由于A分子中C、H、O三种元素的质量比为6:1:4可知C、H、O的物质的量之比为2:4:1;又由于A的质谱图中质荷比最大值为88,所以A的分子式为C
4H
8O
2,根据分子式可知A中有一个不饱和度,又不能使Br
2的CCl
4溶液褪色,所以A中存在C=O键,再根据1mol B反应生成了2mol C,结合已知条件可推知A的结构为:
![](https://video.ask-data.xyz/img.php?b=https://iknow-pic.cdn.bcebos.com/94cad1c8a786c917d7c6778bca3d70cf3ac757be?x-bce-process=image%2Fresize%2Cm_lfit%2Cw_600%2Ch_800%2Climit_1%2Fquality%2Cq_85%2Fformat%2Cf_auto)
,这样可以进一步推出B、C、D、E、F的结构简式,它们依次是:
![](https://video.ask-data.xyz/img.php?b=https://iknow-pic.cdn.bcebos.com/3b292df5e0fe99253ac94ce237a85edf8cb171be?x-bce-process=image%2Fresize%2Cm_lfit%2Cw_600%2Ch_800%2Climit_1%2Fquality%2Cq_85%2Fformat%2Cf_auto)
,由于B与HBr发生取代反应生成卤代物,再在NaOH醇溶液中发生消去反应,且H分子中所有碳原子均在一条直线上,所以可以推得G和H的结构分别为:
![](https://video.ask-data.xyz/img.php?b=https://iknow-pic.cdn.bcebos.com/574e9258d109b3de0e8ec0dacfbf6c81800a4c4a?x-bce-process=image%2Fresize%2Cm_lfit%2Cw_600%2Ch_800%2Climit_1%2Fquality%2Cq_85%2Fformat%2Cf_auto)
、
![](https://video.ask-data.xyz/img.php?b=https://iknow-pic.cdn.bcebos.com/b03533fa828ba61e362bed9d4234970a314e59be?x-bce-process=image%2Fresize%2Cm_lfit%2Cw_600%2Ch_800%2Climit_1%2Fquality%2Cq_85%2Fformat%2Cf_auto)
,
(1)比较C和E的结构可知,E中氢原子个数比C中多2个,其它原子没有变化再根据反应条件可知该反应为加成反应,故答案为:加成反应;
(2)由A合成H的总产率应为①,②、③三步反应的产率之积,所以由A合成H的总产率=93.0%×81.0%×88.09%=66.3%,故答案为:66.3%
(3)由于A分子中C、H、O三种元素的质量比为6:1:4可知C、H、O的物质的量之比为2:4:1;又由于A的质谱图中质荷比最大值为88,所以A的分子式为C
4H
8O
2,根据分子式可知A中有一个不饱和度,又不能使Br
2的CCl
4溶液褪色,所以A中存在C=O键,再根据1mol B反应生成了2mol C,结合已知条件可推知A的结构为:
![](https://video.ask-data.xyz/img.php?b=https://iknow-pic.cdn.bcebos.com/94cad1c8a786c917d7c6778bca3d70cf3ac757be?x-bce-process=image%2Fresize%2Cm_lfit%2Cw_600%2Ch_800%2Climit_1%2Fquality%2Cq_85%2Fformat%2Cf_auto)
故答案为:
![](https://video.ask-data.xyz/img.php?b=https://iknow-pic.cdn.bcebos.com/8d5494eef01f3a29aff9f17c9a25bc315c607c4a?x-bce-process=image%2Fresize%2Cm_lfit%2Cw_600%2Ch_800%2Climit_1%2Fquality%2Cq_85%2Fformat%2Cf_auto)
(4)由上面的分析可知,C为乙醛,它与银氨溶液反应的离子方程式为:CH
3CHO+2[Ag(NH
3)
2]
++2OH
- ![](https://video.ask-data.xyz/img.php?b=https://iknow-pic.cdn.bcebos.com/810a19d8bc3eb135a8029209a51ea8d3fc1f44be?x-bce-process=image%2Fresize%2Cm_lfit%2Cw_600%2Ch_800%2Climit_1%2Fquality%2Cq_85%2Fformat%2Cf_auto)
CH
3COO
-+NH
4++2Ag↓+3NH
3+H
2O,
故答案为:CH
3CHO+2[Ag(NH
3)
2]
++2OH
- ![](https://video.ask-data.xyz/img.php?b=https://iknow-pic.cdn.bcebos.com/810a19d8bc3eb135a8029209a51ea8d3fc1f44be?x-bce-process=image%2Fresize%2Cm_lfit%2Cw_600%2Ch_800%2Climit_1%2Fquality%2Cq_85%2Fformat%2Cf_auto)
CH
3COO
-+NH
4++2Ag↓+3NH
3+H
2O;
(5)由于B是2,3-丁二醇,与HBr发生取代反应生成卤代物
![](https://video.ask-data.xyz/img.php?b=https://iknow-pic.cdn.bcebos.com/574e9258d109b3de0e8ec0dacfbf6c81800a4c4a?x-bce-process=image%2Fresize%2Cm_lfit%2Cw_600%2Ch_800%2Climit_1%2Fquality%2Cq_85%2Fformat%2Cf_auto)
,再在NaOH醇溶液中发生消去反应生成H,且H分子中所有碳原子均在一条直线上,所以可以推得G和H的结构,G为
![](https://video.ask-data.xyz/img.php?b=https://iknow-pic.cdn.bcebos.com/574e9258d109b3de0e8ec0dacfbf6c81800a4c4a?x-bce-process=image%2Fresize%2Cm_lfit%2Cw_600%2Ch_800%2Climit_1%2Fquality%2Cq_85%2Fformat%2Cf_auto)
H为
![](https://video.ask-data.xyz/img.php?b=https://iknow-pic.cdn.bcebos.com/b03533fa828ba61e362bed9d4234970a314e59be?x-bce-process=image%2Fresize%2Cm_lfit%2Cw_600%2Ch_800%2Climit_1%2Fquality%2Cq_85%2Fformat%2Cf_auto)
,G转化为H的化学方程式为
![](https://video.ask-data.xyz/img.php?b=https://iknow-pic.cdn.bcebos.com/810a19d8bc3eb135a9f69309a51ea8d3fd1f444a?x-bce-process=image%2Fresize%2Cm_lfit%2Cw_600%2Ch_800%2Climit_1%2Fquality%2Cq_85%2Fformat%2Cf_auto)
,故答案为:
![](https://video.ask-data.xyz/img.php?b=https://iknow-pic.cdn.bcebos.com/810a19d8bc3eb135a9f69309a51ea8d3fd1f444a?x-bce-process=image%2Fresize%2Cm_lfit%2Cw_600%2Ch_800%2Climit_1%2Fquality%2Cq_85%2Fformat%2Cf_auto)
(6)A的结构为:
![](https://video.ask-data.xyz/img.php?b=https://iknow-pic.cdn.bcebos.com/94cad1c8a786c917d7c6778bca3d70cf3ac757be?x-bce-process=image%2Fresize%2Cm_lfit%2Cw_600%2Ch_800%2Climit_1%2Fquality%2Cq_85%2Fformat%2Cf_auto)
,其中有8个氢原子,而X中核磁共振氢谱只有3个峰,所以X是一个非常对称的结构,X中两个氧原子,且1mol X可在HIO
4加热的条件下反应,产物只有1mol Y,结合题目信息,说明X中有两个羟基,合X的不饱和度是1,有四个碳原子,所以X中有由四个碳原子构成的环,由此X的结构可以写成
![](https://video.ask-data.xyz/img.php?b=https://iknow-pic.cdn.bcebos.com/c2cec3fdfc0392456c70c4bd8494a4c27c1e25be?x-bce-process=image%2Fresize%2Cm_lfit%2Cw_600%2Ch_800%2Climit_1%2Fquality%2Cq_85%2Fformat%2Cf_auto)
,故答案为:
![](https://video.ask-data.xyz/img.php?b=https://iknow-pic.cdn.bcebos.com/c2cec3fdfc0392456c70c4bd8494a4c27c1e25be?x-bce-process=image%2Fresize%2Cm_lfit%2Cw_600%2Ch_800%2Climit_1%2Fquality%2Cq_85%2Fformat%2Cf_auto)
.