19.78 Write the products of the following sequences of reactions. Refer to your reaction road- maps to see how the combined reactions allow you to "navigate" between the different functional groups. Note that you will need your old Chapters 6-11 and Chapters 15-18 roadmaps along with your new Chapter 19 roadmap for these. (a) 1. BHS 2. H₂O₂ 3. H₂CrO4 4. SOCI₂ (b) 1. Cl₂/hv 2. KOLBU 3. H₂O, catalytic H₂SO4 4. H₂CrO4 Reaction Roadmap An alkene 5. EtOH 6.0.5 Equiv. NaOEt/EtOH 7. Mild H₂O An alkane 1.0 2. (CH3)₂S 3. H₂CrO (d) (c) 4. Excess EtOH, catalytic H₂SO OH 4. Mild H₂O* 5.0.5 Equiv. NaOEt/EtOH An alkene 6. Mild H₂O* A carboxylic acid 7. Mild H₂O* 1. SOC₁₂ 2. EtOH 3.0.5 Equiv. NaOEt/E:OH 5.1.0 Equiv. NaOEt 6. NH₂ (e) 1. 0.5 Equiv. NaOEt/EtOH 2. Mild H₂O* Br (f) i H An aldehyde 1. Catalytic NaOE/EtOH 2. H₂O*, heat 3. (CH,CH₂)₂Culi 4. Mild H₂O* 5.1.0 Equiv. LDA Br An ester 4. NaOH, H₂O 5. Mild H₂O* 6. Heat 7. MgBr 8. Mild H₂O* 7. Mild H₂O+

Organic Chemistry
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Chapter10: Alcohols
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19.78 Write the products of the following sequences of reactions. Refer to your reaction road-
maps to see how the combined reactions allow you to "navigate" between the different
functional groups. Note that you will need your old Chapters 6-11 and Chapters 15-18
roadmaps along with your new Chapter 19 roadmap for these.
(a)
1. BHS
2. H₂O₂
3. H₂CrO4
4. SOCI₂
(b)
1. Cl₂/hv
2. KOLBU
3. H₂O, catalytic H₂SO4
4. H₂CrO4
Reaction
Roadmap
An alkene 5. EtOH
6.0.5 Equiv. NaOEt/EtOH
7. Mild H₂O
An alkane
1.0
2. (CH3)₂S
3. H₂CrO
(d)
(c)
4. Excess EtOH, catalytic H₂SO
OH
4. Mild H₂O*
5.0.5 Equiv. NaOEt/EtOH
An alkene 6. Mild H₂O*
A carboxylic
acid
7. Mild H₂O*
1. SOC₁₂
2. EtOH
3.0.5 Equiv. NaOEt/E:OH
5.1.0 Equiv. NaOEt
6.
NH₂
(e)
1. 0.5 Equiv. NaOEt/EtOH
2. Mild H₂O*
Br
(f)
i
H
An aldehyde
1. Catalytic NaOE/EtOH
2. H₂O*, heat
3. (CH,CH₂)₂Culi
4. Mild H₂O*
5.1.0 Equiv. LDA
Br
An ester
4. NaOH, H₂O
5. Mild H₂O*
6. Heat
7.
MgBr
8. Mild H₂O*
7. Mild H₂O+
Transcribed Image Text:19.78 Write the products of the following sequences of reactions. Refer to your reaction road- maps to see how the combined reactions allow you to "navigate" between the different functional groups. Note that you will need your old Chapters 6-11 and Chapters 15-18 roadmaps along with your new Chapter 19 roadmap for these. (a) 1. BHS 2. H₂O₂ 3. H₂CrO4 4. SOCI₂ (b) 1. Cl₂/hv 2. KOLBU 3. H₂O, catalytic H₂SO4 4. H₂CrO4 Reaction Roadmap An alkene 5. EtOH 6.0.5 Equiv. NaOEt/EtOH 7. Mild H₂O An alkane 1.0 2. (CH3)₂S 3. H₂CrO (d) (c) 4. Excess EtOH, catalytic H₂SO OH 4. Mild H₂O* 5.0.5 Equiv. NaOEt/EtOH An alkene 6. Mild H₂O* A carboxylic acid 7. Mild H₂O* 1. SOC₁₂ 2. EtOH 3.0.5 Equiv. NaOEt/E:OH 5.1.0 Equiv. NaOEt 6. NH₂ (e) 1. 0.5 Equiv. NaOEt/EtOH 2. Mild H₂O* Br (f) i H An aldehyde 1. Catalytic NaOE/EtOH 2. H₂O*, heat 3. (CH,CH₂)₂Culi 4. Mild H₂O* 5.1.0 Equiv. LDA Br An ester 4. NaOH, H₂O 5. Mild H₂O* 6. Heat 7. MgBr 8. Mild H₂O* 7. Mild H₂O+
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