Finals

• • The functional group is an OH (hydroxyl) group bonded to an sp 3 hybridized carbon atom.
  • The oxygen atom of an alcohol is also sp 3 hybridized.
  • Two sp 3 hybrid orbitals of oxygen form sigma bonds to atoms of carbon and hydrogen.
  • The other two sp 3 hybrid orbitals of oxygen each contain an unshared pair of electrons.

  Alcohol
• what functional group is this

  Alcohol

  
• (T or F) Alcohols are classified as primary (1°), secondary (2°), or tertiary (3°), depend ing on the number of carbon substituents bonded

  to the hydroxyl-bearing carbon.

  True
• identify whether all the statements are right or wrong?

  a)The functional group is the center of reactivity in an organic molecule.

  b)The IUPAC system uses prefixes to denote certain

  functional groups.

  c)The functional group of an alcohol is the OH group,

  which is denoted by the suffix “ol.”

  d) all the statements are correct

  b.) uses suffixes
• The following rules are used to name a compound that has a functional group suffix: (which statement is wrong)

  a)The parent hydrocarbon is the longest continuous

  chain that contains the functional group.

  b) The parent hydrocarbon is numbered in the

  direction that gives the functional group suffix

  the highest possible number?

  b.) gives the functional group suffix the lowest possible number
• what is the name of alcohol this compound:

  2-butanol or butan-2-ol

  
• what is the name of alcohol this compound:

  2-ethyl-1-pentanol or 2-ethylpentan-1-ol

  
• what is the name of alcohol this compound:

  3-butoxy-1-propanol or 3-butoxypropan-1-ol

  
• ( T or F )If there are two OH groups, the suffix “triol” is added to the name of the parent hydrocarbon.

  False (the suffix “diol”)
• (T or F) If there is a functional group suffix and a substituent, the functional group suffix gets the lowest possible number.

  True
• (T or F) If counting in either direction gives the same number for the functional group suffix, then the chain is numbered in the direction that gives a substituent the highest possible number.

  False (gives a substituent the lowest possible number)
• ( T or F) If there is more than one substituent, the substituents are listed in alphabetical order.

  True
• (T or F) In IUPAC names for diols, triols, and so on, the final ‐e of the parent alkane name is retained, as for example, in 1,2‐ethanediol.

  True
• IUPAC naming of R-OH

  1. In IUPAC names for diols, triols, and so on, the final ‐e of the parent alkane name is retained, as for example, in 1,2‐ethanediol.

  2. The parent hydrocarbon is the longest continuous chain that contains the functional group.

  3. If there is more than one substituent, the substituents are listed in alphabetical order.

  4. The parent hydrocarbon is numbered in the direction that gives the functional group suffix the lowest possible number

  5. If there are two OH groups, the suffix "diol" is added to the name of the parent hydrocarbon.

  6. If there is a functional group suffix and a substituent, the functional group suffix gets the lowest possible number.

  7. If counting in either direction gives the same number for the functional group suffix, then the chain is numbered in the direction that gives a substituent the lowest possible number. Notice that a number is not needed to designate the position of a functional group suffix in a cyclic compound, because it is assumed to be at the 1 position
• Order of IUPAC naming

  • 2,4,5,6,7,3,1
  • 1,5,4,3,6,7,2
  • 2,4,5,1,3,7,6
  • 1,2,3,4,5,6,7
• Compounds containing two hydroxyl groups on different carbons are often referred to as ?

  Glycols
• We often refer to compounds containing OH and C=C groups as ?

  unsaturated alcohols
• arrange in correct order:

  1.Show the double bond by changing the infix of the parent alkane from ‐an‐ to ‐en, and show the alcohol by changing the suffix of the parent alkane from ‐e to ‐ol.

  2. Use numbers to show the location of both the carbon– carbon double bond and the hydroxyl group.

  3. Number the parent alkane so as to give the OH group the lowest possible number.

  a.)3,2,1

  b.)1,3,2

  c.)3,1,2

  d.)1,2,3

  c.) 3,1,2
• (T or F) The most important physical property of alcohols is the polarity of their OH groups. Because of the large difference in electronegativity, both the C-O and O-H bonds of an alcohol are polar covalent, and alcohols are polar molecules?

  True
• (T or F) Alcohols have higher boiling points than alkanes of similar molecular weight, because alcohols are polar molecules and can associate in the liquid state by a type of dipole–dipole intermolecular attraction called hydrogen bonding?

  True
• (T or F) Alcohols are much more soluble in water than are alkanes, alkenes, and alkynes of comparable molecular weight. Their increased solubility is due to hydrogen bonding between alcohol molecules and water. Methanol, ethanol, and 1‐propanol are soluble in water in all proportions?

  True
• ( T or F) aqueous solutions of alcohols have about the different pH as that of pure water.

  False (same pH as that of pure water)
• ( T or F) In the presence of strong acids, the oxygen

  atom of an alcohol is a strong base and reacts with an acid by proton transfer to form an oxonium ion

  False (the oxygen atom of an alcohol is a weak base)
• (T or F) alcohols react with Li, Na, Mg and other active metals to liberate hydrogen and to form metal alkoxides

  False ( Li, Na, K, Mg, and other active metalsLi, Na, K, Mg, and other active metals)
• ( T or F) Conversion to Haloalkanes The conversion of an alcohol to an alkyl halide involves substituting halogen for OH at a unsaturated carbon. The most common reagents for this conversion are the

  halogen acids and SOCl2.

  False ( involves substituting halogen for OH at a saturated carbon)
• ( T or F) Reaction with HCl, HBr, and HI Water‐soluble tertiary alcohols react very rapidly with HCl, HBr, and HI. Mixing a tertiary alcohol with concentrated

  hydrochloric acid for a few minutes at room temperature converts the alcohol to a water insoluble chloroalkane that separates from the aqueous layer.

  True
• ( T or F) Primary and secondary alcohols are converted to bromoalkanes and iodoalkanes by treatment with concentrated hydrobromic and hydroiodic acids.

  False ( un concentrated hydrobromic and hydroiodic acids)
• it is the most widely used reagent for the conversion of primary and secondary alcohols to alkyl chlorides.The by‐products of this nucleophilic substitution reaction are HCl and SO2.

  thionyl chloride, SOCl2.
• ( T or F) Elimination of a molecule of water from

  adjacent carbon atoms, an alcohol can be

  converted to an alkene.

  True
• (T or F) in reactions of alcohol:

  • Primary alcohol = aldehyde or a carboxylic acid
  • Secondary alcohols = ketones
  • Tertiary alcohols are oxidized

  Tertiary alcohols are not oxidized
• name this compound:

  aldehyde

  
• name this compound:

  Carboxylic acid

  
• name this compound:

  2-Isopropyl-5-methyl-cyclohexanol (Menthol)

  
• name this compound:

  2-Isopropyl-5-methyl-cyclohexanone (Menthone)

  
• This functional group of an atom of oxygen bonded to two carbon atoms that are part of a hydrocarbon chain or ring.

  Ether
• It is the simplest ether;two sp 3 hybrid orbitals of

  oxygen form sigma bonds to carbon atoms

  Dimethyl ether
• the two alkyl groups are the same (R and R)

  symmetrical ether
• the two alkyl groups are different (R and R′)

  unsymmetrical ether
• • It is same with alcohol
  • In the IUPAC system, they are named by selecting the longest carbon chain as the parent alkane and naming the OR group bonded to it as an alkoxy (alkyl + oxygen) group.
  • Common names are derived by listing the alkyl groups bonded to oxygen in alphabetical order and adding the word ether.

  Ether
• (T or F)The IUPAC system names an ether as an alkane with an RO substituent. The substituents are named by replacing the “yl” ending in the name of the alkyl substituent with “oxy.”

  True