Acetone, atom polarization

Acetone, (CH3)2C0, is widely used as an industrial solvent, (a) Draw the Lewis structure for the acetone molecule and predict the geometry around each carbon atom, (b) Is the acetone molecule polar or nonpolar (c) What kinds of intermoiecuiar attractive forces exist between acetone molecules (d) 1-Propanol, CH3CH2CH2OH, has a molecular weight that is very similar to that of acetone, yet acetone boils at 56.5 °C and 1-propanol boils at 97.2 °C. Explain the difference. 

Because of favorable dipole-dipole attractions between solvent molecules and solute molecules, polar liquids tend to dissolve in polar solvents. Water is both polar and able to form hydrogen bonds. (Section 11.2) Thus, polar molecules, especially those that can form hydrogen bonds with water molecules, tend to be soluble in water. For example, acetone, a polar molecule with the structural formula shown in the margin, mixes in all proportions with water. Acetone has a strongly polar C = O bond and pairs of nonbonding electrons on the O atom that can form hydrogen bonds with water. 

The solubihty of alkylphenols in water falls off precipitously as the number of carbons attached to the ring increases. They are generally soluble in common organic solvents acetone, alcohols, hydrocarbons, toluene. Solubihty in alcohols or heptane follows the generalization that "like dissolves like." The more polar the alkylphenol, the greater its solubihty in alcohols, but not in ahphatic hydrocarbons likewise with cresols and xylenols. The solubihty of an alkylphenol in a hydrocarbon solvent increases as the number of carbon atoms in the alkyl chain increases. High purity para substituted phenols, through Cg, can be obtained by crystallization from heptane. 

These effects can be attributed mainly to the inductive nature of the chlorine atoms, which reduces the electron density at position 4 and increases polarization of the 3,4-double bond. The dual reactivity of the chloropteridines has been further confirmed by the preparation of new adducts and substitution products. The addition reaction competes successfully, in a preparative sense, with the substitution reaction, if the latter is slowed down by a low temperature and a non-polar solvent. Compounds (12) and (13) react with dry ammonia in benzene at 5 °C to yield the 3,4-adducts (IS), which were shown by IR spectroscopy to contain little or none of the corresponding substitution product. The adducts decompose slowly in air and almost instantaneously in water or ethanol to give the original chloropteridine and ammonia. Certain other amines behave similarly, forming adducts which can be stored for a few days at -20 °C. Treatment of (12) and (13) in acetone with hydrogen sulfide or toluene-a-thiol gives adducts of the same type. 

Organic acids are characterized by the presence of a positively polarized hydrogen atom (blue in electrostatic potential maps) and are of two main kinds those acids such as methanol and acetic acid that contain a hydrogen atom bonded to an electronegative oxygen atom (O-H) and those such as acetone (Section 2.5) that contain a hydrogen atom bonded to a carbon atom next to a C=0 bond (Q=C-C-H). 

Aprotic means that the solvent does not have a proton on an electronegative atom. The solvent can still have hydrogen atoms, but none of them are connected to electronegative atoms. The most common examples of polar aprotic solvents are acetone, DMSO, DME, and DMF ... 

Acetone and CH3F contain electronegative atoms with nonbonding pairs, but neither has any highly polar H—X bonds. Thus, there is no hydrogen bonding between molecules of these substances. 

For a solution of ammonia in acetone, we must examine both components. Acetone has an electronegative oxygen atom with nonbonding pains, whereas NH3 has a polar N—bond. Consequently, a mixture of these two compounds displays hydrogen bonding between the hydrogen atoms of ammonia and oxygen atoms of acetone ... 

Iodo (trimethyl) platinum (IV) is a yellow crystalline product which decomposes at 190 to 195°. It is soluble in most nonpolar solvents and essentially insoluble in polar media such as water and acetone. In benzene solution, the iodo derivative is tetrameric.6 X-ray investigations have shown that in chloro-(trimethyl) platinum four platinum atoms describe a tetrahedron as do the four chlorine atoms, and the two tetrahedra are interpenetrating so as to give a cubic array of platinum and chlorine atoms. Each platinum atom is bonded to three chlorine atoms and to three terminal methyl groups. Some of the trimethylplatinum derivatives of organic chelate ligands are dimeric and in these structures the platinum is again six-coordinate.7... 

The lipids are a large and heterogeneous group of substances of biological origin that are easily dissolved in organic solvents such as methanol, acetone, chloroform, and benzene. By contrast, they are either insoluble or only poorly soluble in water. Their low water solubility is due to a lack of polarizing atoms such as 0, N, S, and P (see p.6). 

In polar and H-bonding solvents such as acetone, tetrahydrofuran or methanol CgQ is essentially insoluble. It is sparingly soluble in alkanes, with the solubility increasing with the number of atoms. In aromatic solvents and in carbon disulfide, in general appreciable solubilities are observed. A significant increase of the solubility takes place on going from benzenes to naphthalenes. Although there are trends for the solution behavior of Cjq, there is no direct dependence of the solubility on a certain solvent parameter like the index of refraction n. When the solubility is... 

Pyrido[2,3-, pyridazine derivatives 48 have been synthesized by refluxing equimolar amounts of an appropriate 5-benzylidene-2,2-dimethyl-l,3-dioxane-4,6-dione 47 with 5-amino-6-phenylpyridazin-3(2/7)-one 46 in methanol or a methanol acetic acid mixture. The electron-poor carbon atom of the polarized carbon-carbon double bond of 47 is the electrophile attacking C-4 of the 5-aminopyridazinone 46. Imino-enamine tautomerization of the intermediate is followed by ring closure and subsequent loss of acetone and carbon dioxide affording the reaction products 48 as stable crystalline solids in 70-90% yield (Scheme 9) <2000T2473>. 

The complex forms purple air-stable crystals and has good solubility in both polar and nonpolar solvents (e.g., acetone, dichloromethane, tetrahydro-furan, benzene, and hexane). It has been characterized crystallographically.7 The structure is an open, but folded, ladder-like array of six metal atoms with the two platinum atoms in the center. The IR spectrum (hexane) exhibits V(co> bands at 2085 (m), 2062 (vs), 2035 (vs), 2016 (w). Pt2Ru4(CO)18 has been found to be very useful for the synthesis of new platinum-ruthenium cluster complexes.10,12,13... 

Discrete dimers of the head-to-head type have been found in the structures of the Ag+ complex of (145)570 and the Na+ complex of (145)571 respectively. The complexes were recrystallized from carbon tetrachloride. In both complexes each metal is five-coordinated in the cavity provided by one anion, and there is an additional reaction with the second anion [through an Ag+-phenyl interaction or an Na+-carboxylate oxygen atom (Figure 32a)]. When the Na+ complex was crystallized from a solvent of medium polarity, acetone, the head-to-head dimer was recovered.571 In contrast, recrystallization from a polar medium, methanol, gave a monomeric complex in which one methanol of solvation was also present.572 In all of these complexes an intramolecular head-to-tail hydrogen bond was present to hold the ligand in its pseudo-macrocyclic conformation. 

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