Experiments show that the photo-induced reaction of 1,3-dimethyladamantane with $\mathrm { B r } _ { 2 }$ yields only one monobrominated product (stereoisomers not considered). Select the option containing all correct statements.
1. Theoretically, if stereoisomers are considered, there are a total of 8 monobrominated products
2. Theoretically, there are 5 monobrominated products that possess enantiomers
3. The experimentally obtained monobrominated product possesses enantiomers
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实验表明，图示烷烃与 $\mathrm { B r } _ { 2 }$ 光照反应，仅检测到1种单溴代产物（不考虑立体异构）。选出包含所有正确说法的选项。
<MultiModal>![C[C@@]12C[C@H]3C[C@](C1)(C)C[C@@H](C2)C3](/media/uploads/c0abd07d-972b-4095-9067-915a3ed97f3a.png)</MultiModal>
1. 理论上，若考虑立体异构，共有8种单溴代物
2. 理论上能得到的单溴代物中有5个具有对映异构体
3. 实验得到的单溴代物有对映异构体
1,2,3
1,2
1,3
2,3
1
2
3
All of the above statements are incorrect.
1,2,3
1,2
1,3
2,3
1
2
3
上述说法均不对
First, analyze all possible monobrominated products of the alkane, considering stereoisomers. There are 8 kinds of monobrominated products as follows, statement 1 is correct.
<MultiModal>![First row from left to right: C[C@@]1(C[C@@]2(CBr)C3)C[C@H]3C[C@H](C2)C1，C[C@@]12C[C@H]3C[C@](C1([H])Br)(C)C[C@@H](C2)C3，C[C@@]12[C@@](Br)([H])[C@H]3C[C@](C1)(C)C[C@@H](C2)C3，C[C@@]12C[C@H]3C[C@](C1)(C)C[C@@H](C2([H])Br)C3；Second row from left to right: C[C@@]12[C@](Br)([H])[C@H]3C[C@](C1)(C)C[C@@H](C2)C3，C[C@@]12C[C@H]3C[C@](C1)(C)C[C@@H](C2([H])Br)C3，C[C@@]12C[C@@]3(Br)C[C@](C1)(C)C[C@@H](C2)C3，C[C@@]12C[C@H]3C[C@](C1)(C)C[C@@H](C2)C3([H])Br](/media/uploads/8faadc38-4fe0-4c78-8157-dd2a76de0bb2.png)</MultiModal>

<Checkpoint>[There are 8 kinds of monobrominated products, statement 1 is correct](1)</Checkpoint>

The following 4 monobrominated products do not have a mirror plane and have enantiomers, statement 2 is incorrect.
<MultiModal>![C[C@@]12[C@@](Br)([H])[C@H]3C[C@](C1)(C)C[C@@H](C2)C3，C[C@@]12C[C@H]3C[C@](C1)(C)C[C@@H](C2([H])Br)C3，C[C@@]12[C@](Br)([H])[C@H]3C[C@](C1)(C)C[C@@H](C2)C3，C[C@@]12C[C@H]3C[C@](C1)(C)C[C@@H](C2([H])Br)C3](/media/uploads/dd997e4a-61f5-49d3-845a-74b5c07838fd.png)</MultiModal>

<Checkpoint>[There are 4 monobrominated products with enantiomers, statement 2 is incorrect](1)</Checkpoint>

The only monobrominated product obtained is generated from the most stable free radical. The free radical should be a tertiary free radical, and the product is as follows. It has a mirror plane and no enantiomers, statement 3 is incorrect.
<MultiModal>![C[C@@]12C[C@@]3(Br)C[C@](C1)(C)C[C@@H](C2)C3](/media/uploads/ca289c19-ce8a-4cc1-8682-a197b80f8c70.png)</MultiModal>

<Checkpoint>[The experimentally obtained monobrominated product is generated from a tertiary free radical](0.5)</Checkpoint>

<Checkpoint>[The experimentally obtained monobrominated product has no enantiomers](0.5)</Checkpoint>

The answer is option E.
先分析该烷烃所有可能的单溴代物，考虑立体异构，共有如下8种单溴代物，说法1正确。
<MultiModal>![第一排从左至右依次为C[C@@]1(C[C@@]2(CBr)C3)C[C@H]3C[C@H](C2)C1，C[C@@]12C[C@H]3C[C@](C1([H])Br)(C)C[C@@H](C2)C3，C[C@@]12[C@@](Br)([H])[C@H]3C[C@](C1)(C)C[C@@H](C2)C3，C[C@@]12C[C@H]3C[C@](C1)(C)C[C@@H](C2([H])Br)C3；第二排从左至右依次为C[C@@]12[C@](Br)([H])[C@H]3C[C@](C1)(C)C[C@@H](C2)C3，C[C@@]12C[C@H]3C[C@](C1)(C)C[C@@H](C2([H])Br)C3，C[C@@]12C[C@@]3(Br)C[C@](C1)(C)C[C@@H](C2)C3，C[C@@]12C[C@H]3C[C@](C1)(C)C[C@@H](C2)C3([H])Br](/media/uploads/8faadc38-4fe0-4c78-8157-dd2a76de0bb2.png)</MultiModal>

<Checkpoint>[共有8种单溴代物，说法1正确](1)</Checkpoint>

单溴代物中如下4种没有镜面，有对映异构体，说法2错误。
<MultiModal>![C[C@@]12[C@@](Br)([H])[C@H]3C[C@](C1)(C)C[C@@H](C2)C3，C[C@@]12C[C@H]3C[C@](C1)(C)C[C@@H](C2([H])Br)C3，C[C@@]12[C@](Br)([H])[C@H]3C[C@](C1)(C)C[C@@H](C2)C3，C[C@@]12C[C@H]3C[C@](C1)(C)C[C@@H](C2([H])Br)C3](/media/uploads/dd997e4a-61f5-49d3-845a-74b5c07838fd.png)</MultiModal>

<Checkpoint>[单溴代物中有4个具有对映异构体，说法2错误](1)</Checkpoint>

得到的唯一单溴代物，由最稳定的自由基生成，该自由基应为三级自由基，产物如下。其存在镜面，没有对映异构体，说法3错误。
<MultiModal>![C[C@@]12C[C@@]3(Br)C[C@](C1)(C)C[C@@H](C2)C3](/media/uploads/ca289c19-ce8a-4cc1-8682-a197b80f8c70.png)</MultiModal>

<Checkpoint>[实验得到的单溴代物由三级自由基生成](0.5)</Checkpoint>

<Checkpoint>[实验得到的单溴代物没有对映异构体](0.5)</Checkpoint>

答案为E选项