12 alcohols-phenols-thiols-ethers

Eastern Kentucky University
Eastern Kentucky UniversityAdjunct Professor um Eastern Kentucky University
Chapter 12



Alcohols, Phenols, Thiols, and Ethers



                                        1
1. Alcohols: structure and properties

The functional group found on all alcohols is the hydroxyl
group, -OH.
Alcohols are like water molecules, but with an alkyl group
(-R) substituted for one of the hydrogens.




            H-OH                   R-OH


                                                         2
1. Alcohols: structure and properties

Since oxygen is more
electronegative than carbon
and hydrogen, the hydroxyl
group makes alcohol molecules
polar.

This polarity, along with the
hydrogen bonded to oxygen,
allows alcohols to hydrogen-
bond.

                                               3
1. Alcohols: structure and properties




                                        4
1. Alcohols: structure and properties

The strength of hydrogen-bonding causes alcohols to
have higher melting and boiling points than the
corresponding hydrocarbons.

   Compound          Molar Mass       Boiling Point
   CH3CH2CH3          44 g/mol           -42 oC
    CH3CH2OH          46 g/mol          +78.5 oC
  CH3CH2CH2CH3        58 g/mol           -0.5 oC
  CH3CH2CH2OH         60 g/mol           97.2 oC


                                                      5
1. Alcohols: structure and properties

Small alcohol molecules (1-4 carbons) are very soluble in
water.

Alcohols with 5-6 carbons are moderately soluble in
water.

Larger alcohols are not appreciably soluble in water.



                         WHY?
                                                            6
1. Alcohols: structure and properties

Name        Formula           Water solubility*
methanol    CH3OH               miscible
ethanol     C2H5OH              miscible
propanol    C3H7OH              miscible
butanol     C4H9OH                0.11
pentanol    C5H11OH              0.030
hexanol     C6H13OH              0.0058
heptanol    C7H15OH              0.0008

                  *mol/100g at 25oC

                                                  7
1. Alcohols: structure and properties

The hydroxyl end of an alcohol molecule is hydrophilic.
  “Water-loving”

The nonpolar hydrocarbon portion of the alcohol
molecule is hydrophobic.
  “Water-fearing”

As the nonpolar portion becomes larger relative to the
polar portion, water solubility decreases.



                                                          8
1. Alcohols: structure and properties

  The presence of multiple hydroxyl groups on a carbon
  chain will increase solubility.

Name              Formula              Water solubility*

butanol                                     0.11

1,4-butanediol                            miscible



                                            Tegrity lecture video

                                                                    9
1. Alcohols: structure and properties




                                        10
1. Alcohols: structure and properties

  Here’s Journal question number one!

tag = alcohols
  What characteristic of alcohols is responsible for both
  their high boiling points and their high degree of
  solubility in water? How does this characteristic cause
  high boiling points and high solubilities?




                                                            11
2. Alcohols: Nomenclature


1) Name the parent compound based on the longest
   carbon chain or the carbon ring.
2) Replace the parent name ending –e with –ol.
3) Number the parent chain to give the hydroxyl carbon
   the lowest possible number.
4) Identify, name, and number all additional substituents.



                                                             12
2. Alcohols: Nomenclature

1) Name the parent compound based on
    the longest carbon chain or the carbon
    ring.
                   butane
2) Replace the parent name ending –e with
    –ol.
                  butanol
3) Number the parent chain to give the
    hydroxyl carbon the lowest possible
    number.
                 2-butanol
4) Identify, name, and number all
    additional substituents.
          3-methyl-2-butanol
                                             13
2. Alcohols: Nomenclature

Name the following compounds:



                       pencast




                                  14
2. Alcohols: Nomenclature

Draw structures for the following compounds:
  2-methyl-1-propanol

  2-chlorocyclopentanol          pencast




  2,4-dimethylcyclohexanol

  2,3-dichloro-3-hexanol

  1,2,3-pentanetriol


                                               15
4. Classification of alcohols

In an alcohol, the carbon atom with the hydroxyl group (-
OH) attached to it is called the              .




What distinguishes the four carbinol carbons above?
                                                        16
4. Classification of alcohols

Methanol is in a class by itself, with 0 carbons/3
hydrogens attached to the carbinol carbon.
Primary (1o) alcohols have 1 carbon/2 hydrogens
attached to the carbinol carbon.
  ethanol
Secondary (2o) alcohols have 2 carbons/1 hydrogen
attached to the carbinol carbon.
  2-propanol
Tertiary (3o) alcohols have 3 carbons/0 hydrogens
attached to the carbinol carbon.
  2-methyl-2-propanol
                                                     17
4. Classification of alcohols

Methanol

(1o)



(2o)



(3o)

                                       18
4. Classification of alcohols

   Alcohols often react differently depending on their
   classification as 1o, 2o, or 3o.

   A fourth classification is aromatic alcohol, with the
   hydroxyl group attached to a carbon on an aromatic ring.

        The simplest of these is phenol.




Tegrity lecture video                                         19
4. Classification of alcohols

Name each alcohol and classify it as 1o, 2o, or 3o.




                              pencast




                                                      20
5. Reactions involving alcohols

Preparation of alcohols: hydration of an alkene
  See slides 39-42 of the Chapter 11 powerpoint.
  Remember that Markovnikov’s rule applies.




                                                   21
5. Reactions involving alcohols

Preparation of alcohols: hydrogenation of aldehydes
and ketones.
  Addition of H2 to a double bond (C=O)
  These reactions are also called reductions (fewer C-O bonds,
  more C-H bonds)

                 catalyst




                                            catalyst




                                                                 22
5. Reactions involving alcohols

Write a balanced equation for the hydrogenation of
ethanal (two-carbon aldehyde).




Name the product.                             pencast




                                                        23
5. Reactions involving alcohols

Write a balanced equation for the hydrogenation of 2-
hexanone (six-carbon ketone).




                             pencast




Name the product.

                                                        24
5. Reactions involving alcohols

Dehydration of alcohols
  Dehydration is the reverse of hydration.
  Dehydration is a type of elimination reaction.
  In the presence of heat and a strong acid, -OH and –H are
  removed from adjacent carbon atoms.
  A double bond is formed between these atoms.




                                                              25
5. Reactions involving alcohols

Sometimes, more than one product of dehydration is
possible.




                      major product      minor product
  2-butanol             2-butene           1-butene



Zaitsev’s rule: In an elimination reaction, the more
highly substituted product alkene will be the major
product.
                                                         26
5. Reactions involving alcohols

Give the product(s) of dehydration of the following
alcohol. Name the reactant and the product(s).

        pencast




                                                      27
5. Reactions involving alcohols

Give the product(s) of dehydration of the following
alcohol. Name the reactant and the product(s).




                                                  pencast




                                                            28
5. Reactions involving alcohols



Give the product(s) of
dehydration of this
alcohol. Name the
reactant and the
product(s).                       pencast




                                            29
5. Reactions involving alcohols

Oxidation reactions in organic chemistry
  Oxidation is a gain of a bond to oxygen and loss of a bond to
  hydrogen.
  Reduction is the flip side of oxidation—loss of a bond to oxygen
  and gain of a bond to hydrogen.
An oxidizing agent causes oxidation to take place and is
itself reduced.
  basic potassium permanganate (KMnO4/OH-)
  chromic acid (H2CrO4)
  general symbol [O] over the reaction arrow


                                                                 30
5. Reactions involving alcohols

  Oxidation reactions in organic chemistry




Tegrity lecture video                             31
5. Reactions involving alcohols

  Here’s Journal question #2.
Tag = oxidation
  Combustion of an alkane to produce carbon dioxide (and
  water) is an oxidation reaction. Now that you know
  oxidation involves forming more bonds to oxygen and
  fewer bonds to hydrogen, give the [hypothetical] steps in
  the combustion (that is, oxidation) of methane to carbon
  dioxide. Each step should produce a molecule with one
  more carbon-oxygen bond and one less carbon-hydrogen
  bond. Name the molecule produced in each step, ending
  with carbon dioxide. There are four steps and four
  product molecules if you include carbon dioxide.
                                                          32
5. Reactions involving alcohols




                         WHY?


                                  33
5. Reactions involving alcohols




                             Tegrity lecture video   34
5. Reactions involving alcohols

Draw the product of oxidation of the following alcohols
and name the product.
  propanol
                                 pencast
  cyclohexanol
  2-methyl-2-hexanol
  1-methyl-1-cyclopentanol
  3-phenyl-1-propanol
                                             pencast



How can acetone be prepared from propene?


                                                          35
5. Reactions involving alcohols

When ethanol is metabolized in the liver in the following
series of reactions, catalyzed by liver enzymes.




What causes a hangover?
                    Step 2 of oxidation




                                                            36
6. Oxidation and reduction in living systems

In inorganic reactions, oxidation and reduction are often
accompanied by changes in charge and transfer of
electrons.
  Oxidation of sodium: Na  Na+ + e-
  Reduction of chlorine: Cl + e-  Cl-


In organic systems, there are normally no changes in
charge or obvious transfers of electrons.
  Oxidation: more bonds to oxygen or fewer bonds to hydrogen
  Reduction: fewer bonds to oxygen or more bonds to hydrogen


                                                               37
6. Oxidation and reduction in living systems


                   more oxidized form




alkane          alcohol         aldehyde   carboxylic acid


                    more reduced form



                                                             38
7. Phenols

Compounds with a hydroxyl group attached to a benzene
ring are called phenols.




As with alcohols, the hydroxyl group makes the
compound polar and can participate in hydrogen
bonding.
Smaller phenols are slightly soluble in water.
                                                    39
7. Phenols

The compound phenol
  is a solid at room temperatures;
  is colorless and poisonous;
  has a penetrating odor;
  turns red when exposed to air.


The acid-base indicator
phenolphthalein
  has two phenolic hydroxyl groups;
  is colorless in acidic solution;
  is deep magenta in basic solution.
                                       40
8. Ethers

Ethers are similar to alcohols, but the –H of the hydroxyl
group is replaced by another –R group.

 alcohol                                   ether



Intermolecular forces are weaker in ethers than in
alcohols because the absence of an O-H bond precludes
hydrogen bonding.
Ethers are slightly polar due to the C-O bonds.


                                                             41
8. Ethers

Boiling points of ethers are
  higher than for the corresponding alkanes.
  much lower than for the corresponding alcohols.




                                             Tegrity lecture video   42
8. Naming ethers

The IUPAC names for ethers are based on the alkane
name of the longest chain attached to the oxygen.
The shorter chain is named as an alkoxy substituent, an
alkane with the -ane replaced by –oxy.
           CH3CH2CH2CH2CH2-O-CH3
                  1-methoxypentane

Give the IUPAC names for the ethers on the next slide.



                                                          43
8. Naming ethers

Give the IUPAC names for the following ethers.




         pencast




                                                 44
8. Synthesis of ethers

A dehydration (removal of water) reaction between two
alcohols will produce an ether.




Heat and the presence of hydrogen ions are necessary for
the reaction to take place.



   ethanol   +   ethanol      ethoxyethane   +   water

                                                          45
8. Synthesis of ethers

If two different alcohols undergo a dehydration, a
mixture of products is possible.
                                       methoxyethane



    ethanol   +   methanol
                                       methoxymethane




                                        ethoxyethane




                                                        46
8. Synthesis of ethers

  And finally, Journal question #3.

Tag = solubility

  Compare the relative solubilities in water of alkanes,
  alcohols, phenols, and ethers. Explain their relative
  solubilities in terms of their differing molecular structures
  and their intermolecular forces with water molecules.



                                                              47
9. Thiols

The sulfhydryl group, -SH, is analogous
to the hydroxyl group, -OH.

A compound with a sulfhydryl group is
called a thiol.

Thiols are named by adding the suffix
thiol to the name of the parent
compound.


                                          48
9. Thiols

Name the following compounds:

                       pencast




                                 49
9. Thiols

Draw structures for the following compounds:

  1,3-butanedithiol

  2-methyl-2-pentanethiol
                                      pencast
  2-chloro-2-propanethiol

  cyclopentanethiol



                                                50
9. Thiols

Two thiols can be oxidized (lose hydrogen) to form a
disulfide.


                                         +   2 H+ + 2 e-



Disulfide bonds are important for the structure and
shape of many proteins. (more about this in Module 8)



                                                           51
9. Thiols




            52
9. Thiols

Synthesis of insulin
  Disulfide bonds form to shape preproinsulin.
  Loss of the gray portion of the chain forms insulin .




                                                          53
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12 alcohols-phenols-thiols-ethers

  • 1. Chapter 12 Alcohols, Phenols, Thiols, and Ethers 1
  • 2. 1. Alcohols: structure and properties The functional group found on all alcohols is the hydroxyl group, -OH. Alcohols are like water molecules, but with an alkyl group (-R) substituted for one of the hydrogens. H-OH R-OH 2
  • 3. 1. Alcohols: structure and properties Since oxygen is more electronegative than carbon and hydrogen, the hydroxyl group makes alcohol molecules polar. This polarity, along with the hydrogen bonded to oxygen, allows alcohols to hydrogen- bond. 3
  • 4. 1. Alcohols: structure and properties 4
  • 5. 1. Alcohols: structure and properties The strength of hydrogen-bonding causes alcohols to have higher melting and boiling points than the corresponding hydrocarbons. Compound Molar Mass Boiling Point CH3CH2CH3 44 g/mol -42 oC CH3CH2OH 46 g/mol +78.5 oC CH3CH2CH2CH3 58 g/mol -0.5 oC CH3CH2CH2OH 60 g/mol 97.2 oC 5
  • 6. 1. Alcohols: structure and properties Small alcohol molecules (1-4 carbons) are very soluble in water. Alcohols with 5-6 carbons are moderately soluble in water. Larger alcohols are not appreciably soluble in water. WHY? 6
  • 7. 1. Alcohols: structure and properties Name Formula Water solubility* methanol CH3OH miscible ethanol C2H5OH miscible propanol C3H7OH miscible butanol C4H9OH 0.11 pentanol C5H11OH 0.030 hexanol C6H13OH 0.0058 heptanol C7H15OH 0.0008 *mol/100g at 25oC 7
  • 8. 1. Alcohols: structure and properties The hydroxyl end of an alcohol molecule is hydrophilic. “Water-loving” The nonpolar hydrocarbon portion of the alcohol molecule is hydrophobic. “Water-fearing” As the nonpolar portion becomes larger relative to the polar portion, water solubility decreases. 8
  • 9. 1. Alcohols: structure and properties The presence of multiple hydroxyl groups on a carbon chain will increase solubility. Name Formula Water solubility* butanol 0.11 1,4-butanediol miscible Tegrity lecture video 9
  • 10. 1. Alcohols: structure and properties 10
  • 11. 1. Alcohols: structure and properties Here’s Journal question number one! tag = alcohols What characteristic of alcohols is responsible for both their high boiling points and their high degree of solubility in water? How does this characteristic cause high boiling points and high solubilities? 11
  • 12. 2. Alcohols: Nomenclature 1) Name the parent compound based on the longest carbon chain or the carbon ring. 2) Replace the parent name ending –e with –ol. 3) Number the parent chain to give the hydroxyl carbon the lowest possible number. 4) Identify, name, and number all additional substituents. 12
  • 13. 2. Alcohols: Nomenclature 1) Name the parent compound based on the longest carbon chain or the carbon ring. butane 2) Replace the parent name ending –e with –ol. butanol 3) Number the parent chain to give the hydroxyl carbon the lowest possible number. 2-butanol 4) Identify, name, and number all additional substituents. 3-methyl-2-butanol 13
  • 14. 2. Alcohols: Nomenclature Name the following compounds: pencast 14
  • 15. 2. Alcohols: Nomenclature Draw structures for the following compounds: 2-methyl-1-propanol 2-chlorocyclopentanol pencast 2,4-dimethylcyclohexanol 2,3-dichloro-3-hexanol 1,2,3-pentanetriol 15
  • 16. 4. Classification of alcohols In an alcohol, the carbon atom with the hydroxyl group (- OH) attached to it is called the . What distinguishes the four carbinol carbons above? 16
  • 17. 4. Classification of alcohols Methanol is in a class by itself, with 0 carbons/3 hydrogens attached to the carbinol carbon. Primary (1o) alcohols have 1 carbon/2 hydrogens attached to the carbinol carbon. ethanol Secondary (2o) alcohols have 2 carbons/1 hydrogen attached to the carbinol carbon. 2-propanol Tertiary (3o) alcohols have 3 carbons/0 hydrogens attached to the carbinol carbon. 2-methyl-2-propanol 17
  • 18. 4. Classification of alcohols Methanol (1o) (2o) (3o) 18
  • 19. 4. Classification of alcohols Alcohols often react differently depending on their classification as 1o, 2o, or 3o. A fourth classification is aromatic alcohol, with the hydroxyl group attached to a carbon on an aromatic ring. The simplest of these is phenol. Tegrity lecture video 19
  • 20. 4. Classification of alcohols Name each alcohol and classify it as 1o, 2o, or 3o. pencast 20
  • 21. 5. Reactions involving alcohols Preparation of alcohols: hydration of an alkene See slides 39-42 of the Chapter 11 powerpoint. Remember that Markovnikov’s rule applies. 21
  • 22. 5. Reactions involving alcohols Preparation of alcohols: hydrogenation of aldehydes and ketones. Addition of H2 to a double bond (C=O) These reactions are also called reductions (fewer C-O bonds, more C-H bonds) catalyst catalyst 22
  • 23. 5. Reactions involving alcohols Write a balanced equation for the hydrogenation of ethanal (two-carbon aldehyde). Name the product. pencast 23
  • 24. 5. Reactions involving alcohols Write a balanced equation for the hydrogenation of 2- hexanone (six-carbon ketone). pencast Name the product. 24
  • 25. 5. Reactions involving alcohols Dehydration of alcohols Dehydration is the reverse of hydration. Dehydration is a type of elimination reaction. In the presence of heat and a strong acid, -OH and –H are removed from adjacent carbon atoms. A double bond is formed between these atoms. 25
  • 26. 5. Reactions involving alcohols Sometimes, more than one product of dehydration is possible. major product minor product 2-butanol 2-butene 1-butene Zaitsev’s rule: In an elimination reaction, the more highly substituted product alkene will be the major product. 26
  • 27. 5. Reactions involving alcohols Give the product(s) of dehydration of the following alcohol. Name the reactant and the product(s). pencast 27
  • 28. 5. Reactions involving alcohols Give the product(s) of dehydration of the following alcohol. Name the reactant and the product(s). pencast 28
  • 29. 5. Reactions involving alcohols Give the product(s) of dehydration of this alcohol. Name the reactant and the product(s). pencast 29
  • 30. 5. Reactions involving alcohols Oxidation reactions in organic chemistry Oxidation is a gain of a bond to oxygen and loss of a bond to hydrogen. Reduction is the flip side of oxidation—loss of a bond to oxygen and gain of a bond to hydrogen. An oxidizing agent causes oxidation to take place and is itself reduced. basic potassium permanganate (KMnO4/OH-) chromic acid (H2CrO4) general symbol [O] over the reaction arrow 30
  • 31. 5. Reactions involving alcohols Oxidation reactions in organic chemistry Tegrity lecture video 31
  • 32. 5. Reactions involving alcohols Here’s Journal question #2. Tag = oxidation Combustion of an alkane to produce carbon dioxide (and water) is an oxidation reaction. Now that you know oxidation involves forming more bonds to oxygen and fewer bonds to hydrogen, give the [hypothetical] steps in the combustion (that is, oxidation) of methane to carbon dioxide. Each step should produce a molecule with one more carbon-oxygen bond and one less carbon-hydrogen bond. Name the molecule produced in each step, ending with carbon dioxide. There are four steps and four product molecules if you include carbon dioxide. 32
  • 33. 5. Reactions involving alcohols WHY? 33
  • 34. 5. Reactions involving alcohols Tegrity lecture video 34
  • 35. 5. Reactions involving alcohols Draw the product of oxidation of the following alcohols and name the product. propanol pencast cyclohexanol 2-methyl-2-hexanol 1-methyl-1-cyclopentanol 3-phenyl-1-propanol pencast How can acetone be prepared from propene? 35
  • 36. 5. Reactions involving alcohols When ethanol is metabolized in the liver in the following series of reactions, catalyzed by liver enzymes. What causes a hangover? Step 2 of oxidation 36
  • 37. 6. Oxidation and reduction in living systems In inorganic reactions, oxidation and reduction are often accompanied by changes in charge and transfer of electrons. Oxidation of sodium: Na  Na+ + e- Reduction of chlorine: Cl + e-  Cl- In organic systems, there are normally no changes in charge or obvious transfers of electrons. Oxidation: more bonds to oxygen or fewer bonds to hydrogen Reduction: fewer bonds to oxygen or more bonds to hydrogen 37
  • 38. 6. Oxidation and reduction in living systems more oxidized form alkane alcohol aldehyde carboxylic acid more reduced form 38
  • 39. 7. Phenols Compounds with a hydroxyl group attached to a benzene ring are called phenols. As with alcohols, the hydroxyl group makes the compound polar and can participate in hydrogen bonding. Smaller phenols are slightly soluble in water. 39
  • 40. 7. Phenols The compound phenol is a solid at room temperatures; is colorless and poisonous; has a penetrating odor; turns red when exposed to air. The acid-base indicator phenolphthalein has two phenolic hydroxyl groups; is colorless in acidic solution; is deep magenta in basic solution. 40
  • 41. 8. Ethers Ethers are similar to alcohols, but the –H of the hydroxyl group is replaced by another –R group. alcohol ether Intermolecular forces are weaker in ethers than in alcohols because the absence of an O-H bond precludes hydrogen bonding. Ethers are slightly polar due to the C-O bonds. 41
  • 42. 8. Ethers Boiling points of ethers are higher than for the corresponding alkanes. much lower than for the corresponding alcohols. Tegrity lecture video 42
  • 43. 8. Naming ethers The IUPAC names for ethers are based on the alkane name of the longest chain attached to the oxygen. The shorter chain is named as an alkoxy substituent, an alkane with the -ane replaced by –oxy. CH3CH2CH2CH2CH2-O-CH3 1-methoxypentane Give the IUPAC names for the ethers on the next slide. 43
  • 44. 8. Naming ethers Give the IUPAC names for the following ethers. pencast 44
  • 45. 8. Synthesis of ethers A dehydration (removal of water) reaction between two alcohols will produce an ether. Heat and the presence of hydrogen ions are necessary for the reaction to take place. ethanol + ethanol  ethoxyethane + water 45
  • 46. 8. Synthesis of ethers If two different alcohols undergo a dehydration, a mixture of products is possible. methoxyethane ethanol + methanol methoxymethane ethoxyethane 46
  • 47. 8. Synthesis of ethers And finally, Journal question #3. Tag = solubility Compare the relative solubilities in water of alkanes, alcohols, phenols, and ethers. Explain their relative solubilities in terms of their differing molecular structures and their intermolecular forces with water molecules. 47
  • 48. 9. Thiols The sulfhydryl group, -SH, is analogous to the hydroxyl group, -OH. A compound with a sulfhydryl group is called a thiol. Thiols are named by adding the suffix thiol to the name of the parent compound. 48
  • 49. 9. Thiols Name the following compounds: pencast 49
  • 50. 9. Thiols Draw structures for the following compounds: 1,3-butanedithiol 2-methyl-2-pentanethiol pencast 2-chloro-2-propanethiol cyclopentanethiol 50
  • 51. 9. Thiols Two thiols can be oxidized (lose hydrogen) to form a disulfide. + 2 H+ + 2 e- Disulfide bonds are important for the structure and shape of many proteins. (more about this in Module 8) 51
  • 52. 9. Thiols 52
  • 53. 9. Thiols Synthesis of insulin Disulfide bonds form to shape preproinsulin. Loss of the gray portion of the chain forms insulin . 53

Hinweis der Redaktion

  1. Note that propane and ethanol have nearly the same molar mass, but their melting points differ by 120 degrees C.Butane and propanol also have nearly the same molar mass, and their boiling points vary by almost 97 degrees C.This is dramatic experimental evidence of the effect of polarity and hydrogen bonding on the strength of intermolecular forces.
  2. The term “miscible” means that two substances will form a mixture in any proportion. So, for instance, 50 mL of water plus 50 mL of ethanol will form a mixture. But 1 mL of ethanol will mix with 99 mL of water just as well as 1 mL of water will mix with 99 mL of ethanol.Solubility is the maximum amount of a solute that can be dissolved in a given amount of solvent. In this case, solubility is expressed in units of moles solute per 100 grams water.
  3. Note that the ratio of carbons to hydroxyl groups is 2:1 for the 1,4-butanediol, the same as the ratio for ethanol. And both ethanol and 1,4-butanediol are completely miscible with water.
  4. ethanol
  5. 2-hexanol
  6. 4-methyl-3-hexanol is the reactant.The two products are 2-hexene and 3-hexene. 3-hexene is more highly substituted and is the major product.
  7. The reactant is 2-methyl-2-propanol.There is only one product because the molecule is symmetric around the carbon attached to the hydroxyl group.The product is 2-methyl-1-propene.
  8. The reactant is 2-methylcyclohexanol.The two products are 1-methylcyclohexene and 3-methylcyclohexene.Since 1-methylcyclohexene has the more highly substituted double bond, it is the major product.
  9. Oxidation requires that a second oxygen-carbon bond be formed to the carbinol carbon. In the case of primary and secondary alcohols, there is a hydrogen also attached to the carbinol carbon, and its loss allows the carbinol carbon to form another bond to oxygen. [Remember, carbon can only form four bonds!] For a tertiary alcohol, there are only alkyl groups attached to the carbinol carbon (no hydrogens) in addition to the hydroxyl group. The only way another carbon-oxygen bond could form would be if one of the alkyl groups left the carbinol carbon. And this would no longer be an oxidation reaction, because the ending product(s) would be different from the initial alcohol in other ways besides just having one more oxygen-carbon bond.
  10. Preparation of acetone:Hydration: Add water across the double bond. According to Markovnikov’s rule, the OH will be on carbon 2.Oxidation: Adding an oxidizing agent to the alcohol makes it into a ketone (C-O changed to C=O).
  11. 1-ethoxypropane1-methoxypropane1-ethoxybutane1-propoxybutane
  12. 1,2-propanedithiol benzenethiol 2-pentanethiol