![Page 1: CH.5 + 6 - ALKENES AND REACTIONS OF ALKENESlightcat-files.s3.amazonaws.com/...brown...ch-5-6-alkenes-and-reactions-of-alkenes-703.pdfSame as the general mechanism hydrohalogenation,](https://reader033.vdocuments.mx/reader033/viewer/2022041914/5e68d7baf8dfd81e8f5fa752/html5/thumbnails/1.jpg)
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ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
![Page 2: CH.5 + 6 - ALKENES AND REACTIONS OF ALKENESlightcat-files.s3.amazonaws.com/...brown...ch-5-6-alkenes-and-reactions-of-alkenes-703.pdfSame as the general mechanism hydrohalogenation,](https://reader033.vdocuments.mx/reader033/viewer/2022041914/5e68d7baf8dfd81e8f5fa752/html5/thumbnails/2.jpg)
CONCEPT: ALKENES and ALKYNES
□ Alkenes/Alkynes are named by adding the suffix modifier (-________/-________) to the end of the root.
● Alkenes/alkynes receive ___________________ in numbering alkanes
● Location is assigned to the first double bonded carbon
EXAMPLE: Name the following compound:
a.
ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
Page 2
![Page 3: CH.5 + 6 - ALKENES AND REACTIONS OF ALKENESlightcat-files.s3.amazonaws.com/...brown...ch-5-6-alkenes-and-reactions-of-alkenes-703.pdfSame as the general mechanism hydrohalogenation,](https://reader033.vdocuments.mx/reader033/viewer/2022041914/5e68d7baf8dfd81e8f5fa752/html5/thumbnails/3.jpg)
CONCEPT: STABILITY OF ALKENES
□ Alkenes are also stabilized through _________________________________
● Since this is only possible with -R groups, the more substituted the alkene, the more ________________
EXAMPLE: Rank the following alkenes in order of lowest to highest heat of combustion.
ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
Page 3
![Page 4: CH.5 + 6 - ALKENES AND REACTIONS OF ALKENESlightcat-files.s3.amazonaws.com/...brown...ch-5-6-alkenes-and-reactions-of-alkenes-703.pdfSame as the general mechanism hydrohalogenation,](https://reader033.vdocuments.mx/reader033/viewer/2022041914/5e68d7baf8dfd81e8f5fa752/html5/thumbnails/4.jpg)
CONCEPT: CARBOCATION INTERMEDIATES — STABILITY
□ Carbocations are stabilized by a phenomenon called _________________________________
● Hyperconjugation is the delocalization of charge by the interaction of an empty p-orbital with an adjacent, eclipsed σ-bond
● Since this is only possible with -R groups, the more substituted the carbocation, the more ________________
EXAMPLE: Which of the following alkyl halides would generate the most stable carbocation?
ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
Page 4
![Page 5: CH.5 + 6 - ALKENES AND REACTIONS OF ALKENESlightcat-files.s3.amazonaws.com/...brown...ch-5-6-alkenes-and-reactions-of-alkenes-703.pdfSame as the general mechanism hydrohalogenation,](https://reader033.vdocuments.mx/reader033/viewer/2022041914/5e68d7baf8dfd81e8f5fa752/html5/thumbnails/5.jpg)
CONCEPT: CARBOCATION INTERMEDIATES — REARRANGEMENTS
□ Carbocations will rearrange to an adjacent, more stable position if possible. This is called a ___________
● 1,2-Hydride Shift occurs when there is a ____________ located on an adjacent, more stable carbon.
● 1,2-Alkyl Shift occurs when only small __________ groups are located on an adjacent, more stable carbon.
● Ring Expansion occurs when a carbocation is adjacent to a 3, 4 or 5- membered ring.
ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
Page 5
![Page 6: CH.5 + 6 - ALKENES AND REACTIONS OF ALKENESlightcat-files.s3.amazonaws.com/...brown...ch-5-6-alkenes-and-reactions-of-alkenes-703.pdfSame as the general mechanism hydrohalogenation,](https://reader033.vdocuments.mx/reader033/viewer/2022041914/5e68d7baf8dfd81e8f5fa752/html5/thumbnails/6.jpg)
PRACTICE: Which of the following carbocations would be likely to rearrange? Draw each rearranged structure below.
ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
Page 6
![Page 7: CH.5 + 6 - ALKENES AND REACTIONS OF ALKENESlightcat-files.s3.amazonaws.com/...brown...ch-5-6-alkenes-and-reactions-of-alkenes-703.pdfSame as the general mechanism hydrohalogenation,](https://reader033.vdocuments.mx/reader033/viewer/2022041914/5e68d7baf8dfd81e8f5fa752/html5/thumbnails/7.jpg)
CONCEPT: GENERAL MECHANISM
□ Addition reactions are ones in which 1 ______ bond is broken and 2 new ______ bonds are formed.
● They are the inverse of ___________________ reactions
EXAMPLE: Provide the mechanism for the following addition reaction.
ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
Page 7
![Page 8: CH.5 + 6 - ALKENES AND REACTIONS OF ALKENESlightcat-files.s3.amazonaws.com/...brown...ch-5-6-alkenes-and-reactions-of-alkenes-703.pdfSame as the general mechanism hydrohalogenation,](https://reader033.vdocuments.mx/reader033/viewer/2022041914/5e68d7baf8dfd81e8f5fa752/html5/thumbnails/8.jpg)
CONCEPT: MARKOVNIKOV’S RULE
□ When we try to perform addition on asymmetric double bonds, we now get two possible products.
● Markovnikov’s Rule predicts that the carbocation will ALWAYS form on the _________ _______________ carbon
EXAMPLE: Provide the mechanism for the following addition reaction.
ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
Page 8
![Page 9: CH.5 + 6 - ALKENES AND REACTIONS OF ALKENESlightcat-files.s3.amazonaws.com/...brown...ch-5-6-alkenes-and-reactions-of-alkenes-703.pdfSame as the general mechanism hydrohalogenation,](https://reader033.vdocuments.mx/reader033/viewer/2022041914/5e68d7baf8dfd81e8f5fa752/html5/thumbnails/9.jpg)
CONCEPT: HYDROHALOGENATION
General Reaction:
EXAMPLE: Provide the mechanism for the following addition reaction.
ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
Page 9
![Page 10: CH.5 + 6 - ALKENES AND REACTIONS OF ALKENESlightcat-files.s3.amazonaws.com/...brown...ch-5-6-alkenes-and-reactions-of-alkenes-703.pdfSame as the general mechanism hydrohalogenation,](https://reader033.vdocuments.mx/reader033/viewer/2022041914/5e68d7baf8dfd81e8f5fa752/html5/thumbnails/10.jpg)
CONCEPT: ACID-CATALYZED HYDRATION
● Same reagents as acid-catalyzed dehydration, except starting with a _____________ __________ instead of an alcohol.
● Same as the general mechanism hydrohalogenation, except with _____________ as the nucleophile
● Remember that EVERY acid-cat. mechanism begins with ________________ and ends with ________________
General Reaction:
EXAMPLE: Provide the mechanism for the following addition reaction.
ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
Page 10
![Page 11: CH.5 + 6 - ALKENES AND REACTIONS OF ALKENESlightcat-files.s3.amazonaws.com/...brown...ch-5-6-alkenes-and-reactions-of-alkenes-703.pdfSame as the general mechanism hydrohalogenation,](https://reader033.vdocuments.mx/reader033/viewer/2022041914/5e68d7baf8dfd81e8f5fa752/html5/thumbnails/11.jpg)
PRACTICE: Provide the mechanism and predict the product of the following reaction.
ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
Page 11
![Page 12: CH.5 + 6 - ALKENES AND REACTIONS OF ALKENESlightcat-files.s3.amazonaws.com/...brown...ch-5-6-alkenes-and-reactions-of-alkenes-703.pdfSame as the general mechanism hydrohalogenation,](https://reader033.vdocuments.mx/reader033/viewer/2022041914/5e68d7baf8dfd81e8f5fa752/html5/thumbnails/12.jpg)
CONCEPT: OXYMERCURATION-REDUCTION
General Reaction:
Mechanism:
1. Electrophilic Addition
2. Nucleophilic Substitution (SN2)
3. Reduction (demurcuration)
ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
Page 12
![Page 13: CH.5 + 6 - ALKENES AND REACTIONS OF ALKENESlightcat-files.s3.amazonaws.com/...brown...ch-5-6-alkenes-and-reactions-of-alkenes-703.pdfSame as the general mechanism hydrohalogenation,](https://reader033.vdocuments.mx/reader033/viewer/2022041914/5e68d7baf8dfd81e8f5fa752/html5/thumbnails/13.jpg)
PRACTICE: Provide the mechanism and predict the product of the following reactions.
a.
ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
Page 13
![Page 14: CH.5 + 6 - ALKENES AND REACTIONS OF ALKENESlightcat-files.s3.amazonaws.com/...brown...ch-5-6-alkenes-and-reactions-of-alkenes-703.pdfSame as the general mechanism hydrohalogenation,](https://reader033.vdocuments.mx/reader033/viewer/2022041914/5e68d7baf8dfd81e8f5fa752/html5/thumbnails/14.jpg)
CONCEPT: HYDROBORATION-OXIDATION
General Reaction:
Mechanism:
1. Electrophilic Addition
2. Oxidation
ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
Page 14
![Page 15: CH.5 + 6 - ALKENES AND REACTIONS OF ALKENESlightcat-files.s3.amazonaws.com/...brown...ch-5-6-alkenes-and-reactions-of-alkenes-703.pdfSame as the general mechanism hydrohalogenation,](https://reader033.vdocuments.mx/reader033/viewer/2022041914/5e68d7baf8dfd81e8f5fa752/html5/thumbnails/15.jpg)
PRACTICE: Provide the mechanism and predict the product of the following reactions.
a.
b.
ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
Page 15
![Page 16: CH.5 + 6 - ALKENES AND REACTIONS OF ALKENESlightcat-files.s3.amazonaws.com/...brown...ch-5-6-alkenes-and-reactions-of-alkenes-703.pdfSame as the general mechanism hydrohalogenation,](https://reader033.vdocuments.mx/reader033/viewer/2022041914/5e68d7baf8dfd81e8f5fa752/html5/thumbnails/16.jpg)
CONCEPT: CATALYTIC HYDROGENATION AND WILKINSON’S CATALYST
General Reaction:
PRACTICE: Provide the products for the following reaction.
ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
Page 16
![Page 17: CH.5 + 6 - ALKENES AND REACTIONS OF ALKENESlightcat-files.s3.amazonaws.com/...brown...ch-5-6-alkenes-and-reactions-of-alkenes-703.pdfSame as the general mechanism hydrohalogenation,](https://reader033.vdocuments.mx/reader033/viewer/2022041914/5e68d7baf8dfd81e8f5fa752/html5/thumbnails/17.jpg)
CONCEPT: INTRO TO REDOX
● Oxidation reactions involve an increase in the ______________ content of a molecule
● Reduction reactions involve an increase in the ______________ content of a molecule
EXAMPLE: Label the following transformations as oxidation or reduction.
a.
b.
c.
ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
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CONCEPT: HALOGENATION
General Reaction:
Mechanism:
1. Electrophilic Addition
2. Nucleophilic Substitution (SN2)
ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
Page 18
![Page 19: CH.5 + 6 - ALKENES AND REACTIONS OF ALKENESlightcat-files.s3.amazonaws.com/...brown...ch-5-6-alkenes-and-reactions-of-alkenes-703.pdfSame as the general mechanism hydrohalogenation,](https://reader033.vdocuments.mx/reader033/viewer/2022041914/5e68d7baf8dfd81e8f5fa752/html5/thumbnails/19.jpg)
CONCEPT: HALOHYDRIN FORMATION
General Reaction:
Mechanism:
1. Electrophilic Addition
2. Nucleophilic Substitution (SN2)
ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
Page 19
![Page 20: CH.5 + 6 - ALKENES AND REACTIONS OF ALKENESlightcat-files.s3.amazonaws.com/...brown...ch-5-6-alkenes-and-reactions-of-alkenes-703.pdfSame as the general mechanism hydrohalogenation,](https://reader033.vdocuments.mx/reader033/viewer/2022041914/5e68d7baf8dfd81e8f5fa752/html5/thumbnails/20.jpg)
PRACTICE: Provide the mechanism and predict the product of the following reactions.
a.
b.
ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
Page 20
![Page 21: CH.5 + 6 - ALKENES AND REACTIONS OF ALKENESlightcat-files.s3.amazonaws.com/...brown...ch-5-6-alkenes-and-reactions-of-alkenes-703.pdfSame as the general mechanism hydrohalogenation,](https://reader033.vdocuments.mx/reader033/viewer/2022041914/5e68d7baf8dfd81e8f5fa752/html5/thumbnails/21.jpg)
CONCEPT: SYN VICINAL DIHYDROXYLATION
General Reaction:
EXAMPLE: Predict the product for the following multi-step reaction.
ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
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![Page 22: CH.5 + 6 - ALKENES AND REACTIONS OF ALKENESlightcat-files.s3.amazonaws.com/...brown...ch-5-6-alkenes-and-reactions-of-alkenes-703.pdfSame as the general mechanism hydrohalogenation,](https://reader033.vdocuments.mx/reader033/viewer/2022041914/5e68d7baf8dfd81e8f5fa752/html5/thumbnails/22.jpg)
CONCEPT: WEAK OXIDATIVE CLEAVAGE
Ozonolysis: Ketones + Aldehydes + Formaldehyde
PRACTICE: Predict the products of the following reaction
ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
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![Page 23: CH.5 + 6 - ALKENES AND REACTIONS OF ALKENESlightcat-files.s3.amazonaws.com/...brown...ch-5-6-alkenes-and-reactions-of-alkenes-703.pdfSame as the general mechanism hydrohalogenation,](https://reader033.vdocuments.mx/reader033/viewer/2022041914/5e68d7baf8dfd81e8f5fa752/html5/thumbnails/23.jpg)
CONCEPT: OZONOLYSIS – FULL MECHANISM
The mechanism for ozonolysis proceeds through multiple intermediates.
●Ozonolysis is combined with either a reductive, or an oxidative workup
□ Reductive workup: S(CH3)2 or Zn/HOAc
□ Oxidative Workup: H2O2
Ozonolysis Mechanism:
Reductive Workup Mechanism:
Oxidative Workup Mechanism:
ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
Page 23
![Page 24: CH.5 + 6 - ALKENES AND REACTIONS OF ALKENESlightcat-files.s3.amazonaws.com/...brown...ch-5-6-alkenes-and-reactions-of-alkenes-703.pdfSame as the general mechanism hydrohalogenation,](https://reader033.vdocuments.mx/reader033/viewer/2022041914/5e68d7baf8dfd81e8f5fa752/html5/thumbnails/24.jpg)
PRACTICE: Predict the products and show the full mechanism for the following reaction
ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
Page 24
![Page 25: CH.5 + 6 - ALKENES AND REACTIONS OF ALKENESlightcat-files.s3.amazonaws.com/...brown...ch-5-6-alkenes-and-reactions-of-alkenes-703.pdfSame as the general mechanism hydrohalogenation,](https://reader033.vdocuments.mx/reader033/viewer/2022041914/5e68d7baf8dfd81e8f5fa752/html5/thumbnails/25.jpg)
CONCEPT: OXIDATIVE CLEAVAGE
Strong Oxidative Cleavage: Ketones + Carboxylic Acid + Carbon Dioxide
PRACTICE: Predict the product of the following reaction.
ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
Page 25
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CONCEPT: OXIDATIVE CLEAVAGE
Cleavage of Alkynes: Carboxylic Acid + Carbon Dioxide
EXAMPLE: Predict the product of the following reaction.
ORGANIC - BROWN 7E
CH.5 + 6 - ALKENES AND REACTIONS OF ALKENES
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