Radical rearrangement reactions have wide applications in organic synthesis.

<MultiModal>![C#CCCC1(C(O[Si](C)(C)C)CC#C)CC(C)(C)C=C1O[Si](C)(C)C>[Bu_3SnH].[AIBN]>[A],A is the reaction product. After the reaction is complete, $HCl$ is added.](/media/uploads/24b06546-469a-4d38-9f4b-4ffc8e6cad04.png)</MultiModal>

<MultiModal>![C#CCCC1(CC(C)(C=C1O[Si](C)(C)C)C)C(C/C([X])=C/[Sn](CCCC)(CCCC)CCCC)O[Si](C)(C)C,X is a single electron, Option 1](/media/uploads/cbc02d9d-b0a7-42a6-9c7a-4b7156b3d641.png)</MultiModal>

Option 1

<MultiModal>![C#CCCC1(CC(C)(C=C1O[Si](C)(C)C)C)C(C/C([X])=C/[Sn](CCCC)(CCCC)CCCC)O[Si](C)(C)C,X is a single electron, Option 2](/media/uploads/a8f3dda4-c542-4972-983a-5cb15b6d3658.png)</MultiModal>

Option 2

<MultiModal>![C#CCC(C1(CC(C)(C(C1/2O[Si](C)(C)C)[X])C)CCC2=C\[Sn](CCCC)(CCCC)CCCC)O[Si](C)(C)C,X is a single electron, Option 3](/media/uploads/7771579e-10b4-4dca-83d6-dd78e25b8647.png)</MultiModal>

Option 3

<MultiModal>![CC1(C([X])C2(C(CCC#C)(C1)C(C/C2=C\[Sn](CCCC)(CCCC)CCCC)O[Si](C)(C)C)O[Si](C)(C)C)C,X is a single electron, Option 4](/media/uploads/59521824-d3c6-4213-8036-d94eecee681d.png)</MultiModal>

Option 4

<MultiModal>![CC1(C2C(C(CCC#C)(C1)C(C/C2=C\[Sn](CCCC)(CCCC)CCCC)O[Si](C)(C)C)([X])O[Si](C)(C)C)C,X is a single electron, Option 5](/media/uploads/ce469ae4-58cf-450f-9471-d04a5a675624.png)</MultiModal>

Option 5

<MultiModal>![CC1(C2C(C(C(CC#C)O[Si](C)(C)C)(C1)CC/C2=C\[Sn](CCCC)(CCCC)CCCC)([X])O[Si](C)(C)C)C,X is a single electron, Option 6](/media/uploads/b84b4844-c2f6-4d22-a759-6d5750e98c5f.png)</MultiModal>

Option 6

<MultiModal>![CC1(C2C3(C(C(C/C2=C([X])\[H])O[Si](C)(C)C)(C1)CC/C3=C\[Sn](CCCC)(CCCC)CCCC)O[Si](C)(C)C)C,X is a single electron, Option 7](/media/uploads/43bd4ba1-5688-4df8-8706-bd6af09d00d0.png)</MultiModal>

Option 7

<MultiModal>![CC1(C2C3(C(CC/C2=C([X])\[H])(C1)C(C/C3=C\[Sn](CCCC)(CCCC)CCCC)O[Si](C)(C)C)O[Si](C)(C)C)C,X is a single electron, Option 8](/media/uploads/6dc16aaa-d6f4-4d9f-b65d-9a0c741ca8b6.png)</MultiModal>

Option 8

Without considering enantiomers, please select all possible intermediates in the options.
自由基重排反应在有机合成中有着广泛的应用

<MultiModal>![C#CCCC1(C(O[Si](C)(C)C)CC#C)CC(C)(C)C=C1O[Si](C)(C)C>[Bu_3SnH].[AIBN]>[A],A是反应产物，反应完成后加入$HCl$](/media/uploads/24b06546-469a-4d38-9f4b-4ffc8e6cad04.png)</MultiModal>

<MultiModal>![C#CCCC1(CC(C)(C=C1O[Si](C)(C)C)C)C(C/C([X])=C/[Sn](CCCC)(CCCC)CCCC)O[Si](C)(C)C,X为单电子,选项1](/media/uploads/cbc02d9d-b0a7-42a6-9c7a-4b7156b3d641.png)</MultiModal>

选项1

<MultiModal>![C#CCCC1(CC(C)(C=C1O[Si](C)(C)C)C)C(C/C([X])=C/[Sn](CCCC)(CCCC)CCCC)O[Si](C)(C)C,X为单电子,选项2](/media/uploads/a8f3dda4-c542-4972-983a-5cb15b6d3658.png)</MultiModal>

选项2

<MultiModal>![C#CCC(C1(CC(C)(C(C1/2O[Si](C)(C)C)[X])C)CCC2=C\[Sn](CCCC)(CCCC)CCCC)O[Si](C)(C)C,X是单电子,选项3](/media/uploads/7771579e-10b4-4dca-83d6-dd78e25b8647.png)</MultiModal>

选项3

<MultiModal>![CC1(C([X])C2(C(CCC#C)(C1)C(C/C2=C\[Sn](CCCC)(CCCC)CCCC)O[Si](C)(C)C)O[Si](C)(C)C)C,X是单电子，选项4](/media/uploads/59521824-d3c6-4213-8036-d94eecee681d.png)</MultiModal>

选项4

<MultiModal>![CC1(C2C(C(CCC#C)(C1)C(C/C2=C\[Sn](CCCC)(CCCC)CCCC)O[Si](C)(C)C)([X])O[Si](C)(C)C)C,X是单电子,选项5](/media/uploads/ce469ae4-58cf-450f-9471-d04a5a675624.png)</MultiModal>

选项5

<MultiModal>![CC1(C2C(C(C(CC#C)O[Si](C)(C)C)(C1)CC/C2=C\[Sn](CCCC)(CCCC)CCCC)([X])O[Si](C)(C)C)C,X是单电子,选项6](/media/uploads/b84b4844-c2f6-4d22-a759-6d5750e98c5f.png)</MultiModal>

选项6

<MultiModal>![CC1(C2C3(C(C(C/C2=C([X])\[H])O[Si](C)(C)C)(C1)CC/C3=C\[Sn](CCCC)(CCCC)CCCC)O[Si](C)(C)C)C,X是单电子,选项7](/media/uploads/43bd4ba1-5688-4df8-8706-bd6af09d00d0.png)</MultiModal>

选项7

<MultiModal>![CC1(C2C3(C(CC/C2=C([X])\[H])(C1)C(C/C3=C\[Sn](CCCC)(CCCC)CCCC)O[Si](C)(C)C)O[Si](C)(C)C)C,X是单电子,选项8](/media/uploads/6dc16aaa-d6f4-4d9f-b65d-9a0c741ca8b6.png)</MultiModal>

选项8

不考虑对映异构的情况下，请选出选项中所有可能的中间体
All other options are incorrect
Option 1, 3, 5
Option 2, 4, 5
Option 1, 3, 7
Option 2, 4, 8
Options 1, 3, 6
Option 2, 5
Options 2, 5, 6
Options 1, 4, 6
其他选项均不正确
选项1、3、5
选项2、4、5
选项1、3、7
选项2、4、8
选项1、3、6
选项2、5
选项2、5、6
选项1、4、6
The carbon radical with the electron-withdrawing group $-OTMS$ introduced at the $\gamma$ position is relatively unstable.

<Checkpoint>[The carbon radical with the electron-withdrawing group $-OTMS$ introduced at the $\gamma$ position is relatively unstable](1)</Checkpoint>

First, an intermediate is formed.

<MultiModal>![C#CCCC1(CC(C)(C=C1O[Si](C)(C)C)C)C(C/C([X])=C/[Sn](CCCC)(CCCC)CCCC)O[Si](C)(C)C,X为单电子](/media/uploads/cbc02d9d-b0a7-42a6-9c7a-4b7156b3d641.png)</MultiModal>

<Checkpoint>[First, an intermediate is formed: C#CCCC1(CC(C)(C=C1O[Si](C)(C)C)C)C(C/C([X])=C/[Sn](CCCC)(CCCC)CCCC)O[Si](C)(C)C,X is single electron](1)</Checkpoint>

The reaction rate of 5-exo-trig is faster.

<Checkpoint>[The reaction rate of 5-exo-trig is faster](1)</Checkpoint>

Therefore, the intermediate is preferentially generated.

<MultiModal>![CC1(C([X])C2(C(CCC#C)(C1)C(C/C2=C\[Sn](CCCC)(CCCC)CCCC)O[Si](C)(C)C)O[Si](C)(C)C)C,X is single electron](/media/uploads/7771579e-10b4-4dca-83d6-dd78e25b8647.png)</MultiModal>

<Checkpoint>[Next, the intermediate is preferentially formed: CC1(C([X])C2(C(CCC#C)(C1)C(C/C2=C\[Sn](CCCC)(CCCC)CCCC)O[Si](C)(C)C)O[Si](C)(C)C)C,X is single electron](1)</Checkpoint>

Then, a fast 1,2-rearrangement reaction yields a carbon radical stabilized by n electrons of oxygen.

<Checkpoint>[Then, a fast 1,2-rearrangement reaction yields a carbon radical stabilized by n electrons of oxygen](1)</Checkpoint>

<MultiModal>![CC1(C2C(C(C(CC#C)O[Si](C)(C)C)(C1)CC/C2=C\[Sn](CCCC)(CCCC)CCCC)([X])O[Si](C)(C)C)C,X是单电子](/media/uploads/b84b4844-c2f6-4d22-a759-6d5750e98c5f.png)</MultiModal>

Finally, the obtained product A is

<MultiModal>![CC1(C)[C@@H]2[C@@](C(C[C@@H]3O)=C)(O)[C@]3(C1)CCC2=C](/media/uploads/8dc8b141-0a15-47c4-9ae4-9648abafe1d5.png)</MultiModal>
在 $\gamma$ 位引入 $-OTMS$ 吸电子基团的碳自由基相对较为不稳定

<Checkpoint>[在 $\gamma$ 位引入 $-OTMS$ 吸电子基团的碳自由基相对较为不稳定](1)</Checkpoint>

首先形成中间体

<MultiModal>![C#CCCC1(CC(C)(C=C1O[Si](C)(C)C)C)C(C/C([X])=C/[Sn](CCCC)(CCCC)CCCC)O[Si](C)(C)C,X为单电子](/media/uploads/cbc02d9d-b0a7-42a6-9c7a-4b7156b3d641.png)</MultiModal>

<Checkpoint>[首先形成中间体：C#CCCC1(CC(C)(C=C1O[Si](C)(C)C)C)C(C/C([X])=C/[Sn](CCCC)(CCCC)CCCC)O[Si](C)(C)C,X为单电子](1)</Checkpoint>

5-exo-trig的反应速率较快

<Checkpoint>[5-exo-trig的反应速率较快](1)</Checkpoint>

因此优先生成中间体

<MultiModal>![CC1(C([X])C2(C(CCC#C)(C1)C(C/C2=C\[Sn](CCCC)(CCCC)CCCC)O[Si](C)(C)C)O[Si](C)(C)C)C,X是单电子](/media/uploads/7771579e-10b4-4dca-83d6-dd78e25b8647.png)</MultiModal>

<Checkpoint>[接下来优先形成中间体：CC1(C([X])C2(C(CCC#C)(C1)C(C/C2=C\[Sn](CCCC)(CCCC)CCCC)O[Si](C)(C)C)O[Si](C)(C)C)C,X是单电子](1)</Checkpoint>

然后再经过一步快速的1,2重排反应得到被氧的n电子稳定的碳自由基

<Checkpoint>[然后再经过一步快速的1,2重排反应得到被氧的n电子稳定的碳自由基](1)</Checkpoint>

<MultiModal>![CC1(C2C(C(C(CC#C)O[Si](C)(C)C)(C1)CC/C2=C\[Sn](CCCC)(CCCC)CCCC)([X])O[Si](C)(C)C)C,X是单电子](/media/uploads/b84b4844-c2f6-4d22-a759-6d5750e98c5f.png)</MultiModal>

最后经得到的产物A为

<MultiModal>![CC1(C)[C@@H]2[C@@](C(C[C@@H]3O)=C)(O)[C@]3(C1)CCC2=C](/media/uploads/8dc8b141-0a15-47c4-9ae4-9648abafe1d5.png)</MultiModal>