1. Organic Chemistry Second Edition Chapter 13 David Klein
Alcohols and Phenols
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Klein, Organic Chemistry 2e

2. 13.1 Alcohols and Phenols Alcohols possess a hydroxyl group (-OH)
Hydroxyl groups are extremely common in natural compounds
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Klein, Organic Chemistry 2e

3. 13.1 Alcohols and Phenols Hydroxyl groups in natural compounds
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4. 13.1 Alcohols and Phenols
Phenols possess a hydroxyl group directly attached to an aromatic ring
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5. 13.1 Alcohols Nomenclature
Alcohols are named using the same procedure we used in Chapter 4 to name alkanes with minor modifications
Identify the parent chain, which should include the carbon that the –OH is attached to
Identify and Name the substituents
Assign a locant (and prefix if necessary) to each substituent. Give the carbon that the –OH is attached to the lowest number possible
List the numbered substituents before the parent name in alphabetical order. Ignore prefixes (except iso) when ordering alphabetically
The –OH locant is placed either just before
the parent name or just before the -ol suffix
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6. 13.1 Alcohols Nomenclature
Alcohols are named using the same procedure we used in Chapter 4 to name alkanes with minor modifications
Identify the parent chain
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7. 13.1 Alcohols Nomenclature
Alcohols are named using the same procedure we used in Chapter 4 to name alkanes with minor modifications
Assign a locant (and prefix if necessary) to each substituent. Give the carbon that the –OH is attached to the lowest number possible taking precedence over C=C double bonds
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8. 13.1 Alcohols Nomenclature
Alcohols are named using the same procedure we used in Chapter 4 to name alkanes with minor modifications
The –OH locant is placed either just before the parent name or just before the -ol suffix
R or S configurations should be shown at the beginning of the name
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9. 13.1 Alcohols Nomenclature
For cyclic alcohols, the –OH group should be on carbon 1, so often the locant is assumed and omitted
Common names for some alcohols are also frequently used
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10. 13.1 Alcohols Nomenclature
Like halides, alcohols are often classified by the type of carbon they are attached to
WHY do we use these classifications?
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11. 13.1 Alcohols Nomenclature
When an –OH group is attached to a benzene ring, the parent name is phenol
Practice with SkillBuilder 13.1
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12. 13.1 Alcohols Nomenclature
Name the following molecule
Draw the most stable chair conformation for (cis)-1-isopropyl-1,2-cyclohexanediol
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13. 13.1 Commercially Important Alcohols
Methanol (CH3OH) is the simplest alcohol
With a suitable catalyst, about 2 billion gallons of methanol is made industrially from CO2 and H2 every year
Methanol is poisonous, but it has many uses
Solvent
Precursor for chemical syntheses
Fuel
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14. 13.1 Commercially Important Alcohols
Ethanol (CH3CH2OH) has been produced by fermentation for thousands of years. HOW?
About 5 billion gallons of ethanol is made industrially from the acid-catalyzed hydration of ethylene every year
Ethanol has many uses
Solvent, precursor for chemical syntheses, fuel
Human consumption – ethanol suitable for drinking is heavily taxed. Ethanol used for purposes other than drinking is often denatured. WHY?
Is it poisonous?
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15. 13.1 Commercially Important Alcohols
Isopropanol is rubbing alcohol. Draw its structure
Isopropanol is made industrially from the acid-catalyzed hydration of propylene
Isopropanol is poisonous, but it has many uses
Industrial solvent
Antiseptic
Gasoline additive
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16. 13.1 Physical Properties of Alcohols
The –OH of an alcohol can have a big effect on its physical properties
Compare the boiling points below
Explain the differences
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17. 13.1 Physical Properties of Alcohols
Because they can H-bond, hydroxyl groups can attract water molecules strongly
Alcohols with small carbon chains are miscible in water (they mix in any ratio). WHY?
Alcohols with large carbon chains do not readily mix with water
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18. 13.1 Physical Properties of Alcohols
Do hydrophobic groups repel or attract water?
WHY are molecules with large hydrophobic groups generally insoluble in water?
Alcohols with 3 or less carbons are generally water miscible
Alcohols with more than 3 carbons are not miscible, and their solubility decreases as the size of the hydrophobic group increases
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19. 13.1 Physical Properties of Alcohols
An alcohol’s potency as an anti-bacterial agent depends on the size of the hydrophobic group
To kill a bacterium, the alcohol should have some water solubility. WHY?
To kill a bacterium, the alcohol should have a significant hydrophobic region. WHY?
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20. 13.1 Physical Properties of Alcohols
Hexylresorcinol is used as an antibacterial and as an antifungal agent
It has a good combination of hydrophobic and hydrophilic regions
It has significant water solubility
Its nonpolar region helps it to pass through cell membranes
Practice with conceptual checkpoint 13.3
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21. 13.2 Acidity of Alcohols and Phenols
A strong base is usually necessary to deprotonate an alcohol
A preferred choice to create an alkoxide is to treat the alcohol with Na, K, or Li metal. Show the mechanism for such a reaction
Practice with conceptual checkpoint 13.4
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22. 13.2 Acidity of Alcohols and Phenols
Recall from chapter 3 how ARIO is used to qualitatively assess the strength of an acid
Lets apply these factors to alcohols and phenols
Atom
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23. 13.2 Acidity of Alcohols and Phenols
Lets apply these factors to alcohols and phenols
Resonance
Explain why phenol is 100 million times more acidic than cyclohexanol
Show all relevant resonance contributors
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24. 13.2 Acidity of Alcohols and Phenols
Given the relatively low pKa of phenols, will NaOH be a strong enough base to deprotonate a phenol?
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25. 13.2 Acidity of Alcohols and Phenols
Lets apply these factors to alcohols and phenols
Induction: unless there is an electronegative group nearby, induction won’t be very significant
Orbital: in what type of orbital do the alkoxide electrons reside? How does that effect acidity?
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26. 13.2 Acidity of Alcohols and Phenols
Solvation is also an important factor that affects acidity
Water is generally used as the solvent when measuring pKa values
Which of the alcohols below is stronger?
ARIO cannot be used to explain the difference
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27. 13.2 Acidity of Alcohols and Phenols
Solvation explains the difference in acidity
Draw partial charges on the solvent molecules to show how solvation is a stabilizing effect
Practice with SkillBuilder 13.2
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Klein, Organic Chemistry 2e

28. 13.2 Acidity of Alcohols and Phenols
Use ARIO and solvation to rank the following molecules in order of increasing pKa
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29. 13.3 Preparation of Alcohols
We saw in chapter 7 that substitution reactions can yield an alcohol
What reagents did we use to accomplish this transformation?
We saw that the substitution can occur by SN1 or SN2
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30. 13.3 Preparation of Alcohols
The SN1 process generally uses a weak nucleophile (H2O), which makes the process relatively slow
Why isn’t a stronger nucleophile (-OH) used under SN1 conditions?
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31. 13.3 Preparation of Alcohols
In chapter 9, we learned how to make alcohols from alkenes
Recall that acid-catalyzed hydration proceeds through a carbocation intermediate that can possibly rearrange
How do you avoid rearrangements?
Practice with checkpoints 13.7 and 13.8
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32. 13.4 Alcohol Prep via Reduction
A third method to prepare alcohols is by the reduction of a carbonyl. What is a carbonyl?
Reductions involve a change in oxidation state
Oxidation state are a method of electron bookkeeping
Recall how we used formal charge as a method of electron bookkeeping
Each atom is assigned half of the electrons it is sharing with another atom
What is the formal charge on carbon in methanol?
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33. 13.4 Alcohol Prep via Reduction
For oxidation states, we imagine the bonds breaking heterolytically, and the electrons go to the more electronegative atom
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34. 13.4 Alcohol Prep via Reduction
Each of the carbons below have zero formal charge, but they have different oxidation states
Calculate the oxidation number for each
Is the conversion from formic acid  carbon dioxide an oxidation or a reduction?
What about formaldehyde  methanol?
Practice with SkillBuilder 13.3
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Klein, Organic Chemistry 2e

35. 13.4 Alcohol Prep via Reduction
The reduction of a carbonyl requires a reducing agent
Is the reducing agent oxidized or reduced?
If you were to design a reducing agent, what element(s) would be necessary?
Would an acid such as HCl be an appropriate reducing agent? WHY or WHY NOT?
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36. 13.4 Alcohol Prep via Reduction
There are three reducing agents you should know
We have already seen how catalyzed hydrogenation can reduce alkenes. It can also work for carbonyls
Forceful conditions (high temperature and/or high pressure)
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37. 13.4 Alcohol Prep via Reduction
Reagents that can donate a hydride are generally good reducing agents
Sodium borohydride
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38. 13.4 Alcohol Prep via Reduction
Reagents that can donate a hydride are generally good reducing agents
Lithium aluminum hydride (LAH)
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39. 13.4 Alcohol Prep via Reduction
Note that LAH is significantly more reactive that NaBH4
LAH reacts violently with water. WHY?
How can LAH be used with water if it reacts with water?
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40. 13.4 Alcohol Prep via Reduction
Hydride delivery agents will somewhat selectively reduce carbonyl compounds
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41. 13.4 Alcohol Prep via Reduction
The reactivity of hydride delivery agents can be fine-tuned by using derivatives with varying R-groups
Alkoxides
Cyano
Sterically hindered groups
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42. 13.4 Alcohol Prep via Reduction
LAH is strong enough to also reduce esters and carboxylic acids, whereas NaBH4 is generally not
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43. 13.4 Alcohol Prep via Reduction
To reduce an ester, 2 hydride equivalents are needed
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44. 13.4 Alcohol Prep via Reduction
To reduce an ester, 2 hydride equivalents are needed
Which steps in the mechanism are reversible?
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45. 13.4 Alcohol Prep via Reduction
Predict the products for the following processes
Practice with SkillBuilder 13.4
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46. 13.5 Preparation of Diols
Diols are named using the same method as alcohols, except the suffix, “diol” is used
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47. 13.5 Preparation of Diols
If two carbonyl groups are present, and enough moles of reducing agent are added, both can be reduced
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48. 13.5 Preparation of Diols
Recall the methods we discussed in chapter 9 to convert an alkene into a diol
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49. 13.6 Grignard Reactions
Grignard reagents are often used in the synthesis of alcohols
To form a Grignard, an alkyl halide is treated with Mg metal
How does the oxidation state of the carbon change upon forming the Grignard?
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50. 13.6 Grignard Reactions
The electronegativity difference between C (2.5) and Mg (1.3) is great enough that the bond has significant ionic character
The carbon atom is not able to effectively stabilize the negative charge it carries
Will it act as an acid, base, electrophile, nucleophile, etc.?
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51. 13.6 Grignard Reactions
If the Grignard reagent reacts with a carbonyl compound, an alcohol can result
Note the similarities between the Grignard and LAH mechanisms
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52. 13.6 Grignard Reactions
Because the Grignard is both a strong base and a strong nucleophile, care must be taken to protect it from exposure to water
If water can’t be used as the solvent, what solvent is appropriate?
What techniques are used to keep atmospheric moisture out of the reaction?
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Klein, Organic Chemistry 2e

53. 13.6 Grignard Reactions Grignard examples
With an ester substrate, excess Grignard reagent is required. WHY? Propose a mechanism
List some functional groups that are NOT compatible with the Grignard
Practice with SkillBuilder 13.5
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Klein, Organic Chemistry 2e

54. 13.6 Grignard Reactions
Design a synthesis for the following molecules starting from an alkyl halide and a carbonyl, each having 5 carbons or less
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55. 13.7 Protection of Alcohols
Consider the reaction below. WHY won’t it work?
The alcohol can act as an acid, especially in the presence of reactive reagents like the Grignard reagent
The alcohol can be protected to prevent it from reacting
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56. 13.7 Protection of Alcohols
A three-step process is required to achieve the desired overall synthesis
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57. 13.7 Protection of Alcohols
One such protecting group is trimethylsilyl (TMS)
The TMS protection step requires the presence of a base. Propose a mechanism
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58. 13.7 Protection of Alcohols
Evidence suggests that substitution at the Si atom occurs by an SN2 mechanism
Because Si is much larger than C, it is more open to backside attack
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59. 13.7 Protection of Alcohols
The TMS group can later be removed with H3O+ or F-
TBAF is often used to supply fluoride ions
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60. 13.7 Protection of Alcohols
Practice with conceptual checkpoint 13.18
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61. 13.8 Preparation of Phenols
2 million tons of phenol is produced industrially yearly
Acetone is a useful byproduct
Phenol is a precursor in many chemical syntheses
Pharmaceuticals
Polymers
Adhesives
Food preservatives, etc.
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62. 13.9 Reactions of Alcohols Recall this SN1 reaction from section 7.5
For primary alcohols, the reaction occurs by an SN2
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63. 13.9 Reactions of Alcohols
The SN2 reaction also occurs with ZnCl2 as the reagent
Recall from section 7.8 that the –OH group can be converted into a better leaving groups such as a tosyl group
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64. 13.9 Reactions of Alcohols
SOCl2 can also be used to convert an alcohol to an alkyl chloride
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65. 13.9 Reactions of Alcohols
PBr3 can also be used to convert an alcohol to an alkyl bromide
Note that the last step of the SOCl2 and PBr3 mechanisms are SN2
Practice with SkillBuilder 13.6
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Klein, Organic Chemistry 2e

66. 13.9 Reactions of Alcohols
Fill in the necessary reagents for the conversions below
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67. 13.9 E1 and E2 Reactions of Alcohols
In section 8.9, we saw that an acid (with a non-nucleophilic conjugate base) can promote E1
Why is E2 unlikely?
Recall that the reaction generally produces the more substituted alkene product
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68. 13.9 E1 and E2 Reactions of Alcohols
If the alcohol is converted into a better leaving group, then a strong base can be used to promote E2
E2 reactions do not involve rearrangements. WHY?
When applicable, E2 reactions also produce the more substituted product
Practice with conceptual checkpoint 13.21
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Klein, Organic Chemistry 2e

69. 13.10 Oxidation of Alcohols
We saw how alcohols can be formed by the reduction of a carbonyl
The reverse process is also possible with the right reagents
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70. 13.10 Oxidation of Alcohols
Oxidation of primary alcohols proceed to an aldehyde and subsequently to the carboxylic acid
Very few oxidizing reagents will stop at the aldehyde
Oxidation of secondary alcohols produces a ketone
Very few agents are capable of oxidizing the ketone
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71. 13.10 Oxidation of Alcohols
Tertiary alcohols generally do not undergo oxidation. WHY?
There are two main methods to produce the most common oxidizing agent, chromic acid
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72. 13.10 Oxidation of Alcohols
When chromic acid reacts with an alcohol, there are two main steps
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73. 13.10 Oxidation of Alcohols
Chromic acid will generally oxidize a primary alcohol to a carboxylic acid
PCC (pyridinium chlorochromate) can be used to stop at the aldehyde
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74. 13.10 Oxidation of Alcohols
PCC (pyridinium chlorochromate) is generally used with methylene chloride as the solvent
Both oxidizing agents will work with secondary alcohols
Practice with SkillBuilder 13.7
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Klein, Organic Chemistry 2e

75. 13.10 Oxidation of Alcohols
Predict the product for the following reaction
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76. 13.11 Biological Redox Reactions
Nature employs reducing and oxidizing agents
They are generally complex and selective. WHY?
NADH is one such reducing agent
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77. 13.11 Biological Redox Reactions
The reactive site of NADH acts as a hydride delivery agent
This is one way nature
converts carbonyls into
alcohols
Why is an enzyme required?
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78. 13.11 Biological Redox Reactions
NAD+ can undergo the reverse process
The NADH / NAD+
interconversion plays a
big role in metabolism
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79. 13.12 Oxidation of Phenol
Recall that tertiary alcohols do not undergo oxidation, because they lack an alpha proton
You might expect phenol to be similarly unreactive
Yet, phenol is even more readily oxidized than primary or secondary alcohols
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80. 13.12 Oxidation of Phenol
Phenol oxidizes to form benzoquinone, which in turn can be reduced to hydroquinone
Quinones are found everywhere in nature
They are ubiquitous
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81. 13.12 Oxidation of Phenol
Ubiquinones act to catalyze the conversion of oxygen into water, a key step in cellular respiration
Where in a cell do you think unbiquinones are most likely found?
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82. 13.12 Oxidation of Phenol Ubiquinone catalysis:
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83. 13.13 Synthetic Strategies
Recall some functional group conversions we learned
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84. 13.13 Synthetic Strategies
Classify the functional groups based on oxidation state
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85. 13.13 Synthetic Strategies Klein, Organic Chemistry 2e
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86. 13.13 Synthetic Strategies
Give necessary reagents for the following conversions
Practice with SkillBuilder 13.8
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87. 13.13 Synthetic Strategies
Recall the C-C bond forming reactions we learned
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88. 13.13 Synthetic Strategies
What if you want to convert an aldehyde into a ketone?
What reagents are needed for the following conversion?
Practice with conceptual checkpoint and SkillBuilder 13.9
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89. Additional Practice Problems
Name the following molecule
Draw (1R,2R)-1-(3,3-dimethylbutyl)-3,5-cyclohexadien-1,2-diol
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90. Additional Practice Problems
Use ARIO and solvation to rank the following molecules in order of increasing pKa
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91. Additional Practice Problems
Predict the products for the following processes
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92. Additional Practice Problems
Design a synthesis for the following molecule starting from an alkyl halide and a carbonyl, each having 5 carbons or less
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93. Additional Practice Problems
Give necessary reagents for the multi-step synthesis below
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