Alcohol, phenol ,and ethers


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Alcohol, phenol ,and ethers

  1. 1. Alcohol, Phenol, And Ethers: “Their Structures, Physical Properties and Nomenclature” Mr. Blithe Topic:
  2. 2. Structure and Physical Properties ALCOHOL An organic compound containing a hydroxyl group attached to an alkyl group. a non-polar (alkane-like) chain. a polar hydroxyl group. Alcohols have the general formula: R-OH, where “R” involves a saturated C-atom (bound to hydrogen's and/or other carbons). For example:
  3. 3. Classification of alcohols • Alcohols may be classified as 1o (Primary), 2o (Secondary), or 3o (Tertiary), by considering the number of carbons bound to the hydroxyl-bearing carbon. •Ethanol is a primary alcohol because there is only one alkyl group attached to the carbon that carries the OH substituent. •The isopropyl alcohol found in rubbing alcohol is a secondary alcohol, •An example of a tertiary alcohol is tert-butyl (or t-butyl) alcohol or 2-methyl-2-propanol. RCH2OH R3COHR2CHOH
  4. 4. R-O-H has a structure similar to that of water Higher boiling points. Hydrogen Bond in Water Hydrogen Bond in Alcohol
  5. 5. Classification of alcohols Solubility The Lower the molecular weight of alcohols, the higher the solubility in water. The water-solubility of alcohols depends on the length of the alkyl chain in the alcohol. alcohols having chains longer than four carbons are not very water-soluble. 3-4 carbons or less— ARE soluble in water Alcohols with more than one hydroxyl group (polyhydroxyl alcohols) have higher boiling points than monohydroxyl alcohols. We already saw that the boiling points of alkanes increase with increasing chain length. The same is true for alcohols.
  6. 6. O CH3 H O CH3 H Alcohols having chains SHORTER than four carbons are very water-soluble…  Methanol is Soluble and Miscible in water… Methanol
  7. 7. Butanol Alcohols having chains LONGER than Three carbons are not very water-soluble…  Butanol is Soluble but not Miscible in water…
  8. 8. Formula Name Solubility in Water (g/100 g) CH3OH methanol infinitely soluble CH3CH2OH ethanol infinitely soluble CH3(CH2)2OH propanol infinitely soluble CH3(CH2)3OH butanol 9 CH3(CH2)4OH pentanol 2.7 CH3(CH2)5OH hexanol 0.6 CH3(CH2)6OH heptanol 0.18 CH3(CH2)7OH octanol 0.054 CH3(CH2)9OH decanol insoluble in water Solubilities of ALCOHOL in water
  9. 9. CH3CH2 CH2OH CH3CH2 CH2CH3 CH3OH CH3CH3 CH3CH2 OH CH3CH2 CH3 CH3CH2 CH2CH2OH CH3CH2 CH2CH2CH3 Structural Formula Name Molecular Weight bp (°C) Solubility in Water methanol 32 65 infinite ethane 30 -89 insoluble ethanol 46 78 infinite propane 44 -42 insoluble 1-propanol 60 97 infinite butane 58 0 insoluble 8 g/100 g117741-butanol pentane 72 36 insoluble Comparison between the Boiling points and Solubility of ALKANES and ALCOHOLs
  10. 10. PHENOL  Phenols are compounds in which the hydroxyl group is attached to a benzene ring.  Phenol is the simplest member of a family of compounds in which an -OH group is attached directly to a benzene ring. Structure Of Phenol O H Physical properties Pure phenol is a white crystalline solid, smelling of disinfectant. The crystals are often rather wet and discolored. Phenols have the formula Ar-OH Ar must be an aromatic ring (e.g., Benzene)
  11. 11. Widely used in healthcare as: Germicides Antiseptics Disinfectants Melting and boiling points high melting and boiling points ...DocumentsMr. BLITHEDocumentsmy filesmy academic files (2013-2014)MY chem reports (organic Chem)ACTUAL REPORTattachment.pptx Hydrogen bonds can form between a lone pair on an oxygen on one molecule and the hydrogen on the -OH group of one of its neighbors. Solubility in water Phenol is moderately soluble in water - about 8 g of phenol will dissolve in 100 g of water. Phenol is somewhat soluble in water because of its ability to form hydrogen bonds with the water.
  12. 12. ETHERS Ethers are a class of organic compounds characterized by an oxygen atom connected to two hydrocarbon groups. Ethers do not H-bond with themselves, so have boiling points similar to hydrocarbons Ethers are only slightly soluble in water and are highly flammable Structure of ETHERS  An ether is a characterized by an oxygen bonded to two alkyl or aryl groups, represented here by R and R'. The substituent's can be, but do not need to be, the same.
  13. 13. Ethers can act as a hydrogen-bond acceptor, as shown in the figure on the right. But, they can't act as hydrogen-bond donors. Solubility Less likely to be soluble in water than the alcohol with the same molecular weight. The absence of an -OH group in an ether also has important consequences for its chemical properties. Ethers are essentially inert to chemical reactions. They don't react with most oxidizing or reducing agents, and they are stable to most acids and bases, except at high temperatures. However, extremely FLAMMABLE explode if exposed to air for longer periods of time, to form EXPLOSIVE PEROXIDES.
  14. 14. Melting and Boiling points Boiling points and melting points are dictated by intermolecular forces. Compared with alkane of similar molar mass, an ether will have a similar boiling point. Compared to an alcohol of the same molar mass, the ether will have a much lower boiling point.
  15. 15. Medical use of Ethers Ethers are often used as anesthetics Accumulate in the lipid material of nerve cells interfering with nerve impulse transmission. Today halogenated ethers are used routinely as general anesthetics Less flammable Safer to store and to work with
  16. 16. Nomenclature
  17. 17. ALCOHOL Name the C-atoms of a single alkyl group as for alkanes. Add the word “alcohol” following a space after the alkyl name. 1) CH3--OH methyl alcohol For example: 2) CH3 CH2--OH ethyl alcohol COMMON NAME
  18. 18. IUPAC NAME
  19. 19. CH3CHCHCH3 OH CH3 For example: Butane Butanol 1234 3-methyl-2-butanol Try this one: 1. CH3-CH-CH2OH CH3 2-methyl-1-propanol
  20. 20. Alcohols with more than one OH group Polyhydroxyl alcohols possess more than one OH group. Alcohols which possess two OH groups are called “diols” and those with three OH groups are called “triols” Naming this kind of Compound is simple, just follow this: Alkane name + the number of the OH group For example: 1. CH2-CH-CH2 OHOH OH 1,2,3-propanetriol 1,2-Ethanediol 1,2-Propanediol 1,2,3-Propanetriol
  21. 21. Naming Alcohols…continuation 1. Name the parent compound. 2. Replace the –e with –ol. 3. Number the ring to minimize number of carbon with the –OH group 4. Identify, name, and number all substituent/s. OH CH3 For example: Six Carbon ring= Cyclohexane Cyclohexanol number counterclockwise  methyl on C-3 Note: OH must be at C-1 3-methylcyclohexanol
  22. 22. PHENOL Compounds with additional substituent's are named as substituted phenols when there is only one other substituent, Ortho, Meta or Para are used. Mono-substituted phenols are characterized using the prefix ortho (o-), meta (m-) or para (p-) depending on the placement of the substituent from the hydroxyl group. ortho: (1,2-) meta :(1,3-) para : (1,4-) Cl Cl Cl o-chlorophenol m-chlorophenol p-chlorophenol
  23. 23. If there are two or more additional substituent's, each must be numbered, beginning at the OH and going in direction that gives substituent's lowest numbers (or alphabetical if same in both directions). The simplest member of phenol is called phenol itself or hydroxybenzene and the rest are named as its derivatives. Phenol or Hydroxybenzene  Functional group suffix = -common - phenol, systematic - benzenol  Functional group prefix = hydroxy  di , tri and so forth are used to denote the number of substituent.
  24. 24. For example: OH 1,2-dihydroxybenzene OH 1,3-dihydroxybenzene CH3 3-methylphenol NO2 NO2 NO2 2,4,6- trinitrophenol NOTE: Many have common or trivial names that do not at all suggest the structure…
  25. 25. ETHERS Common Name For common names: name each alkyl group attached to the oxygen followed by ether. For example: 1. CH3-CH2-O-CH2-CH3 Diethyl Ether 2. CH3-CH2-O-CH3 Ethyl methyl Ether Methyl phenyl Ether
  26. 26. IUPAC NAME For complex ethers IUPAC names are used Step1: Name as an alkane, with larger alkyl group being the parent chain. Step 2: Find the smaller alkyl group and the O are named together as an alkoxy group (replace -yl with -oxy) e.g., CH3CH2O = ethoxy Step 3: Number chain starting at end nearest alkoxy group Step 4: Use a number to give location of alkoxy group For example: CH3CH2CH2CH2CH2-O-CH3 1-methoxypentane Pentane Methyl=Methoxy1
  27. 27. Try this one: 1. CH3-CH2-CH2---C---CH2-CH3 CH3 CH3 O 3-methoxy-3methylhexane
  28. 28. Naming Cyclic Ethers Cyclic ethers are generally named by their common names. A cyclic ether containing two carbons is called ethylene oxide (generally known as epoxides) A cyclic ether containing 4 carbons (with 2 double bonds) is called a furan A cyclic ether containing 5 carbons (with 2 double bonds) is called a pyran A cyclic ether containing 4 carbons and 2 oxygens is called a dioxane
  29. 29. TRIVIA… PHENOLS are next-generation anti-oxidant found throughout nature in some of the healthiest foods. PHENOLS are the common health-giving link that ties together foods, such as Red Wine, Green Tea, Dark Chocolate, and Super-Berries. In human health these compounds are thought to be instrumental in combating oxidative stress, a process associated with some neurodegenerative diseases and some cardiovascular diseases.
  30. 30. Approximately 600,000 students per year are assaulted by a drinking student. Research suggests that women are more vulnerable than men to many alcohol- induced problems. Some of these include, Organ Damage, Trauma, Legal and interpersonal difficulties. Alcohol affects men and women differently. Women become more impaired than men from drinking the same amount of alcohol. This is because women: • Are generally smaller in size • Have less body water • Have less dehydrogenase. • Have more estrogen Alcohol is a central nervous system depressant. In small amounts it can have a relaxing effect.
  31. 31. Thank You for LISTENING!!!