Noncovalent interactions (Section 2.12): One of a variety of nonbonding interactions between molecules, such as dipole-dipole forces, dispersion forces, and hydrogen bonds.
Nonessential amino acid (Section 26.1): One of the eleven amino acids that are biosynthesized by humans.
Normal alkanes (Section 3.2): Straight-chain alkanes, as opposed to branched alkanes. Normal alkanes are denoted by the suffix $n$, as in $n-\mathrm{C}_{4} \mathrm{H}_{10}$ ( $n$-butane).
NSAID (Chapter 15 Chemistry Matters): A nonsteroidal antiinflammatory drug, such as aspirin or ibuprofen.
Nuclear magnetic resonance (NMR) spectroscopy (Chapter 13 Introduction): A spectroscopic technique that provides information about the carbon-hydrogen framework of a molecule. NMR works by detecting the energy absorptions accompanying the transitions between nuclear spin states that occur when a molecule is placed in a strong magnetic field and irradiated with radiofrequency waves.
Nucleic acid (Section 28.1): Deoxyribonucleic acid (DNA) and ribonucleic acid (RNA); biological polymers made of nucleotides joined together to form long chains.
Nucleophile (Section 6.3, Section 6.4): An electron-rich species that donates an electron pair to an electrophile in a polar bondforming reaction. Nucleophiles are also Lewis bases.
Nucleophilic acyl substitution reaction (Section 21.2): A reaction in which a nucleophile attacks a carbonyl compound and substitutes for a leaving group bonded to the carbonyl carbon.
Nucleophilic addition reaction (Section 19.4): A reaction in which a nucleophile adds to the electrophilic carbonyl group of a ketone or aldehyde to give an alcohol.
Nucleophilic aromatic substitution reactions (Section 16.6): The substitution reactions of an aryl halide by a nucleophile.
Nucleophilic substitution reactions (Section 11.1): Reactions in which one nucleophile replaces another attached to a saturated carbon atom.


Amino acid (Section 26.1): See $\boldsymbol{\alpha}$-Amino acid. -

Nucleophilicity (Section 11.3): The ability of a substance to act as a nucleophile in an $\mathrm{S}_{\mathrm{N}} 2$ reaction.
Nucleoside (Section 28.1): A nucleic acid constituent consisting of a sugar residue bonded to a heterocyclic purine or pyrimidine base.
Nucleotides (Section 28.1): Nucleic acid constituents consisting of a sugar residue bonded both to a heterocyclic purine or pyrimidine base and to a phosphoric acid. Nucleotides are the monomer units from which DNA and RNA are constructed.
Nylons (Section 21.9): Synthetic polyamide step-growth polymers.
Okazaki fragments (Section 28.3): Short segments of a DNA lagging strand that is biosynthesized discontinuously and then linked by DNA ligases.
Olefin (Chapter 7 Introduction): An alternative name for an alkene.
Olefin metathesis polymerization (Section 31.5): A method of polymer synthesis based on using an olefin metathesis reaction.
Olefin metathesis reaction (Section 31.5): A reaction in which two olefins (alkenes) exchange substituents on their double bonds.
Oligonucleotides (Section 28.7): Short segments of DNA.
Optical isomers (Section 5.4): An alternative name for enantiomers. Optical isomers are isomers that have a mirrorimage relationship.
Optically active (Section 5.3): A property of some organic molecules wherein the plane of polarization is rotated through an angle when a beam of plane-polarized light is passed through a solution of the molecules.
Orbital (Section 1.2): A wave function, which describes the volume of space around a nucleus in which an electron is most likely to be found.
Organic chemistry (Chapter 1 Introduction): The study of carbon compounds.
Organohalides (Chapter 10 Introduction): Compounds that contain one or more halogen atoms bonded to carbon.
Organometallic compound (Section 10.6): A compound that contains a carbon-metal bond. Grignard reagents, RMgX, are examples.
Organophosphate (Section 1.10): A compound that contains a phosphorus atom bonded to four oxygens, with one of the oxygens also bonded to carbon.
Ortho (o) (Section 15.1): A naming prefix used for 1,2-disubstituted benzenes.
Oxidation (Section 8.7, Section 10.8): A reaction that causes a decrease in electron ownership by carbon, either by bond formation between carbon and a more electronegative atom (usually oxygen, nitrogen, or a halogen) or by bond-breaking between carbon and a less electronegative atom (usually hydrogen).
Oximes (Section 19.8): Compounds with the $\mathrm{R}_{2} \mathrm{C}=\mathrm{NOH}$
functional group.
Oxirane (Section 8.7): An alternative name for an epoxide.
Oxymercuration (Section 8.4): A method for double-bond hydration by reaction of an alkene with aqueous mercuric acetate followed by treatment with $\mathrm{NaBH}_{4}$.
Ozonide (Section 8.8): The product initially formed by addition of ozone to a carbon-carbon double bond. Ozonides are usually treated with a reducing agent, such as zinc in acetic acid, to produce carbonyl compounds.
Para (p) (Section 15.1): A naming prefix used for 1,4-disubstituted benzenes.
Paraffins (Section 3.5): A common name for alkanes.
Parent peak (Section 12.1): The peak in a mass spectrum corresponding to the molecular ion. The mass of the parent peak therefore represents the molecular weight of the compound.
Pauli exclusion principle (Section 1.3): No more than two electrons can occupy the same orbital, and those two must have spins of opposite sign.
Peptide bond (Section 26.4): An amide bond in a peptide chain.
Peptides (Chapter 26 Introduction): A type of short amino acid polymer in which the individual amino acid residues are linked by amide bonds.
Pericyclic reaction (Chapter 30 Introduction): A reaction that occurs in a single step by a reorganization of bonding electrons in a cyclic transition state.
Periplanar (Section 11.8): A conformation in which bonds to neighboring atoms have a parallel arrangement. In an eclipsed conformation, the neighboring bonds are syn periplanar; in a staggered conformation, the bonds are anti periplanar.
Peroxides (Section 18.1): Molecules containing an oxygen-oxygen bond functional group, ROOR' or ROOH.
Peroxyacid (Section 8.7): A compound with the $-\mathrm{CO}_{3} \mathrm{H}$ functional group. Peroxyacids react with alkenes to give epoxides.
Phenols (Chapter 17 Introduction): A class of compounds with an -OH group directly bonded to an aromatic ring, ArOH.
Phenoxide ion, $\mathrm{ArO}^{-}$(Section 17.2): The anion of a phenol.
Phenyl (Section 15.1): The name for the $-\mathrm{C}_{6} \mathrm{H}_{5}$ unit when the benzene ring is considered as a substituent. A phenyl group is abbreviated as -Ph.
Phosphine (Section 5.10): A trivalent phosphorus compound, $\mathrm{R}_{3} \mathrm{P}$.
Phosphite (Section 28.7): A compound with the structure $\mathrm{P}(\mathrm{OR})_{3}$.
Phospholipids (Section 27.3): Lipids that contain a phosphate residue. For example, glycerophospholipids contain a glycerol backbone linked to two fatty acids and a phosphoric acid.
Phosphoramidite (Section 28.7): A compound with the structure $\mathrm{R}_{2} \mathrm{NP}(\mathrm{OR})_{2}$.
Phosphoric acid anhydride (Section 29.1): A substance that contains $\mathrm{PO}_{2} \mathrm{PO}$ link, analogous to the $\mathrm{CO}_{2} \mathrm{CO}$ link in carboxylic acid anhydrides.

Photochemical reactions (Section 30.3): A reaction carried out by irradiating the reactants with light.
Physiological pH (Section 20.3): The pH of 7.3 that exists inside cells.
Pi ( $\boldsymbol{\pi}$ ) bond (Section 1.8): The covalent bond formed by sideways overlap of atomic orbitals. For example, carbon-carbon double bonds contain a $\pi$ bond formed by sideways overlap of two $p$ orbitals.
PITC (Section 26.6): Phenylisothiocyanate; used in the Edman degradation.
$\mathbf{p} K_{\mathbf{a}}$ (Section 2.8): The negative common logarithm of the $K_{\mathrm{a}}$; used to express acid strength.
Plane of symmetry (Section 5.2): A plane that bisects a molecule such that one half of the molecule is the mirror image of the other half. Molecules containing a plane of symmetry are achiral.
Plane-polarized light (Section 5.3): Light that has its electromagnetic waves oscillating in a single plane rather than in random planes. The plane of polarization is rotated when the light is passed through a solution of a chiral substance.
Plasticizers (Section 31.7): Small organic molecules added to polymers to act as a lubricant between polymer chains.
Polar aprotic solvents (Section 11.3): Polar solvents that can't function as hydrogen ion donors. Polar aprotic solvents such as dimethyl sulfoxide (DMSO) and dimethylformamide (DMF) are particularly useful in $\mathrm{S}_{\mathrm{N}} 2$ reactions because of their ability to solvate cations.
Polar covalent bond (Section 2.1): A covalent bond in which the electron distribution between atoms is unsymmetrical.
Polar reactions (Section 6.2, Section 6.3): Reactions in which bonds are made when a nucleophile donates two electrons to an electrophile and in which bonds are broken when one fragment leaves with both electrons from the bond.
Polarity (Section 2.1): The unsymmetrical distribution of electrons in a molecule that results when one atom attracts electrons more strongly than another.
Polarizability (Section 6.3): The measure of the change in a molecule's electron distribution in response to changing electrostatic interactions with solvents or ionic reagents.
Polycarbonates (Section 31.4): Polyesters in which the carbonyl groups are linked to two -OR groups, $\left[\mathrm{O}=\mathrm{C}(\mathrm{OR})_{2}\right]$.
Polycyclic (Section 4.9): Containing more than one ring.
Polycyclic aromatic compound (Section 15.6): A compound with two or more benzene-like aromatic rings fused together.
Polymer (Section 8.10, Section 21.9; Chapter 31 Introduction): A large molecule made up of repeating smaller units. For example, polyethylene is a synthetic polymer made from repeating ethylene units, and DNA is a biopolymer made of repeating deoxyribonucleotide units.
Polymerase chain reaction (PCR) (Section 28.8): A method for amplifying small amounts of DNA to produce larger amounts.
Polysaccharides (Section 25.9): A type of carbohydrate that is made of many simple sugars linked together by glycoside
(acetal) bonds.
Polyunsaturated fatty acids (Section 27.1): Fatty acids that contain more than one double bond.
Polyurethane (Section 31.4): A step-growth polymer prepared by reaction between a diol and a diisocyanate.
Posttranslational modification (Section 28.6): A chemical modification of a protein that occurs after translation from DNA.
Primary, secondary, tertiary, and quaternary (Section 3.3): Terms used to describe the substitution pattern at a specific site. A primary site has one organic substituent attached to it, a secondary site has two organic substituents, a tertiary site has three, and a quaternary site has four.


|  | Primary | Secondary | Tertiary | Quaternary |
| :--- | :--- | :--- | :--- | :--- |
| Carbon | $\mathrm{RCH}_{3}$ | $\mathrm{R}_{2} \mathrm{CH}_{2}$ | $\mathrm{R}_{3} \mathrm{CH}$ | $\mathrm{R}_{4} \mathrm{C}$ |
| Carbocation | $\mathrm{RCH}_{2}{ }^{+}$ | $\mathrm{R}_{2} \mathrm{CH}^{+}$ | $\mathrm{R}_{3} \mathrm{C}^{+}$ |  |
| Hydrogen | $\mathrm{RCH}_{3}$ | $\mathrm{R}_{2} \mathrm{CH}_{2}$ | $\mathrm{R}_{3} \mathrm{CH}$ |  |
| Alcohol | $\mathrm{RCH}_{2} \mathrm{OH}$ | $\mathrm{R}_{2} \mathrm{CHOH}$ | $\mathrm{R}_{3} \mathrm{COH}$ |  |
| Amine | $\mathrm{RNH}_{2}$ | $\mathrm{R}_{2} \mathrm{NH}$ | $\mathrm{R}_{3} \mathrm{~N}$ |  |


Primary structure (Section 26.9): The amino acid sequence in a protein.
pro- $\boldsymbol{R}$ (Section 5.11): One of two identical atoms or groups of atoms in a compound whose replacement leads to an $R$ chirality center.
pro-S (Section 5.11): One of two identical atoms or groups of atoms in a compound whose replacement leads to an $S$ chirality center.
Prochiral (Section 5.11): A molecule that can be converted from achiral to chiral in a single chemical step.
Prochirality center (Section 5.11): An atom in a compound that can be converted into a chirality center by changing one of its attached substituents.
Promoter sequence (Section 28.4): A short sequence on DNA located upstream of the transcription start site and recognized by RNA polymerase.
Propagation step (Section 8.10): A step in a radical chain reaction that carries on the chain. The propagation steps must yield both product and a reactive intermediate.
Prostaglandins (Section 27.4): Lipids derived from arachidonic acid. Prostaglandins are present in nearly all body tissues and fluids, where they serve many important hormonal functions.
Protecting group (Section 17.8, Section 19.10, Section 26.7): A group that is introduced to protect a sensitive functional group toward reaction elsewhere in the molecule. After serving its protective function, the group is removed.
Proteins (Chapter 26 Introduction): Large peptides containing


50 or more amino acid residues. Proteins serve both as structural materials and as enzymes that control an organism's chemistry.
Protein Data Bank (Chapter 26 Chemistry Matters): A worldwide online repository of X-ray and NMR structural data for biological macromolecules. To access the Protein Data Bank, go to https://www.rcsb.org (https://www.rcsb.org).
Protic solvents (Section 11.3): Solvents such as water or alcohol that can act as a proton donor.
Pyramidal inversion (Section 24.2): The rapid stereochemical inversion of a trivalent nitrogen compound.
Pyranose (Section 25.5): The six-membered, cyclic hemiacetal form of a simple sugar.
Quadrupole mass analyzer (Section 12.1): A type of mass spectrometer that uses four cylindrical rods to create an oscillating electrostatic field. Ion trajectories are determined by their $m / z$ ratios. At a given field, only one $m / z$ value will make it through the quadrupole region-the others will crash into the quadrupole rods or the walls of the instrument and never reach the detector.
Quartet (Section 13.6): A set of four peaks in an NMR spectrum, caused by spin-spin splitting of a signal by three adjacent nuclear spins.
Quaternary: See Primary.
Quaternary ammonium salt (Section 24.1): An ionic compound containing a positively charged nitrogen atom with four attached groups, $\mathrm{R}_{4} \mathrm{~N}^{+} \mathrm{X}^{-}$.
Quaternary structure (Section 26.9): The highest level of protein structure, involving an ordered aggregation of individual proteins into a larger cluster.
Quinone (Section 17.10): A 2,5-cyclohexadiene-1,4-dione.
$\boldsymbol{R}$ configuration (Section 5.5): The configuration at a chirality center as specified using the Cahn-Ingold-Prelog sequence rules.
$\mathbf{R}$ (Section 3.3): A generalized abbreviation for an organic partial structure.
Racemate (Section 5.8): A mixture consisting of equal parts (+) and (-) enantiomers of a chiral substance; also called a racemic mixture.
Radical (Section 2.6, Section 6.2): A species that has an odd number of electrons, such as the chlorine radical, $\mathrm{Cl} \cdot$.
Radical reactions (Section 6.2, Section 6.3): Reactions in which bonds are made by donation of one electron from each of two reactants and in which bonds are broken when each fragment leaves with one electron.
Rate constant (Section 11.2): The constant $k$ in a rate equation. Rate equation (Section 11.2): An equation that expresses the dependence of a reaction's rate on the concentration of reactants.
Rate-limiting step (Section 11.4): The slowest step in a multistep reaction sequence; also called the rate-determining step. The rate-limiting step acts as a kind of bottleneck in multistep reactions.


Re face (Section 5.11): One of two faces of a planar, $s p^{2}$-hybridized atom.
Rearrangement reactions (Section 6.1): What occurs when a single reactant undergoes a reorganization of bonds and atoms to yield an isomeric product.
Reducing sugars (Section 25.6): Sugars that reduce silver ion in the Tollens test or cupric ion in the Fehling or Benedict tests.
Reduction (Section 8.6, Section 10.8): A reaction that causes an increase of electron ownership by carbon, either by bondbreaking between carbon and a more electronegative atom or by bond formation between carbon and a less electronegative atom.
Reductive amination (Section 24.6, Section 26.3): A method for preparing an amine by reaction of an aldehyde or ketone with ammonia and a reducing agent.
Refining (Chapter 3 Chemistry Matters): The process by which petroleum is converted into gasoline and other useful products. Regiochemistry (Section 7.8): A term describing the orientation of a reaction that occurs on an unsymmetrical substrate.
Regiospecific (Section 7.8): A term describing a reaction that occurs with a specific regiochemistry to give a single product rather than a mixture of products.
Replication (Section 28.3): The process by which doublestranded DNA uncoils and is replicated to produce two new copies.
Replication forks (Section 28.3): The point of unraveling in a DNA chain where replication occurs.
Residues (Section 26.4): Amino acids in a protein chain.
Resolution (Section 5.8): The process by which a racemate is separated into its two pure enantiomers.
Resonance effect (Section 16.4): The donation or withdrawal of electrons through orbital overlap with neighboring $\pi$ bonds. For example, an oxygen or nitrogen substituent donates electrons to an aromatic ring by overlap of the O or N orbital with the aromatic ring $p$ orbitals.
Resonance forms (Section 2.4): Individual structural forms of a resonance hybrid.
Resonance hybrid (Section 2.4): A molecule, such as benzene, that can't be represented adequately by a single Kekulé structure but must instead be considered as an average of two or more resonance forms. The resonance forms themselves differ only in the positions of their electrons, not their nuclei.
Restriction endonucleases (Section 28.6): Enzymes that are able to cleave a DNA molecule at points in the chain where a specific base sequence occurs.
Retrosynthetic (Section 9.9, Section 16.10): Planning an organic synthesis by working backward from the final product to the starting material.
Ribonucleic acid (RNA) (Chapter 28 Introduction): The biopolymer found in cells that serves to transcribe the genetic information found in DNA and uses that information to direct the synthesis of proteins.


Ribosomal RNA (rRNA) (Section 28.4): A kind of RNA used in the physical makeup of ribosomes.
Ring-current (Section 15.7): The circulation of $\pi$ electrons induced in aromatic rings by an external magnetic field. This effect accounts for the downfield shift of aromatic ring protons in the ${ }^{1} \mathrm{H}$ NMR spectrum.
Ring-flip (Section 4.6): A molecular motion that interconverts two chair conformations of cyclohexane. The effect of a ringflip is to convert an axial substituent into an equatorial substituent.
Ring-opening metathesis polymerization (ROMP) (Section 31.5): A method of polymer synthesis that uses an olefin metathesis reaction of a cycloalkene.


RNA (Section 28.1): Ribonucleic acid.
Robinson annulation reaction (Section 23.12): A method for synthesis of cyclohexenones by sequential Michael reaction and intramolecular aldol reaction.
$\boldsymbol{S}$ configuration (Section 5.5): The configuration at a chirality center as specified using the Cahn-Ingold-Prelog sequence rules.
$\boldsymbol{s}$-Cis conformation (Section 14.5): The conformation of a conjugated diene that is cis-like around the single bond.
Saccharide (Section 25.1): A sugar.
Salt bridge (Section 26.9): An ionic attraction between two oppositely charged groups in a protein chain.
Sandmeyer reaction (Section 24.8): The nucleophilic substitution reaction of an arenediazonium salt with a cuprous halide to yield an aryl halide.
Sanger dideoxy method (Section 28.6): A commonly used method of DNA sequencing.
Saponification (Section 21.6, Section 27.2): An old term for the base-induced hydrolysis of an ester to yield a carboxylic acid salt.
Saturated (Section 3.2): A molecule that has only single bonds and thus can't undergo addition reactions. Alkanes are saturated, but alkenes are unsaturated.
Sawhorse representations (Section 3.6): A manner of representing stereochemistry that uses a stick drawing and gives a perspective view of the conformation around a single bond.
Schiff bases (Section 19.8, Section 29.5): An alternative name for an imine, $\mathrm{R}_{2} \mathrm{C}=\mathrm{NR}^{\prime}$, used primarily in biochemistry.
Second-order reaction (Section 11.2): A reaction whose ratelimiting step is bimolecular and whose kinetics are therefore dependent on the concentration of two reactants.


Secondary: See Primary. -

Secondary metabolite (Chapter 7 Chemistry Matters): A small naturally occurring molecule that is not essential to the growth and development of the producing organism and is not classified by structure.
Secondary structure (Section 26.9): The level of protein substructure that involves organization of chain sections into ordered arrangements such as $\beta$-pleated sheets or $\alpha$ helices.


Secondary: See Primary. -

Semiconservative replication (Section 28.3): The process by which DNA molecules are made containing one strand of old DNA and one strand of new DNA.
Sense strand (Section 28.4): The coding strand of doublehelical DNA that contains the gene.
Sequence rules (Section 5.5, Section 7.5): A series of rules for assigning relative rankings to substituent groups on a doublebond carbon atom or on a chirality center.


Secondary: See Primary. -

Sesquiterpenoids (Section 27.5): 15-carbon lipids.
Sharpless epoxidation (Chapter 19 Chemistry Matters): A method for enantioselective synthesis of a chiral epoxide by treatment of an allylic alcohol with tert-butyl hydroperoxide, $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{C}-\mathrm{OOH}$, in the presence of titanium tetraisopropoxide and diethyl tartrate.
Shielding (Section 13.2): An effect observed in NMR that causes a nucleus to absorb toward the right (upfield) side of the chart. Shielding is caused by donation of electron density to the nucleus.
Si face (Section 5.11): One of two faces of a planar, $s p^{2}$-hybridized atom.
Sialic acid (Section 25.7): One of a group of more than 300 carbohydrates based on acetylneuramic acid.
Side chain (Section 26.1): The substituent attached to the $\alpha$ carbon of an amino acid.
Sigma ( $\boldsymbol{\sigma}$ ) bond (Section 1.5): A covalent bond formed by headon overlap of atomic orbitals.
Sigmatropic reaction (Section 30.8): A pericyclic reaction that involves the migration of a group from one end of a $\pi$ electron system to the other.
Silyl ether (Section 17.8): A substance with the structure $\mathrm{R}_{3} \mathrm{Si}-\mathrm{O}-\mathrm{R}$. The silyl ether acts as a protecting group for alcohols.

Simmons-Smith reaction (Section 8.9): The reaction of an alkene with $\mathrm{CH}_{2} \mathrm{I}_{2}$ and $\mathrm{Zn}-\mathrm{Cu}$ to yield a cyclopropane.
Simple sugars (Section 25.1): Carbohydrates that cannot be broken down into smaller sugars by hydrolysis.
Single bond (Section 1.8): A covalent bond formed by sharing one electron pair between atoms.
Skeletal structures (Section 1.12): A shorthand way of writing structures in which carbon atoms are assumed to be at each intersection of two lines (bonds) and at the end of each line.
Small RNAs (Section 28.4): A type of RNA that has a variety of functions within the cell, including silencing transcription and catalyzing chemical modifications of other RNA molecules.
$\mathbf{S}_{\mathbf{N}} 1$ reaction (Section 11.4): A unimolecular nucleophilic substitution reaction.
$\mathrm{S}_{\mathrm{N}} 2$ reaction (Section 11.2): A bimolecular nucleophilic substitution reaction.
Solid-phase synthesis (Section 26.8): A technique of synthesis whereby the starting material is covalently bound to a solid polymer bead and reactions are carried out on the bound substrate. After the desired transformations have been effected, the product is cleaved from the polymer.


Secondary: See Primary. -

Solvation (Section 11.3): The clustering of solvent molecules around a solute particle to stabilize it.
$\boldsymbol{s p}$ hybrid orbitals (Section 1.9): Hybrid orbitals derived from the combination of an $s$ and a $p$ atomic orbital. The two $s p$ orbitals that result from hybridization are oriented at an angle of $180^{\circ}$ to each other.
$\boldsymbol{s p}^{2}$ hybrid orbitals (Section 1.8): Hybrid orbitals derived by combination of an $s$ atomic orbital with two $p$ atomic orbitals. The three $s p^{2}$ hybrid orbitals that result lie in a plane at angles of $120^{\circ}$ to each other.
$\boldsymbol{s p}^{\mathbf{3}}$ hybrid orbitals (Section 1.6): Hybrid orbitals derived by combination of an $s$ atomic orbital with three $p$ atomic orbitals. The four $s p^{3}$ hybrid orbitals that result are directed toward the corners of a regular tetrahedron at angles of $109^{\circ}$ to each other.
Specific rotation, [ $\boldsymbol{\alpha}] \mathbf{D}$ (Section 5.3): The optical rotation of a chiral compound under standard conditions.
Sphingomyelins (Section 27.3): Phospholipids that have sphingosine as the backbone rather than glycerol.
Spin-spin splitting (Section 13.6): The splitting of an NMR signal into a multiplet because of an interaction between nearby magnetic nuclei whose spins are coupled. The magnitude of spin-spin splitting is given by the coupling constant, J.
Staggered conformation (Section 3.6): The three-dimensional arrangement of atoms around a carbon-carbon single bond in which the bonds on one carbon bisect the bond angles on the second carbon as viewed end-on.
Statin (Chapter 29 Chemistry Matters): A drug that controls cholesterol biosynthesis in the body by blocking the HMG-CoA reductase enzyme.
Step-growth polymers (Section 21.9, Section 31.4): Polymers in which each bond is formed independently of the others. Polyesters and polyamides (nylons) are examples.
Stereocenter (Section 5.2): An alternative name for a chirality center.
Stereochemistry (Section 3.5; Chapters 3, 4, 5): The branch of chemistry concerned with the three-dimensional arrangement of atoms in molecules.
Stereogenic center (Section 5.2): An alternative name for a chirality center.
Stereoisomers (Section 4.2): Isomers that have their atoms connected in the same order but have different threedimensional arrangements. The term stereoisomer includes both enantiomers and diastereomers.
Stereospecific (Section 8.9, Section 14.5): A term indicating that only a single stereoisomer is produced in a given reaction rather than a mixture.
Steric strain (Section 3.7, Section 4.3, Section 4.7): The strain imposed on a molecule when two groups are too close together and try to occupy the same space. Steric strain is responsible both for the greater stability of trans versus cis alkenes and for the greater stability of equatorially substituted versus axially substituted cyclohexanes.

Steroids (Section 27.6): Lipids whose structure is based on a tetracyclic carbon skeleton with three 6 -membered and one 5 -membered ring. Steroids occur in both plants and animals and have a variety of important hormonal functions.
Stork enamine reaction (Section 23.11): The conjugate addition of an enamine to an $\alpha, \beta$-unsaturated carbonyl compound, followed by hydrolysis to yield a 1,5-dicarbonyl product.
STR loci (Chapter 28 Chemistry Matters): Short tandem repeat sequences of noncoding DNA that are unique to every individual and allow DNA fingerprinting.
Straight-chain alkanes (Section 3.2): Alkanes whose carbon atoms are connected without branching.
Substitution reactions (Section 6.1): What occurs when two reactants exchange parts to give two new products. $\mathrm{S}_{\mathrm{N}} 1$ and $\mathrm{S}_{\mathrm{N}} 2$ reactions are examples.
Sulfides (Section 3.1, Section 18.7): A class of compounds that has two organic substituents bonded to the same sulfur atom, RSR'.
Sulfonation (Section 16.2): The substitution of a sulfonic acid group $\left(-\mathrm{SO}_{3} \mathrm{H}\right)$ onto an aromatic ring.
Sulfone (Section 18.7): A compound of the general structure $\mathrm{RSO}_{2} \mathrm{R}^{\prime}$.
Sulfonium ions (Section 18.7): A species containing a positively charged, trivalent sulfur atom, $\mathrm{R}_{3} \mathrm{~S}^{+}$.
Sulfoxide (Section 18.7): A compound of the general structure RSOR'.
Suprafacial (Section 30.5): A word used to describe the geometry of pericyclic reactions. Suprafacial reactions take place on the same side of the two ends of a $\pi$ electron system.
Suzuki-Miyaura reaction (Section 10.7): The palladiumcatalyzed coupling reaction of an aromatic or vinylic halide with an aromatic or vinylic boronic acid.
Symmetry-allowed, symmetry-disallowed (Section 30.1): A symmetry-allowed reaction is a pericyclic process that has a favorable orbital symmetry for reaction through a concerted pathway. A symmetry-disallowed reaction is one that does not have favorable orbital symmetry for reaction through a concerted pathway.
Symmetry plane (Section 5.2): A plane that bisects a molecule such that one half of the molecule is the mirror image of the other half. Molecules containing a plane of symmetry are achiral.
Syn periplanar (Section 11.8): Describing a stereochemical relationship in which two bonds on adjacent carbons lie in the same plane and are eclipsed.
Syn stereochemistry (Section 8.5): The opposite of anti. A syn addition reaction is one in which the two ends of the double bond react from the same side. A syn elimination is one in which the two groups leave from the same side of the molecule. Syndiotactic (Section 31.2): A chain-growth polymer in which the stereochemistry of the substituents alternates regularly on opposite sides of the backbone.


Secondary: See Primary. -

Tautomers (Section 9.4, Section 22.1): Isomers that interconvert spontaneously, usually with the change in position of a hydrogen.


Secondary: See Primary. -

Terpenoids (Chapter 8 Chemistry Matters, Section 27.5): Lipids that are formally derived by head-to-tail polymerization of isoprene units.


Tertiary: See Primary -

Tertiary structure (Section 26.9): The level of protein structure that involves the manner in which the entire protein chain is folded into a specific three-dimensional arrangement.


Tertiary: See Primary -

Thermodynamic control (Section 14.3): An equilibrium reaction that yields the lowest-energy, most stable product is said to be thermodynamically controlled.


Tertiary: See Primary -

Thermoplastics (Section 31.7): Polymers that have a high $T_{\mathrm{g}}$ and are hard at room temperature but become soft and viscous when heated.


Tertiary: See Primary -

Thermosetting resins (Section 31.7): Polymers that become highly cross-linked and solidify into a hard, insoluble mass when heated.


Tertiary: See Primary -

Thioesters (Chapter 21 Introduction): A class of compounds with the RCOSR' functional group.
Thiols (Section 3.1, Chapter 18 Introduction): A class of compounds containing the -SH functional group.
Thiolate ion (Section 18.7): The anion of a thiol, $\mathrm{RS}^{-}$.
TMS (Section 13.3): Tetramethylsilane; used as an NMR calibration standard.


Tertiary: See Primary -

TOF (Section 12.4): Time-of-flight mass spectrometry; a sensitive method of mass detection accurate to about 3 ppm .
Tollens' reagent (Section 25.6): A solution of $\mathrm{Ag}_{2} \mathrm{O}$ in aqueous ammonia; used to oxidize aldehydes to carboxylic acids.
Torsional strain (Section 3.6, Section 4.3): The strain in a molecule caused by electron repulsion between eclipsed bonds. Torsional strain is also called eclipsing strain.
Tosylate (Section 11.1): A p-toluenesulfonate ester; useful as a leaving group in nucleophilic substitution reactions.
Transamination (Section 29.9): The exchange of an amino group and a keto group between reactants.
Transcription (Section 28.4): The process by which the genetic information encoded in DNA is read and used to synthesize RNA in the nucleus of the cell. A small portion of doublestranded DNA uncoils, and complementary ribonucleotides line up in the correct sequence for RNA synthesis.
Transfer RNA (tRNA) (Section 28.4): A kind of RNA that transports amino acids to the ribosomes, where they are joined together to make proteins.
Transimination (Section 29.9): The exchange of an amino group and an imine group between reactants.


Tertiary: See Primary -

Transition state (Section 6.9): An activated complex between reactants, representing the highest energy point on a reaction curve. Transition states are unstable complexes that can't be isolated.


Tertiary: See Primary -

Translation (Section 28.5): The process by which the genetic information transcribed from DNA onto mRNA is read by tRNA
and used to direct protein synthesis.
Tree diagram (Section 13.8): A diagram used in NMR to sort out the complicated splitting patterns that can arise from multiple couplings.
Triacylglycerols (Section 27.1): Lipids, such as those found in animal fat and vegetable oil, that are a triester of glycerol with long-chain fatty acids.


Tertiary: See Primary -

Tricarboxylic acid cycle (Section 29.7): An alternative name for the citric acid cycle by which acetyl CoA is degraded to $\mathrm{CO}_{2}$.


Tertiary: See Primary -

Triple bonds (Section 1.8): A type of covalent bond formed by sharing three electron pairs between atoms.


Tertiary: See Primary -

Triplet (Section 13.6): A symmetrical three-line splitting pattern observed in the ${ }^{1} \mathrm{H}$ NMR spectrum when a proton has two equivalent neighbor protons.


Tertiary: See Primary -

Turnover number (Section 26.10): The number of substrate molecules acted on by an enzyme molecule per unit time.
Twist-boat conformation (Section 4.5): A conformation of cyclohexane that is somewhat more stable than a pure boat conformation.


Tertiary: See Primary -

Ultraviolet (UV) spectroscopy (Section 14.7): An optical spectroscopy employing ultraviolet irradiation. UV spectroscopy provides structural information about the extent of $\pi$ electron conjugation in organic molecules.
Unimolecular reaction (Section 11.4): A reaction that occurs by spontaneous transformation of the starting material without the intervention of other reactants. For example, the dissociation of a tertiary alkyl halide in the $\mathrm{S}_{\mathrm{N}} 1$ reaction is a unimolecular process.
Unsaturated (Section 7.2): A molecule that has one or more multiple bonds.
Upfield (Section 13.3): The right-hand portion of the NMR chart.


Tertiary: See Primary -

Urethane (Section 31.4): A functional group in which a carbonyl group is bonded to both an -OR and an $-\mathrm{NR}_{2}$.
Uronic acid (Section 25.6): A monocarboxylic acid formed by oxidizing the $-\mathrm{CH}_{2} \mathrm{OH}$ end of an aldose without affecting the - CHO end


Tertiary: See Primary -

Valence bond theory (Section 1.5): A bonding theory that describes a covalent bond as resulting from the overlap of two atomic orbitals.
Valence shell (Section 1.4): The outermost electron shell of an atom.
van der Waals forces (Section 2.12): Intermolecular forces that are responsible for holding molecules together in the liquid and solid states.
Vegetable oils (Section 27.1): Liquid triacylglycerols derived from a plant source.
Vicinal (Section 9.2): A term used to refer to a 1,2-disubstitution pattern. For example, 1,2-dibromoethane is a vicinal dibromide.
Vinyl group (Section 7.3): $\mathrm{A}_{2} \mathrm{C}=\mathrm{CH}$ - substituent.
Vinyl monomer (Section 8.10, Section 31.1): A substituted alkene monomer used to make a chain-growth polymer.


Tertiary: See Primary -

Vinylic (Section 9.3): A term that refers to a substituent at a double-bond carbon atom. For example, chloroethylene is a vinylic chloride, and enols are vinylic alcohols.
Vitamin (Section 26.10): A small organic molecule that must be obtained in the diet and is required in trace amounts for proper growth and function.
Vulcanization (Section 14.6): A technique for cross-linking and hardening a diene polymer by heating with a few percent by weight of sulfur.
Walden inversion (Section 11.1): The inversion of configuration at a chirality center that accompanies an $\mathrm{S}_{\mathrm{N}} 2$ reaction.
Wave equation (Section 1.2): A mathematical expression that defines the behavior of an electron in an atom.
Wave function (Section 1.2): A solution to the wave equation for defining the behavior of an electron in an atom. The square of the wave function defines the shape of an orbital.
Wavelength, $\lambda$ (Section 12.5): The length of a wave from peak to peak. The wavelength of electromagnetic radiation is inversely proportional to frequency and inversely proportional to energy.
Wavenumber, $\widetilde{\boldsymbol{v}}$ (Section 12.6): The reciprocal of the wavelength in centimeters.
Waxes (Section 27.1): A mixture of esters of long-chain carboxylic acids with long-chain alcohols.
Williamson ether synthesis (Section 18.2): A method for synthesizing ethers by $\mathrm{S}_{\mathrm{N}} 2$ reaction of an alkyl halide with an alkoxide ion.
Wittig reaction (Section 19.11): The reaction of a phosphorus
ylide with a ketone or aldehyde to yield an alkene.
Wohl degradation (Section 25.6): A method for shortening the chain of an aldose sugar by one carbon.
Wolff-Kishner reaction (Section 19.9): The conversion of an aldehyde or ketone into an alkane by reaction with hydrazine and base.
X-ray crystallography (Chapter 12 Chemistry Matters): A technique that uses $X$ rays to determine the structure of molecules.
Ylide (Section 19.11): A neutral species with adjacent + and charges, such as the phosphoranes used in Wittig reactions.
$\boldsymbol{Z}$ geometry (Section 7.5): A term used to describe the stereochemistry of a carbon-carbon double bond. The two groups on each carbon are ranked according to the Cahn-Ingold-Prelog sequence rules, and the two carbons are compared. If the higher ranked groups on each carbon are on the same side of the double bond, the bond has $Z$ geometry.
Zaitsev's rule (Section 11.7): A rule stating that E2 elimination reactions normally yield the more highly substituted alkene as major product.
Ziegler-Natta catalysts (Section 31.2): Catalysts of an alkylaluminum and a titanium compound used for preparing alkene polymers.
Zwitterion (Section 26.1): A neutral dipolar molecule in which the positive and negative charges are not adjacent. For example, amino acids exist as zwitterions, $\mathrm{H}_{3} \stackrel{+}{\mathrm{N}}-\mathrm{CHR}-\mathrm{CO}_{2}{ }^{-}$


APPENDIX D -

Periodic Table
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1165.jpg?height=1131&width=1646&top_left_y=500&top_left_x=234)


ANSWER KEY -


Chapter 1 -

PROBLEM (a) $1 s^{2} 2 s^{2} 2 p^{4}$ (b) $1 s^{2} 2 s^{2} 2 p^{3}$ (c) $1 s^{2} 2 s^{2} 2 p^{6} 3 s^{6} 3 p^{4}$
1-1
PROBLEM (a) 2 (b) 2 (c) 6
1-2
PROBLEM
<img class="imgSvg" id = "m6sn3qkm94zanyold1q" src="data:image/svg+xml;base64,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"/>

PROBLEM
1-4
<img class="imgSvg" id = "m6sn3qkma2vmyr6fq1" src="data:image/svg+xml;base64,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"/>


Chapter 1 -

PROBLEM
(a) $\mathrm{CCl}_{4}$
(b) $\mathrm{AlH}_{3}$
(c) $\mathrm{CH}_{2} \mathrm{Cl}_{2}$
(d) $\mathrm{SiF}_{4}$
(e) $\mathrm{CH}_{3} \mathrm{NH}_{2}$


Chapter 1 -


Chapter 1 -

PROBLEM (a) O has 2 lone pairs and is $s p^{3}$-hybridized. (b) N has 1 lone pair and is $s p^{3}$-hybridized.
1-14 (c) P has 1 lone pair and is $s p^{3}$-hybridized. (d) S has 2 lone pairs and is $s p^{3}$-hybridized.


Chapter 1 -

PROBLEM (a)
1-15
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1167.jpg?height=299&width=445&top_left_y=829&top_left_x=474)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1167.jpg?height=340&width=500&top_left_y=822&top_left_x=989)


Chapter 1 -

Estrone $-\mathrm{C}_{18} \mathrm{H}_{22} \mathrm{O}_{2}$


Chapter 2 -

PROBLEM (a) H (b) Br (c) Cl (d) C
2-1
PROBLEM
(c)
$\mathrm{H}_{2}{ }_{\mathrm{S}}^{\mathrm{N}}-\mathrm{S}_{\mathrm{H}}{ }^{\delta+}$
(d) $\mathrm{H}_{3} \mathrm{C}-\mathrm{SH}$


Chapter 2 -

Carbon and sulfur have identical electronegativities.


Chapter 2 -


Chapter 2 -

PROBLEM The two $\mathrm{C}-\mathrm{O}$ dipoles cancel because of the symmetry of the molecule:
2-5
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1168.jpg?height=164&width=237&top_left_y=517&top_left_x=407)


Chapter 2 -

PROBLEM (a) For carbon: $\mathrm{FC}=4-8 / 2-0=0$ For the middle nitrogen: $\mathrm{FC}=5-8 / 2-0=+1$ For the end 2-7 nitrogen: $\mathrm{FC}=5-4 / 2-4=-1$
(b) For nitrogen: $\mathrm{FC}=5-8 / 2-0=+1$ For oxygen: $\mathrm{FC}=6-2 / 2-6=-1$
(c) For nitrogen: $\mathrm{FC}=5-8 / 2-0=+1$ For the triply bonded carbon: $\mathrm{FC}=4-6 / 2-2=-1$


Chapter 2 -

PROBLEM
2-8
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1168.jpg?height=218&width=305&top_left_y=1078&top_left_x=406)


Chapter 2 -

PROBLEM The structures in (a) are resonance forms.
2-9
PROBLEM (a)
2-10
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1168.jpg?height=191&width=866&top_left_y=1390&top_left_x=472)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1168.jpg?height=156&width=741&top_left_y=1581&top_left_x=475)
(c)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1168.jpg?height=75&width=586&top_left_y=1746&top_left_x=485)
(d)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1168.jpg?height=227&width=680&top_left_y=1746&top_left_x=1137)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1168.jpg?height=207&width=581&top_left_y=2016&top_left_x=1141)


Chapter 2 -

PROBLEM
2-11
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1168.jpg?height=146&width=652&top_left_y=2239&top_left_x=414)


Chapter 2 -

PROBLEM Phenylalanine is stronger.
2-12
PROBLEM Water is a stronger acid.


Chapter 2 -

2-13
PROBLEM Neither reaction will take place.
2-14
PROBLEM Reaction will take place.
2-15
PROBLEM $K_{\mathrm{a}}=4.9 \times 10^{-10}$
2-16
PROBLEM (a)
2-17
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1169.jpg?height=128&width=714&top_left_y=505&top_left_x=472)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1169.jpg?height=110&width=472&top_left_y=514&top_left_x=1252)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1169.jpg?height=118&width=1337&top_left_y=635&top_left_x=475)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1169.jpg?height=110&width=676&top_left_y=758&top_left_x=478)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1169.jpg?height=95&width=540&top_left_y=771&top_left_x=1248)


Chapter 2 -

PROBLEM Vitamin C is water-soluble (hydrophilic); vitamin A is fat-soluble (hydrophilic).


2-19 -


Chapter 3 -


PROBLEM -

3-3
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1169.jpg?height=256&width=695&top_left_y=2127&top_left_x=409)


PROBLEM -


PROBLEM -

PROBLEM
(a) Two (b) Four
(c) Four


PROBLEM -

PROBLEM Primary carbons have primary hydrogens, secondary carbons have secondary hydrogens, and 3-9 tertiary carbons have tertiary hydrogens.


PROBLEM -

PROBLEM
3-18
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1171.jpg?height=258&width=662&top_left_y=1779&top_left_x=417)


PROBLEM -

Chapter 4
PROBLEM (a) 1,4-Dimethylcyclohexane (b) 1-Methyl-3-propylcyclopentane (c) 3-Cyclobutylpentane
4-1 (d) 1-Bromo-4-ethylcyclodecane (e) 1-Isopropyl-2-methylcyclohexane
(f) 4-Bromo-1-tert-butyl-2-methylcycloheptane


PROBLEM -

1-Chloro-2,4-dimethylcyclohexane
(less stable chair form)
PROBLEM trans-Decalin is more stable because it has no 1,3-diaxial interactions.
4-20
PROBLEM Both ring-fusions are trans.
4-21
Chapter 5
PROBLEM Chiral: screw, shoe


PROBLEM -

PROBLEM Levorotatory
5-5
PROBLEM $+16.1^{\circ}$
5-6
PROBLEM (a) -Br
(b) -Br (c) $-\mathrm{CH}_{2} \mathrm{CH}_{3}$
(d) -OH
(e) $-\mathrm{CH}_{2} \mathrm{OH}$ (f) $-\mathrm{CH}=\mathrm{O}$


PROBLEM -

5-7
PROBLEM (a) $-\mathrm{OH},-\mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH},-\mathrm{CH}_{2} \mathrm{CH}_{3},-\mathrm{H}$ (b) $-\mathrm{OH},-\mathrm{CO}_{2} \mathrm{CH}_{3},-\mathrm{CO}_{2} \mathrm{H},-\mathrm{CH}_{2} \mathrm{OH}$
5-8 (c) $-\mathrm{NH}_{2},-\mathrm{CN},-\mathrm{CH}_{2} \mathrm{NHCH}_{3},-\mathrm{CH}_{2} \mathrm{NH}_{2}$ (d) $-\mathrm{SSCH}_{3},-\mathrm{SH},-\mathrm{CH}_{2} \mathrm{SCH}_{3},-\mathrm{CH}_{3}$
PROBLEM (a) $S$ (b) $R$ (c) $S$
5-9
PROBLEM (a) $S$ (b) $S$ (c) $R$
5-10
PROBLEM
5-11
<img class="imgSvg" id = "m6sn3qopr31sgl618gg" src="data:image/svg+xml;base64,PHN2ZyBpZD0ic21pbGVzLW02c24zcW9wcjMxc2dsNjE4Z2ciIHhtbG5zPSJodHRwOi8vd3d3LnczLm9yZy8yMDAwL3N2ZyIgdmlld0JveD0iMCAwIDE5MyA4OS4yNTAwNTUwOTQ2OTE1IiBzdHlsZT0id2lkdGg6IDE5My4xMTkyMDA4NzY4MTQ1NXB4OyBoZWlnaHQ6IDg5LjI1MDA1NTA5NDY5MTVweDsgb3ZlcmZsb3c6IHZpc2libGU7Ij48ZGVmcz48bGluZWFyR3JhZGllbnQgaWQ9ImxpbmUtbTZzbjNxb3ByMzFzZ2w2MThnZy0xIiBncmFkaWVudFVuaXRzPSJ1c2VyU3BhY2VPblVzZSIgeDE9IjEyMy44Mzk0MTEyNjA1OTEyOSIgeTE9IjUyLjUwMDAzNjcyOTc5NDM0IiB4Mj0iMTUxLjExOTIwMDg3NjgxNDU1IiB5Mj0iNjguMjUwMDU1MDk0NjkxNSI+PHN0b3Agc3RvcC1jb2xvcj0iY3VycmVudENvbG9yIiBvZmZzZXQ9IjIwJSI+PC9zdG9wPjxzdG9wIHN0b3AtY29sb3I9ImN1cnJlbnRDb2xvciIgb2Zmc2V0PSIxMDAlIj48L3N0b3A+PC9saW5lYXJHcmFkaWVudD48bGluZWFyR3JhZGllbnQgaWQ9ImxpbmUtbTZzbjNxb3ByMzFzZ2w2MThnZy0zIiBncmFkaWVudFVuaXRzPSJ1c2VyU3BhY2VPblVzZSIgeDE9Ijk2LjU1OTYwMDQzODQwNzI3IiB5MT0iNjguMjUwMDE4MzY0ODkwMDIiIHgyPSIxMjMuODM5NDExMjYwNTkxMjkiIHkyPSI1Mi41MDAwMzY3Mjk3OTQzNCI+PHN0b3Agc3RvcC1jb2xvcj0iY3VycmVudENvbG9yIiBvZmZzZXQ9IjIwJSI+PC9zdG9wPjxzdG9wIHN0b3AtY29sb3I9ImN1cnJlbnRDb2xvciIgb2Zmc2V0PSIxMDAlIj48L3N0b3A+PC9saW5lYXJHcmFkaWVudD48bGluZWFyR3JhZGllbnQgaWQ9ImxpbmUtbTZzbjNxb3ByMzFzZ2w2MThnZy01IiBncmFkaWVudFVuaXRzPSJ1c2VyU3BhY2VPblVzZSIgeDE9IjY5LjI3OTgxMDgyMjE4NDAyIiB5MT0iNTIuNDk5OTk5OTk5OTkyODYiIHgyPSI5Ni41NTk2MDA0Mzg0MDcyNyIgeTI9IjY4LjI1MDAxODM2NDg5MDAyIj48c3RvcCBzdG9wLWNvbG9yPSJjdXJyZW50Q29sb3IiIG9mZnNldD0iMjAlIj48L3N0b3A+PHN0b3Agc3RvcC1jb2xvcj0iY3VycmVudENvbG9yIiBvZmZzZXQ9IjEwMCUiPjwvc3RvcD48L2xpbmVhckdyYWRpZW50PjxsaW5lYXJHcmFkaWVudCBpZD0ibGluZS1tNnNuM3FvcHIzMXNnbDYxOGdnLTciIGdyYWRpZW50VW5pdHM9InVzZXJTcGFjZU9uVXNlIiB4MT0iNDIiIHkxPSI2OC4yNDk5ODE2MzUwODg1NSIgeDI9IjY5LjI3OTgxMDgyMjE4NDAyIiB5Mj0iNTIuNDk5OTk5OTk5OTkyODYiPjxzdG9wIHN0b3AtY29sb3I9ImN1cnJlbnRDb2xvciIgb2Zmc2V0PSIyMCUiPjwvc3RvcD48c3RvcCBzdG9wLWNvbG9yPSJjdXJyZW50Q29sb3IiIG9mZnNldD0iMTAwJSI+PC9zdG9wPjwvbGluZWFyR3JhZGllbnQ+PGxpbmVhckdyYWRpZW50IGlkPSJsaW5lLW02c24zcW9wcjMxc2dsNjE4Z2ctOSIgZ3JhZGllbnRVbml0cz0idXNlclNwYWNlT25Vc2UiIHgxPSI2OS4yNzk4MTA4MjIxODQwMiIgeTE9IjUyLjQ5OTk5OTk5OTk5Mjg2IiB4Mj0iNjkuMjc5ODMyMDI4MTQ0NzgiIHkyPSIyMSI+PHN0b3Agc3RvcC1jb2xvcj0iY3VycmVudENvbG9yIiBvZmZzZXQ9IjIwJSI+PC9zdG9wPjxzdG9wIHN0b3AtY29sb3I9ImN1cnJlbnRDb2xvciIgb2Zmc2V0PSIxMDAlIj48L3N0b3A+PC9saW5lYXJHcmFkaWVudD48L2RlZnM+PG1hc2sgaWQ9InRleHQtbWFzay1tNnNuM3FvcHIzMXNnbDYxOGdnIj48cmVjdCB4PSIwIiB5PSIwIiB3aWR0aD0iMTAwJSIgaGVpZ2h0PSIxMDAlIiBmaWxsPSJ3aGl0ZSI+PC9yZWN0PjxjaXJjbGUgY3g9IjY5LjI3OTgzMjAyODE0NDc4IiBjeT0iMjEiIHI9IjcuODc1IiBmaWxsPSJibGFjayI+PC9jaXJjbGU+PC9tYXNrPjxzdHlsZT4KICAgICAgICAgICAgICAgIC5lbGVtZW50LW02c24zcW9wcjMxc2dsNjE4Z2cgewogICAgICAgICAgICAgICAgICAgIGZvbnQ6IDE0cHggSGVsdmV0aWNhLCBBcmlhbCwgc2Fucy1zZXJpZjsKICAgICAgICAgICAgICAgICAgICBhbGlnbm1lbnQtYmFzZWxpbmU6ICdtaWRkbGUnOwogICAgICAgICAgICAgICAgfQogICAgICAgICAgICAgICAgLnN1Yi1tNnNuM3FvcHIzMXNnbDYxOGdnIHsKICAgICAgICAgICAgICAgICAgICBmb250OiA4LjRweCBIZWx2ZXRpY2EsIEFyaWFsLCBzYW5zLXNlcmlmOwogICAgICAgICAgICAgICAgfQogICAgICAgICAgICA8L3N0eWxlPjxnIG1hc2s9InVybCgjdGV4dC1tYXNrLW02c24zcW9wcjMxc2dsNjE4Z2cpIj48bGluZSB4MT0iMTIzLjgzOTQxMTI2MDU5MTI5IiB5MT0iNTIuNTAwMDM2NzI5Nzk0MzQiIHgyPSIxNTEuMTE5MjAwODc2ODE0NTUiIHkyPSI2OC4yNTAwNTUwOTQ2OTE1IiBzdHlsZT0ic3Ryb2tlLWxpbmVjYXA6cm91bmQ7c3Ryb2tlLWRhc2hhcnJheTpub25lO3N0cm9rZS13aWR0aDoxLjI2IiBzdHJva2U9InVybCgnI2xpbmUtbTZzbjNxb3ByMzFzZ2w2MThnZy0xJykiPjwvbGluZT48bGluZSB4MT0iOTYuNTU5NjAwNDM4NDA3MjciIHkxPSI2OC4yNTAwMTgzNjQ4OTAwMiIgeDI9IjEyMy44Mzk0MTEyNjA1OTEyOSIgeTI9IjUyLjUwMDAzNjcyOTc5NDM0IiBzdHlsZT0ic3Ryb2tlLWxpbmVjYXA6cm91bmQ7c3Ryb2tlLWRhc2hhcnJheTpub25lO3N0cm9rZS13aWR0aDoxLjI2IiBzdHJva2U9InVybCgnI2xpbmUtbTZzbjNxb3ByMzFzZ2w2MThnZy0zJykiPjwvbGluZT48bGluZSB4MT0iNjkuMjc5ODEwODIyMTg0MDIiIHkxPSI1Mi40OTk5OTk5OTk5OTI4NiIgeDI9Ijk2LjU1OTYwMDQzODQwNzI3IiB5Mj0iNjguMjUwMDE4MzY0ODkwMDIiIHN0eWxlPSJzdHJva2UtbGluZWNhcDpyb3VuZDtzdHJva2UtZGFzaGFycmF5Om5vbmU7c3Ryb2tlLXdpZHRoOjEuMjYiIHN0cm9rZT0idXJsKCcjbGluZS1tNnNuM3FvcHIzMXNnbDYxOGdnLTUnKSI+PC9saW5lPjxsaW5lIHgxPSI0MiIgeTE9IjY4LjI0OTk4MTYzNTA4ODU1IiB4Mj0iNjkuMjc5ODEwODIyMTg0MDIiIHkyPSI1Mi40OTk5OTk5OTk5OTI4NiIgc3R5bGU9InN0cm9rZS1saW5lY2FwOnJvdW5kO3N0cm9rZS1kYXNoYXJyYXk6bm9uZTtzdHJva2Utd2lkdGg6MS4yNiIgc3Ryb2tlPSJ1cmwoJyNsaW5lLW02c24zcW9wcjMxc2dsNjE4Z2ctNycpIj48L2xpbmU+PGxpbmUgeDE9IjY5LjI3OTgxMDgyMjE4NDAyIiB5MT0iNTIuNDk5OTk5OTk5OTkyODYiIHgyPSI2OS4yNzk4MzIwMjgxNDQ3OCIgeTI9IjIxIiBzdHlsZT0ic3Ryb2tlLWxpbmVjYXA6cm91bmQ7c3Ryb2tlLWRhc2hhcnJheTpub25lO3N0cm9rZS13aWR0aDoxLjI2IiBzdHJva2U9InVybCgnI2xpbmUtbTZzbjNxb3ByMzFzZ2w2MThnZy05JykiPjwvbGluZT48L2c+PGc+PHRleHQgeD0iMTUxLjExOTIwMDg3NjgxNDU1IiB5PSI2OC4yNTAwNTUwOTQ2OTE1IiBjbGFzcz0iZGVidWciIGZpbGw9IiNmZjAwMDAiIHN0eWxlPSIKICAgICAgICAgICAgICAgIGZvbnQ6IDVweCBEcm9pZCBTYW5zLCBzYW5zLXNlcmlmOwogICAgICAgICAgICAiPjwvdGV4dD48dGV4dCB4PSIxMjMuODM5NDExMjYwNTkxMjkiIHk9IjUyLjUwMDAzNjcyOTc5NDM0IiBjbGFzcz0iZGVidWciIGZpbGw9IiNmZjAwMDAiIHN0eWxlPSIKICAgICAgICAgICAgICAgIGZvbnQ6IDVweCBEcm9pZCBTYW5zLCBzYW5zLXNlcmlmOwogICAgICAgICAgICAiPjwvdGV4dD48dGV4dCB4PSI5Ni41NTk2MDA0Mzg0MDcyNyIgeT0iNjguMjUwMDE4MzY0ODkwMDIiIGNsYXNzPSJkZWJ1ZyIgZmlsbD0iI2ZmMDAwMCIgc3R5bGU9IgogICAgICAgICAgICAgICAgZm9udDogNXB4IERyb2lkIFNhbnMsIHNhbnMtc2VyaWY7CiAgICAgICAgICAgICI+PC90ZXh0Pjx0ZXh0IHg9IjY5LjI3OTgxMDgyMjE4NDAyIiB5PSI1Mi40OTk5OTk5OTk5OTI4NiIgY2xhc3M9ImRlYnVnIiBmaWxsPSIjZmYwMDAwIiBzdHlsZT0iCiAgICAgICAgICAgICAgICBmb250OiA1cHggRHJvaWQgU2Fucywgc2Fucy1zZXJpZjsKICAgICAgICAgICAgIj48L3RleHQ+PHRleHQgeD0iNDIiIHk9IjY4LjI0OTk4MTYzNTA4ODU1IiBjbGFzcz0iZGVidWciIGZpbGw9IiNmZjAwMDAiIHN0eWxlPSIKICAgICAgICAgICAgICAgIGZvbnQ6IDVweCBEcm9pZCBTYW5zLCBzYW5zLXNlcmlmOwogICAgICAgICAgICAiPjwvdGV4dD48dGV4dCB4PSI2NC4wMjk4MzIwMjgxNDQ3OCIgeT0iMjYuMjUiIGNsYXNzPSJlbGVtZW50LW02c24zcW9wcjMxc2dsNjE4Z2ciIGZpbGw9ImN1cnJlbnRDb2xvciIgc3R5bGU9IgogICAgICAgICAgICAgICAgdGV4dC1hbmNob3I6IHN0YXJ0OwogICAgICAgICAgICAgICAgd3JpdGluZy1tb2RlOiBob3Jpem9udGFsLXRiOwogICAgICAgICAgICAgICAgdGV4dC1vcmllbnRhdGlvbjogbWl4ZWQ7CiAgICAgICAgICAgICAgICBsZXR0ZXItc3BhY2luZzogbm9ybWFsOwogICAgICAgICAgICAgICAgZGlyZWN0aW9uOiBsdHI7CiAgICAgICAgICAgICI+PHRzcGFuPk88L3RzcGFuPjx0c3BhbiBzdHlsZT0idW5pY29kZS1iaWRpOiBwbGFpbnRleHQ7Ij5IPC90c3Bhbj48L3RleHQ+PHRleHQgeD0iNjkuMjc5ODMyMDI4MTQ0NzgiIHk9IjIxIiBjbGFzcz0iZGVidWciIGZpbGw9IiNmZjAwMDAiIHN0eWxlPSIKICAgICAgICAgICAgICAgIGZvbnQ6IDVweCBEcm9pZCBTYW5zLCBzYW5zLXNlcmlmOwogICAgICAgICAgICAiPjwvdGV4dD48L2c+PC9zdmc+"/>


PROBLEM -

PROBLEM $S$
5-12
PROBLEM Compound (a) is D-erythrose 4-phosphate, (d) is its enantiomer, and (b) and (c) are diastereomers.
5-13
PROBLEM Five chirality centers and $2^{5}=32$ stereoisomers
5-14
PROBLEM $S, S$
5-15
PROBLEM Compounds (a) and (d) are meso.
5-16
PROBLEM Compounds (a) and (c) have meso forms.
5-17
PROBLEM
5-18
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1173.jpg?height=234&width=321&top_left_y=2173&top_left_x=411)


PROBLEM -

PROBLEM Two diastereomeric salts: ( $R$ )-lactic acid plus ( $S$ )-1-phenylethylamine and ( $S$ )-lactic acid plus 5-20 (S)-1-phenylethylamine


PROBLEM -

PROBLEM (a) Constitutional isomers (b) Diastereomers
5-21
PROBLEM (a)
5-22
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1174.jpg?height=197&width=320&top_left_y=286&top_left_x=577)
(b) pro- $\mathrm{C} \longrightarrow$ pro-S


PROBLEM -

PROBLEM (S)-Lactate
5-24
PROBLEM The -OH adds to the Re face of C 2 , and -H adds to the Re face of C 3 . The overall addition has anti
5-25 stereochemistry.


Chapter 6 -

PROBLEM (a) Substitution (b) Elimination (c) Addition
6-1
PROBLEM (a) Carbon is electrophilic. (b) Sulfur is nucleophilic. (c) Nitrogens are nucleophilic.
6-2 (d) Oxygen is nucleophilic; carbon is electrophilic.
PROBLEM
6-3
PROBLEM Bromocyclohexane; chlorocyclohexane
6-4
PROBLEM
6-5
<img class="imgSvg" id = "m6sn3qoq4jvuayl8nev" src="data:image/svg+xml;base64,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"/>


Chapter 6 -

The mechanism is shown in Figure 6.4
PROBLEM (a)
6-6
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1174.jpg?height=76&width=638&top_left_y=1694&top_left_x=478)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1174.jpg?height=93&width=735&top_left_y=1791&top_left_x=478)
(c)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1174.jpg?height=172&width=722&top_left_y=1901&top_left_x=482)


Chapter 6 -

PROBLEM
6-7
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1175.jpg?height=457&width=760&top_left_y=208&top_left_x=409)


Chapter 6 -

PROBLEM 1-Chloro-2-methylpentane, 2-chloro-2-methylpentane, 3-chloro-2-methylpentane, 6-8 2-chloro-4-methylpentane, 1-chloro-4-methylpentane
PROBLEM
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1175.jpg?height=221&width=1302&top_left_y=773&top_left_x=346)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-1175.jpg?height=713&width=993&top_left_y=996&top_left_x=238)