Problem 15.48PChapter 15, Problem 15.55PChapter 15, Problem 15.61PChapter 15, Problem 15.64PDiene 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 16.9PChapter 16, Problem 16.10PConjugated dienes undergoes electrophilic addition to gives a mixture of products that is...Chapter 16, Problem 16.37PThe given reaction is shown below. Figure 1 Diels-alder reaction is a cycloaddition reaction in...The given product is shown below. Figure 1 Diels-alder reaction is a cycloaddition reaction in which...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 17.28PChapter 17, Problem 17.29PChapter 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 aromatic compound on reaction with HNO3 in presence of H2SO4 undergoes nitration reaction. The...Chapter 18, Problem 18.36PAn aromatic compound undergoes Friedel-Craft acylation on reaction with ROCl in the presence of...Chapter 18, Problem 18.38PChapter 18, Problem 18.48PChapter 18, Problem 18.64PChapter 18, Problem 18.66PChapter 19, Problem 19.1PChapter 19, Problem 19.28PThe name of the compound is 3,3− dimethylpentanoic acid. The name suggests that the longest carbon...Chapter 19, Problem 19.35PChapter 19, Problem 19.36PChapter 19, Problem 19.37PChapter 19, Problem 19.40PChapter 19, Problem 19.56PThe 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 20.15PThe given reagents are organocuprate ((CH3)2CuLi) and organolithium (HC≡CLi). Organocuprate reagent...Chapter 20, Problem 20.38PThe halogen group of alkyl halide is replaced by Li when it is treated with Li. In the given...Chapter 20, Problem 20.40PThe reaction that shows the formation of product when α,β− unsaturated ketone reacts with NaBH4,...Chapter 20, Problem 20.44PChapter 21, Problem 21.1PThe given name is sec-butyl ethyl ketone. One should follow the given two steps to derive the...Chapter 21, Problem 21.42PChapter 21, Problem 21.43PIn the presence of sodium borohydride and methanol, phenylacetaldehyde gets reduced to...Chapter 21, Problem 21.48PChapter 21, Problem 21.57PChapter 21, Problem 21.59PChapter 21, Problem 21.60PChapter 21, Problem 21.81PThe classification of each amide group present in oxytocin as 1o, 2o, or 3o is shown as, Figure 1...The given treatment involves reaction of benzoic anhydride [(C6H5CO)2O] with H2O. Anhydrides involve...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 22.47PEsters do not undergo reaction with SOCl2. The replacement of RCOO− group of acid anhydride with Cl...Chapter 22, Problem 22.50PChapter 22, Problem 22.75PChapter 23, Problem 23.1PThe 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 the given compound with LDA in the presence of THF...Chapter 23, Problem 23.34PThe given compound is, Figure 1 The nucleophile −CH(CO2Et)2 attacks on the electrophilic centre of...Chapter 23, Problem 23.52PThe formation of the given product from cyclohexanone and organic halides having ≤4 C’s involves the...A chemical equation for the given synthesis is shown below. Figure 1 The formation of a given...The aldol product that formed by the given compound is shown below. Figure 1 In this aldol reaction,...The aldol product that is formed by the reaction of the two molecules of butanal in the presence of...Chapter 24, Problem 24.24PThe product that is formed by the aldol reaction of the given starting material(s) by using −OH, H2O...Chapter 24, Problem 24.40PChapter 24, Problem 24.46PChapter 24, Problem 24.48PChapter 24, Problem 24.67PThe given compound is shown below. Figure 1 In spermine, four nitrogen atoms are present. Among...The name of the given molecule suggests that a –NH2 is bonded to cyclobutane ring and cyclobutane...Chapter 25, Problem 25.54PThe given compound is benzyl bromide. The conversion of this to benzylamine occurs by using excess...Chapter 25, Problem 25.60PThe given reagent is HCl. The reaction of p-methylaniline (p-CH3C6H4NH2) with HCl is shown below....Amines on reaction with excess CH3I followed by Ag2O undergo Hofmann elimination. The major product...The given compound is shown below. Figure 1 Carbonyl compounds react with secondary amines in the...The product formed by the reaction of the given haloalkane with excess of ammonia is shown as,...Chapter 25, Problem 25.80PSpecies containing copper-carbon bonds are known as organocuprate reagents. These reagents act as...Chapter 26, Problem 26.32PChapter 26, Problem 26.43PChapter 26, Problem 26.44PChapter 26, Problem 26.45PChapter 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...The given product is shown below. Figure 1 Retro synthesis can be carried out to identify the diene...Chapter 27, Problem 27.50PThe 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 structure of D-talose is, Figure 1 The steps for the conversion of Fischer projection of...The given cyclic monosaccharide is, Figure 2 The steps for the conversion of Haworth projection into...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 l-isoleucine is, Figure 1 L-leucine has two stereogenic centers. Maximum number of...Chapter 29, Problem 29.28PChapter 29, Problem 29.36PChapter 29, Problem 29.37PChapter 29, Problem 29.38PChapter 29, Problem 29.40PThe product formed by the reaction of the given amino acid compound with methanol in the presence of...Chapter 30, Problem 30.1PChapter 30, Problem 30.11PChapter 30, Problem 30.28PChapter 30, Problem 30.29PChapter 30, Problem 30.38PThe 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 31, Problem 31.44PThe given alkene undergoes radical polymerization in presence of peroxide to form the polymer. The...
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