1. Saturated and Unsaturated Hydrocarbons
Saturated hydrocarbons have no double bonds.
Unsaturated hydrocarbons have one or more double bonds.
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2. Nomenclature of Alkenes
Replace “ane” of alkane with “ene.”
The functional group gets the lowest possible number.
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3. Stereoisomers are Named Using a cis or trans Prefix
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4. Nomenclature of Dienes
two double bonds = diene
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5. Nomenclature of Alkenes
Number in the direction so that the functional group gets the lowest number.
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6. Nomenclature of Alkenes
Substituents are stated in alphabetical order.
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7. Nomenclature of Alkenes
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8. Nomenclature of Cyclic Alkenes
A number is not needed to denote the position of the functional group;
it is always between C1 and C2.
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9. Nomenclature of Alkenes
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10. Nomenclature of Alkenes
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11. Vinylic and Allylic Carbons
vinylic carbon: the sp2 carbon of an alkene
allylic carbon: a carbon adjacent to a vinylic carbon
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12. Double Bonds Have Restricted Rotation
Rotation about a double bond breaks the π bond.
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13. Double Bonds Have Restricted Rotation
Double bonds restrict rotation.
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14. Six Atoms of an Alkene are in the Same Plane
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15. Alkenes Have Cis–Trans Isomers
Cis: The hydrogens are on the same side of the ring.
Trans: The hydrogens are on opposite sides of the ring.
They have different configurations; they can be separated.
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16. Some Alkenes Do Not Have Cis–Trans Isomers
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17. Cis–Trans Isomers
Cis–trans isomers have different physical properties.
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18. Which Is Cis and Which Is Trans?
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19. The E,Z System of Nomenclature
Z = Zusammen (together)
E = Entgegen (opposite)
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20. Relative Priorities
The relative priorities of the two groups depends on the atomic numbers of the atoms attached to the sp2 carbon.
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21. The E and Z Isomers
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22. E and Z
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23. E and Z
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24. Isomers for Compounds with
Two Double Bonds
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25. Addition of Hydrogen Halides
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26. Which sp2 Carbon Gets the H+?
סיפוח HCl לפי כלל מרקובניקוב
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27. The Mechanism Carbocation formation is the rate-limiting step.
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28. Relative Stabilities of Carbocations
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29. Carbocation Stability
Alkyl groups decrease the concentration of positive charge on the carbon.
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30. Hyperconjugation Stabilizes a Carbocation
רשות
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31. Stabilization by Hyperconjugation
רשות
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32. Hyperconjugation
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33. It Looks Like What it is Closer To
The Hammond postulate says that the transition state is more similar in structure to the species to which it is more similar in energy.
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34. Why the Difference in Rate?
The more stable carbocation is formed more rapidly.
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35. The Difference in Carbocation Stability Determines the Products
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36. What Product Will Be Formed?
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37. The Electrophile Adds to the sp2 Carbon Bonded to the Most Hydrogens
A regioselective reaction forms more of one constitutional isomer than another.
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38. Not Regioselective
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39. Acid-Catalyzed Addition of Water
סיפוח מים בקטליזה חומצית לפי כלל מרקובניקוב
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40. Mechanism for the Acid-Catalyzed Addition of Water
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41. Acid-Catalyzed Addition of an Alcohol
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42. Acid-Catalyzed Addition of an Alcohol
Mechanism for the
Acid-Catalyzed Addition of an Alcohol
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43. The Major Product is a Surprise
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44. The Major Product is a Surprise
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45. Carbocation Rearrangement
(a 1,2-hydride shift)
שחלוף מרחיב טבעת
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46. Carbocation Rearrangement
(a 1,2-methyl shift)
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47. The Carbocation Does Not Rearrange
(No Improvement in Carbocation Stability)
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48. Addition of HBr in the Presence of Peroxide
ניתן לרשום על החץ Radical
peroxide (ROOR)
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49. Mechanism for the Addition of HBr in the Presence of Peroxide
רשות
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50. A Carbocation Intermediate is Not Formed,
So a Carbocation Rearrangement Does Not Occur
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51. Peroxide Effect Occurs Only with HBr
עם HCl ו- HI הסיפוח רק מרקובניקוב. עם HBr הסיפוח גם מרקובניקוב וגם אנטי מרקובניקוב ( רדיקלי)
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52. BH3 is an Electrophile
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53. Hydroboration–Oxidation
סיפוח מים אנטי מרקובניקוב
THF
ממס
ניתן לרשום גם B2H6 במקוםBH3
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54. The Electrophile Adds to the sp2 Carbon Bonded to the Most Hydrogens
The reagents are numbered because the second set of reagents is not added until the first reaction is over.
סיפוח מים מרקובניקוב
סיפוח מים אנטי מרקובניקוב
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55. Mechanism for Hydroboration
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56. Addition of BH3 and Addition of HBr Follow the Same Rule
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57. BH3 Has Three Potential Hydride Ions So
a Dialkylborane and a Trialkylborane Can Be Formed
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58. The Mechanism is the Same
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59. OH Replaces BR2
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60. Mechanism for the Oxidation Reaction
רשות
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61. No Carbocation Rearrangements
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62. Addition of Br2 or Cl2
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63. The Product is a Vicinal Dihalide
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64. The Mechanism for the Addition of a Halogen
The intermediate is a cyclic bromonium ion.
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65. A Cyclic Bromonium Ion The carbons are the most electrophilic atoms.
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66. No Carbocation Rearrangements
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67. Alkenes Do Not Add I2
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68. Formation of Halohydrins
הברום נקשר לפחמן המכיל יותר מימנים
ניתן לרשום HOX במקום X2 + H2O
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69. Mechanism for Halohydrin Formation
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70. Why Does it Follow the Same Rule?
The electrophile adds to the sp2 carbon
bonded to the most hydrogens.
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71. More Reactions
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72. Formation of an Epoxide
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73. An Oxygen–Oxygen Single Bond
is a Weak Bond
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74. MCPBA is a Commonly Used Peroxyacid
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75. Mechanism for Epoxidation
רשות
the mechanism is similar to that for the addition of Br2
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76. Ozonolysis
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77. Mechanism for Ozonide Formation
רשות
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78. The Ozonide is Converted to Ketones and/or Aldehydes
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79. Ketones and Aldehydes
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80. Ozonolysis
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81. Ozonolysis
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82. What Alkene Gave the Ozonolysis Products?
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83. אוזונוליזה
אם הפחמן של הקשר הכפול, קשור למימן, אזי מתקבל אלדהיד בתנאי חיזור, וחומצה קרבוקסילית בתנאי חימצון
NaBH4 מחזר קרבוניל לכוהל
שאלה
פתרון
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84. תגובה עם KMnO4 potassium permanganate: KMnO4
1,2-diols are also known as vicinal diols or vicinal glycols
תנאים עדינים
מנגנון: רשות
סיפוח סין
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85. תגובה עם KMnO4 -תנאים חריפים
בתנאים חומציים או עם בסיס חם מתרחש ביקוע מחמצן
אם פחמן הקשר הכפול, קשור למימן אחד מתקבלת חומצה קרבוקסילית
אם פחמן הקשר הכפול, קשור לשני מימנים ( טרמינלי) מתקבל CO2
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86. Addition of Hydrogen catalytic hydrogenation a reduction reaction
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87. Mechanism for Hydrogen Addition
רשות
catalytic hydrogenation
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88. Relative Stabilities of Alkenes
The more substituents there are the greater the stabilization of the alkene
Stability order due to two factors
Hyperconjugation
Stabilizing interaction between the C=C  bond and adjacent C-H σ bonds on substituents
Bond strength
A bond between an sp2 carbon and an sp3 carbon is somewhat stronger than a bond between two sp3 carbons
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89. The Cis Isomer Has Steric Strain
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90. The Relative Stabilities of Disubstituted Alkenes
relative stabilities of dialkyl-substituted alkenes
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91. The Product Does Not Have Stereoisomers
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92. The Product is a Racemic Mixture
When a reactant that does not have an asymmetric center
forms a product that has one asymmetric center,
the product is a racemic mixture.
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93. Formation of a Racemic Mixture
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94. Formation of a Second Asymmetric Center
When a reactant that has an asymmetric center forms a product that has new asymmetric center, the product is a pair of diastereomers.
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95. Only Syn Addition
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96. Syn Addition to a Cis Isomer Forms Only the Erythro Stereoisomers
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97. If the Substituents are the Same,
the Erythro Stereoisomer is a Meso Compound
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98. Syn Addition to a Trans Isomer Forms Only the Threo Stereoisomers
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99. תרגיל-סיפוח מימן לקשר כפול- סין
שאלה
A מתקבל יותר, דיאסטריומרים
תשובה
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100. Syn Addition to a Cis Isomer Forms Only the Cis Stereoisomers
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101. Syn Addition to a Trans Isomer Forms Only the Trans Stereoisomers
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102. If the Substituents are the Same,
the Cis Stereoisomer is a Meso Compound
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103. Only Syn Addition
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104. to the Same Side of the Ring
The H and OH Add
to the Same Side of the Ring
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105. Addition of a Halogen is an Anti Addition
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106. Anti Addition to a Cis Isomer Forms Only the Threo Stereoisomers
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107. If the Substituents are the Same,
the Cis Stereoisomer is a Meso Compound
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108. If the Substituents are the Same,
the Erythro Stereoisomer is a Meso Compound
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109. Anti Addition to a Cis Isomer Forms Only the Trans Stereoisomers
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111. An Enzyme Forms One Stereoisomer; It is Completely Stereoselective
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112. An Enzyme Can Block One Side of the Reactant
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113. An Enzyme Reacts with Only One Stereoisomer;
It is Completely Stereospecific
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114. Compounds That Can Be Formed from an Alkene
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115. antioxidants( העשרה)
Two examples of radical inhibitors that are present in biological systems are vitamin
C and vitamin E. Like hydroquinone, they form relatively stable radicals. Vitamin
C (also called ascorbic acid) is a water-soluble compound that traps radicals formed in the aqueous environment of the cell and in blood plasma. Vitamin E (also called  -tocopherol) is a water-insoluble (hence fat-soluble) compound that traps radicals
formed in nonpolar membranes. Why one vitamin functions in aqueous environments
and the other in nonaqueous environments should be apparent from their structures
, which show that vitamin C is a relatively polar compound, whereas vitamin E is nonpolar
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