chapter_1 introduction (1)

Slide 1

Definition: The study of carbon-containing molecules and their reactionsWhat happens to a molecule during a reaction?A collisionBonds break/formWHAT is a bond?The BIG question: WHY do reactions occur?We will need at least 2 semesters of your time to answer this question.FOCUS on the electrons.1.1 Organic ChemistryCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-11Why do we distinguish between organic and inorganic compounds?

Why are organic compounds important? 1.1 Organic ChemistryCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-2In the mid 1800s, it was first suggested that substances are defined by a specific arrangement of atoms.Why is a compounds formula NOT adequate to define it?

What term do we use to describe different substances with the same formula?1.2 Structural TheoryCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-3

Atoms that are most commonly bonded to carbon include N, O, H, and halides (F, Cl, Br, I).With some exceptions, each element generally forms a specific number of bonds with other atoms:

Practice with SKILLBUILDER 1.1.1.2 Structural TheoryCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-4

A covalent bond is a PAIR of electrons shared between two atoms. For example:

1.3 Covalent BondingCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-5

5How do potential energy and stability relate?

What forces keep the bond at the optimal length?

1.3 Covalent BondingCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-6

6A review from general chemistry:Protons (+1) and neutrons (neutral) reside in the nucleus.

Electrons (-1) reside outside the nucleus. WHERE?

Some electrons are close to the nucleus and others are far away. WHY?

Look at carbon for example. Which electrons are the valence electrons?

Why are valence electrons important?1.3 Covalent Bonding Atomic StructureCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-77You can always calculate the number of valence electron by analyzing the electronic configuration. Look at phosphorus.Or, for Group A elements only, just look at the group number (Roman numeral) on the periodic table.

Practice with SKILLBUILDER 1.2.1.3 Covalent Bonding Counting Valence ElectronsCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-8

8For simple Lewis structures:Draw the individual atoms using dots to represent the valence electrons.Put the atoms together so they share PAIRS of electrons to make complete octets. WHAT is an octet? Take NH3, for example:

Practice with SKILLBUILDER 1.3.1.3 Covalent Bonding Simple Lewis StructuresCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-9

9For simple Lewis structures:Draw the individual atoms using dots to represent the valence electrons.Put the atoms together so they share PAIRS of electrons to make complete octets. WHAT is an octet? Try drawing the structure for C2H2.

1.3 Covalent Bonding Simple Lewis StructuresCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-1010What term do we use to describe atoms with an unbalanced or FORMAL charge?How does formal charge affect the stability of an atom?Atoms in molecules (sharing electrons) can also have unbalanced charge, which must be analyzed because it affects stability.To calculate formal charge for an atom: Compare the number of valence electrons that SHOULD be associated with the atom to the number of valence electrons that are ACTUALLY associated with an atom.1.4 Formal ChargeCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-1111Consider the formal charge example below. Calculate the formal charge on each atom.

Carbon SHOULD have 4 valence electrons because it is in Group IVA on the periodic table.Carbon ACTUALLY has 8 valence electrons. It needs 8 for its octet, but only 4 count towards its charge. WHY?The 4 it ACTUALLY has balance out the 4 it SHOULD have, so it does not have a formal charge. Its neutral.1.4 Formal ChargeCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-12

or12Analyze the formal charge of the oxygen atom in the following:

Oxygen SHOULD have 6 valence electrons because it is in Group VIA on the periodic table.It ACTUALLY has 8 valence electrons. It needs 8 for its octet, but only 7 count towards its charge. WHY?If it ACTUALLY has 7, but it should only have 6, what is its formal charge?Practice with SKILLBUILDER 1.4.1.4 Formal ChargeCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-13

or13Covalent bonds are electron pairs that exist in an orbital shared between two atoms. What do you think that orbital looks like?

Just like an atomic orbital, the electrons could be anywhere within that orbital region.

What factors determine which atom in the bond will attract the shared electrons more?

1.5 Polar Covalent BondsCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-1414Covalent bonds are either polar or nonpolar:Nonpolar covalent bonds: bonded atoms share electrons evenlyPolar covalent bonds: one of the atoms attracts electrons more than the otherElectronegativity: How strongly an atom attracts shared electrons1.5 Polar Covalent BondsCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-15

15Electrons tend to shift away from lower electronegativity atoms to higher electronegativity atoms.

The greater the difference in electronegativity, the more polar the bond.1.5 Polar Covalent BondsCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-16

16Can a bond have both covalent and ionic character?

Practice with SKILLBUILDER 1.5.1.5 Polar Covalent BondsCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-1717General chemistry review:In the 1920s, quantum mechanics was established as a theory to explain the wave properties of electrons.The solution to wave equations for electrons provides us with visual pictures called orbitals.

1.6 Atomic OrbitalsCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-18

18General chemistry review:The type of orbital can be identified by its shape.An orbital is a region where there is a calculated 90% probability of finding an electron. The remaining 10% probability tapers off as you move away from the nucleus.


19Electrons behave as BOTH particles and waves. How can they be both? Maybe the theory is not yet complete.The theory does match experimental data, and it has predictive capability.Like a wave on a lake, an electrons wavefunction can be (+), (-), or ZERO.


Because they are generated mathematically from wavefunctions, orbital regions can also be (-), (+), or ZERO.The sign of the wave function has nothing to do with electrical charge. In this p-orbital, there is a nodal plane. The sign of the wavefunction will be important when we look at orbital overlapping in bonds.1.6 Atomic OrbitalsCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-2121Electrons are most stable (lowest in energy) if they are in the 1s orbital?The 1s orbital is full once there are two electrons in it. Why cant it fit more?The 2s orbital is filled next. The 2s orbital has a node. WHERE?

1.6 Atomic OrbitalsCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-2222Once the 2s is full, electrons fill into the three DEGENERATE 2p orbitals.Where are the nodes in each of the 2p orbitals?


23Common elements and their electron configurations:

Practice with SKILLBUILDER 1.6.1.6 Atomic OrbitalsCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-24

24What are the rules that govern our placement of electrons?


25A bond occurs when atomic orbitals overlap. Overlapping orbitals are like overlapping waves.

Only constructive interference results in a bond.

1.7 Valence Bond TheoryCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-26

26The bond for an H2 molecule results from constructive interference.

Where do the bonded electrons spend most of their time?

1.7 Valence Bond TheoryCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-2727

Atomic orbital wave functions overlap to form molecular orbitals (MOs) that extend over the entire molecule.MOs are a more complete analysis of bonds because they include both constructive and destructive interference.The number of MOs created must be equal to the number of atomic orbitals that were used.

1.8 Molecular Orbital TheoryCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-28H2 MOs28Why is the antibonding orbital higher in energy?

When the atomic orbitals overlap, why do the electrons go into the bonding MO rather than the antibonding MO?1.8 Molecular Orbital TheoryCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-29

H2 MOs29Imagine a He2 molecule. How would its MOs compare to those for H2?How would the energy of the He2 compare to 2 He?Why does helium exist in its atomic form rather than in molecular form?In general, if a molecule has all of it MOs occupied, will it be stable or unstable?1.8 Molecular Orbital TheoryCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-30

H2 MOs30Consider the MOs for CHBr3:

There are many areas of atomic orbital overlap.Notice how the MOs extend over the entire molecule.Each picture represents ONE orbital. 1.8 Molecular Orbital TheoryCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-31

31How many electrons can fit into the areas represented in (b)?

Depending on the circumstances, we will use both MO and valence bond theory to explain phenomena.1.8 Molecular Orbital TheoryCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-32

32

Given the electron configuration for C and H, imagine how their atomic orbitals might overlap.

Would such orbital overlap yield methane?1.9 Hybridized Atomic OrbitalsCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-33

33To make methane, the C atom must have 4 atomic orbitals available for overlapping.If an electron is excited from the 2s to the 2p, will that make it suitable for making methane?

If four H atoms were to come in and overlap with the 2s and 2p orbitals, what geometry would the resulting methane have?1.9 Hybridized Atomic OrbitalsCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-34

34The carbon must undergo hybridization to form four equal ATOMIC orbitals

The atomic orbitals must be equal in energy to form four equal-energy symmetrical C-H bonds.1.9 Hybridized Atomic OrbitalsCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-35

35Should the shape of an sp3 orbital look more like an s or more like p orbital?

1.9 Hybridized Atomic OrbitalsCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-36

36To make CH4, the 1s atomic orbitals of the H atoms will overlap with the four sp3 hybrid atomic orbitals of C.


37Draw a picture that shows the necessary atomic orbitals and their overlap to form ethane (C2H6).

Draw a picture that shows the necessary atomic orbitals and their overlap to form water.

Practice with CONCEPTUAL CHECKPOINT 1.19.1.9 Hybridized Atomic OrbitalsCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-3838

Consider ethene (ethylene).

Each carbon in ethene must bond to THREE other atoms, so only THREE hybridized atomic orbitals are needed.


39An sp2 hybridized carbon will have three equal-energy sp2 orbitals and one unhybridized p orbital.1.9 Hybridized Atomic OrbitalsCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-40

40The sp2 atomic orbitals overlap to form sigma () bonds.

Sigma bonds provide maximum HEAD-ON overlap.1.9 Hybridized Atomic OrbitalsCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-41

41The unhybridized p orbitals in ethene form pi () bonds, created by SIDE-BY-SIDE orbital overlap.


42MO theory provides a similar picture:Remember, red and blue regions are all part of the same orbital.


43Why is sp2 hybridization not appropriate for methane (CH4)?1.9 Hybridized Atomic OrbitalsCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-44

44Consider ethyne (acetylene).

Each carbon in ethyne must bond to TWO other atoms, so only TWO hybridized atomic orbitals are needed


45The sp atomic orbitals overlap HEAD-ON to form sigma () bonds while the unhybridized p orbitals overlap SIDE-BY-SIDE to form pi () bonds.

Practice with SKILLBUILDER 1.7.

1.9 Hybridized Atomic OrbitalsCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-4646Which should be stronger, a pi bond or a sigma bond? WHY?

Which should be stronger, an sp3sp3 sigma bond overlap or an spsp sigma bond overlap?

1.9 Hybridized Atomic OrbitalsCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-4747Explain the different strengths and lengths below.


48Valence shell electron pair repulsion (VSEPR theory):Valence electrons (bonded and lone pairs) repel each other.To determine molecular geometry:Determine the steric number.

1.10 Molecular GeometryCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-49

49To determine molecular geometry:Predict the hybridization of the central atom: If the steric number is 4, then it is sp3.If the steric number is 3, then it is sp2.If the steric number is 2, then it is sp.1.10 Molecular GeometryCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-50

50For any sp3 hybridized atom, the four valence electron pairs will form a TETRAHEDRAL ELECTRON GROUP geometry:Methane has four equal bonds, so the bond angles are equal.HOW does the lone pair of ammonia affect its geometry?The bond angles in oxygen are even smaller. WHY?1.10 Molecular Geometry sp3 GeometryCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-51

51The MOLECULAR geometry is different from the ELECTRON GROUP geometry. HOW?ExampleSteric numberHybridizationArrangement of electron pairsArrangement of atoms (geometry)CH44sp3TetrahedralTetrahedralNH34sp3TetrahedralTrigonal pyramidalH2O4sp3TetrahedralBent1.10 Molecular Geometry sp3 GeometryCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-52

52Calculate the steric number for BF3.Electron pairs that are located in sp2 hybridized orbitals will form a trigonal planar ELECTRON GROUP geometry.What will be the molecular geometry?

1.10 Molecular Geometry sp2 GeometryCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-5353How many electrons are in borons unhybridized p orbital? Does this geometry follow VSEPR theory?1.10 Molecular Geometry sp2 GeometryCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-54

54Analyze the steric number, hybridization, electron group geometry, and molecular geometry for this imine?1.10 Molecular Geometry sp2 GeometryCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-55

55Analyze the steric number, hybridization, electron group geometry, and the molecular geometry for the following molecules:BeH2

CO21.10 Molecular Geometry sp GeometryCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-5656Practice with SKILLBUILDER 1.8.1.10 Molecular Geometry SummaryCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-57

57Electronegativity differences cause induction.Induction (shifting of electrons WITHIN their orbitals) results in a dipole moment.Dipole moment = (the amount of partial charge) x (the distance the + and - are separated)Dipole moments are reported in units of debye (D)1 debye = 10-18 esu cmAn electrostatic unit of charge (esu) is a unit of charge. One electron has a charge of 4.80 x 10-10 esu.Centimeters (cm) are included in the unit because the distance between the centers of + and charges affects the dipole.1.11 Molecular PolarityCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-5858Consider the dipole for CH3ClDipole moment () = charge (e) x distance (d)Plug in the charge and distance = (1.056 x 10-10 esu) x (1.772 x 10-8 cm)Note that the amount of charge separation is less than what it would be if it were a full charge separation (4.80 x 10-10 esu). = 1.87 x 10-18 esu cmConvert to debye = 1.87 D

1.11 Molecular PolarityCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-59

59What would the dipole moment be if CH3Cl were 100% ionic? = charge (e) x distance (d)Plug in the charge and distance = (4.80 x 10-10 esu) x (1.772 x 10-8 cm)The full charge of an electron is plugged in = 8.51 x 10-18 esu cm = 8.51 D

What % of the C-Cl bond is ionic?Is the C-Cl bond mostly ionic or mostly covalent?1.11 Molecular PolarityCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-60

60Check out the polarity of come other common bonds:


61Why is the C=O double bond so much more polar than the CO single bond?1.11 Molecular PolarityCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-62

62For molecules with multiple polar bonds, the dipole moment is the vector sum of all of the individual bond dipoles.


63It is important to determine a molecules geometry FIRST before analyzing its polarity.If you have not drawn a molecule with the proper geometry, you may not assess the polarity correctly.Would the dipole for water be different if it were linear rather than angular?1.11 Molecular PolarityCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-64

64Electrostatic potential maps are often used to give a visual depiction of polarity.1.11 Molecular PolarityCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-65

651.11 Molecular PolarityPractice with SKILLBUILDER 1.9.Klein, Organic Chemistry 1e Copyright 2012 John Wiley & Sons, Inc.1-66

661.11 Molecular PolarityExplain why the dipole moment for pentane equal 0 D.Klein, Organic Chemistry 1e Copyright 2012 John Wiley & Sons, Inc.1-67

67Many properties such as solubility, boiling point, density, state of matter, melting point, etc. are affected by the attractions BETWEEN molecules.Neutral molecules (polar and nonpolar) are attracted to one another through:Dipoledipole interactionsHydrogen bondingDispersion forces (a.k.a. London forces or fleeting dipoledipole forces)

1.12 Intermolecular ForcesCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-6868Dipoledipole forces result when polar molecules line up their OPPOSITE charges.Note that acetones permanent dipole results from the difference in electronegativity between C and O.The dipoledipole attractions BETWEEN acetone molecules affects acetones boiling point (BP) and melting point (MP). HOW?

1.12 Intermolecular Forces DipoledipoleCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e

1-6969Why do isobutylene and acetone have such different MPs and BPs?1.12 Intermolecular Forces DipoledipoleCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-70

70Hydrogen bonds (H-bonds) are an especially strong type of dipoledipole attraction.Hydrogen bonds are strong because the partial + and charges are relatively large.Why are the partial charges in the H-bonding examples below relatively large?1.12 Intermolecular Forces Hydrogen BondingCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-71

71Only when a hydrogen shares electrons with a highly electronegative atom (O, N, F, or Cl) will it carry a large partial positive charge.The large + on the H atom can attract large charges on other molecules.Even with the large partial charges, H-bonds are still about 20 times weaker than covalent bonds.Compounds with H atoms that are capable of forming H-bonds are called PROTIC.

1.12 Intermolecular Forces Hydrogen BondingCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-72

72Which of the following solvents are PROTIC (capable of H-bonding), and which are not?

Acetic acid

Methylene chlorideDiethyl ether

Dimethyl sulfoxide1.12 Intermolecular Forces Hydrogen BondingCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-73

73Explain why the following isomers have different boiling points.1.12 Intermolecular Forces Hydrogen BondingCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-74

74If two molecules are nonpolar (dipole = 0 D), will they attract one another?YES. HOW?

Nonpolar molecules normally have their electrons (-) spread out evenly around the nuclei (+), completely balancing the charge.

However, the electrons are in constant random motion within their MOs.1.12 Intermolecular Forces London Dispersion ForcesCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-7575The constant random motion of the electrons in the molecule will sometimes produce an electron distribution that is NOT evenly balanced with the positive charge of the nuclei.Such uneven distribution produces a temporary dipole, which can induce a temporary dipole in a neighboring molecule.1.12 Intermolecular Forces London Dispersion ForcesCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-76

76The result is a fleeting attraction between the two molecules.

Such fleeting attractions are generally weak. However, like any weak attraction, if there are enough of them, they can add up to a lot.1.12 Intermolecular Forces London Dispersion ForcesCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-77

77

1.12 Intermolecular Forces London Dispersion ForcesCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-78The greater the surface area of a molecule, the more temporary dipole attractions are possible.Consider the feet of a gecko: They have many flexible hairs on their feet that maximize surface contact.The resulting London dispersion forces are strong enough to support the weight of the gecko.78Explain why molecules with more mass generally have higher boiling points.

Practice with SKILLBUILDER 1.10.1.12 Intermolecular Forces London Dispersion ForcesCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-79

79Explain why more highly branched molecules generally have lower boiling points.1.12 Intermolecular Forces London Dispersion ForcesCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-80

80We use the principle that like dissolves like.Polar compounds GENERALLY mix well with other polar compounds:If the compounds mixing are all capable of H-bonding and/or strong dipoledipole interactions, then there is no reason why they shouldnt mix.Nonpolar compounds GENERALLY mix well with other nonpolar compounds:If none of the compounds are capable of forming strong attractions, then no strong attractions would have to be broken to allow them to mix.1.13 SolubilityCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-8181We know it is difficult to get a polar compound (like water) to mix with a nonpolar compound (like oil):We cant use just water to wash oil off our dirty cloths.To remove nonpolar oils, grease, and dirt, we need soap.1.13 SolubilityCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-82

82Soap molecules organize into micelles in water, which form a nonpolar interior to carry away dirt.1.13 SolubilityCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-83

83Which attraction is generally stronger?The attraction between a permanent dipole and an induced or fleeting dipole,orThe attraction between a temporary dipole and an induced dipole (2 fleeting dipoles).Which attraction is generally stronger?The attraction between a polar molecule and a nonpolar molecule,orThe attraction between two nonpolar molecules?1.13 SolubilityCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-8484Why wont a nonpolar compound readily dissolve in water?

Is it because the water molecules repel the nonpolar molecules?1.13 SolubilityCopyright 2012 John Wiley & Sons, Inc.Klein, Organic Chemistry 1e 1-8585

chapter_1 introduction (1)

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