This topic contains a solution. Click here to go to the answer

Author Question: When a student ran an asymmetric dihydroxylation reaction using cis-stilbene and the ligand ... (Read 69 times)

Pea0909berry

  • Hero Member
  • *****
  • Posts: 573
When a student ran an asymmetric dihydroxylation reaction using cis-stilbene and the ligand (DHQ)2PHAL, the hydrobenzoin showed an optical rotation of 0. Explain this result.

Question 2

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 />"

Question 3

A student proposed the synthesis shown in Equation PE 14.5.
  After extraction and recrystallization, a white, flaky, crystalline product was obtained that had a melting point of 117119C. The desired product, shown in Equation PE14.5, has a melting point of 152154C. Write the structure of the compound that the student isolated and briefly explain what happened. Write a rational arrow-pushing mechanism for the formation of this product. Hint: If you were actually doing this reaction, you would have prepared a prelab writeup that included all of the physical constants for your starting materials.

Question 4

Propose three different syntheses of the alcohol shown below starting with a ketone and a Grignard reagent. In all cases, first show how you would make the Grignard reagent.
   
 

Question 5

ecmC4w4AfLpTEBHAiwwdITJWTEBIwmQEHjhhRfwyG5dsffJJ+GaNa64iyPTq3POPUeaYpFJllYoXKXcbkcdiSf1tqDL9U7c5XIGzSNQ4fTNImgIC+GZJwWA3alEeapCh4wwZUGx6F3zCgpztFsJVSvKsueXYI0qW091GTp8plFUl8IK1Zdh8uPdAQIsMAIs4t3SEhg0y/re++/Fm7Vu55NpKb3D1emll1ZIc1P1Pt5mAqlOgAVGqt9Brn/GEaCZhDmOOXIm4eLRF+OWLVuazYBMrXJypkvTKzLB+umnnzTzcLvdOHjwIOx0UEd87PHHdJ050SyQd5qUQC0WZnuFjCJobHY72qxeB3BlX25xU47gJr28JFaLBYZ+8LUEBr0ryZyTzDrJvDPZid7fJSVvBFWDBUYQDv6QJgRYYKTJjeTLyDwC3377LY6fME42nnfccXtUvhBkWkVCgUytSDiQgNBKat+P6dOn4W+//aZ1GO/LKAINWOFyol01W6EIC1t2HpZWxm+OlVE4fRfLAkO/u64lMCj3yspKadZJ5p0kOKiTb6bEAsNMd4ProhcBXgdDtJCcmEAqExDT/3DjjTPgxx9/hPnzFoDdbof/+7//07yk2bNnwfLC5ZB370IYPXo07LXXXkHHiVC08PAjD8PcufdA//4D4IFFD8Dxxx8fdAx/YAK7dmyH2voGAaIlZHXoBFmtmEmsBHgdjFjJBZ/3bum7MHLkCOjTpw+8/tob0K5du+ADxKe1a9fAjTfdCL///jvcuyAPxo4d2+gd2Ogkg3eIwRu4fNJlsHHjRvj+ux8MLo2zZwIJJKCXUuF8mAATSB4BChH7zDPP4CFdOuOAAf3xg7IPNCvzxx9/IK3KHZrIz4LW3KC1N4497hh89dVVmo7eoefx58wisGfPHnzyySeDno1ffvkFX375pcwCoePV8gxGfDC3bduGl1x6Ce63fxsUi31KX4bOhxyMTz31FNLzGppoFpcCZdAsLgXOoAAayUi0rpAYzMGOnQ5Eq/VMfPfdd5NRDS6TCRhGgE2kDEPLGTOBxBMgATFz5q3SbOqyyyfiDz/80GQlvvjiCxwxcoR09L5/0f2ajt5NZsIHZAQBMp2jDrE6GABFICPnf06xEWCBERu3uro6FDOyUlhcOu4SrKqqkhnRYEthYSEefsRh2O+Uvli6vlSzAPJDo9Dfrdu0wiuvmhLWD03z5Dh3vv32W9jLciJ273GUFOc0wMOJCaQbARYY6XZH+XqYgCDw9ddf46gLR2FW2/1x7ry5+NdffzXiQn4V5OhNC+qRozd1HjkxgUgEWGBEohPbdywwmseNBMSyZcuaFBDhBEhoaRUVFXjueefKAZa8hXlB4jn02Hg/03vZNsqGbdtl4fwF8zVnk+Mtg89nAmYhwALDLHeC68EEDCCwevXbcqTsqO7dsKioSJq2KI7eFBkqkqO3AdXhLFOcAAsM/W8gC4zomZLp52mn/Uuagj799NOaJlChualNqO6++y7cuXNn6CHy8xtvvI7Hn9BTrgW0cuUrQWaAmic0Y6d6ZnnS5Muxurq6GWfzoUwgNQmwwEjN+8a1ZgJREyBB8cijj0hbXzIZoAX1KA47ranBU/NRY+QDBQEWGPo/BiwwmmZKpp5k8knhZm+7bSZSh725ad2767BP35PxiK6H43PPPaf57vv777/xwYcexA4HtkeKSFVerqwt09zSvMeTDwgJIfKNI2FUtsG3GGZs2fFZTCClCHAUqQQ61HNRTCCZBGS0kssvgw4dOkBBwRJo06ZNMqvDZacgAeHQDYcdfijsrPsT9t13X3kFYuQXbr/jdvjs040peEXJrzJHkQp/D0RACnjgwQcgL+9eGDbsLFiYtxB69OgR/oQmvhHmVeB0OmHW7Dvh6B5Hw6IHHoBT+p3S6Kzt27eDmO0A51InXDH5CrE9Bzp27NjouEg7lOh+QpTDgvn3wrhx48JG94uUD3/HBFKWQErJIa4sE2ACTIAJJI0Az2Dojz7RMxiecqdc+d1CK8Bb87Am3CXVV2COb5V4S04xNo49F+7EkP2eSnTm2mWZoqMU+GuxYV5RGXpCDqePNLNKJp1k2mk5qReSqaeeaceOHXjzzTdJB+8rpkxGEeJbM3sROhaHDhuKB3bsgPmL85EiPzWVaH2iceMvlc7ns2bdieQLwokJZCIBNpHKxLvO18wEmAATiIEAC4wYoDVxSuIFRkGgky86/EWV2tKhtiwvcJy1AGNZRtFTXoTWIFFhRZvNGsiXvrM4sLIhAIkWxTvzzMFIPmKPPvYokomnUWnz5s143vnnYbsD2mI4B28SO6+88jIefUwPpCh74RL5dpCPBy3mN2bsGNy6dWu4Q3k/E8gIAiwwMuI280UyASbABOInwAIjfoahOSRbYNgK3KFVEp8bsDjHEhACtgLNmQaNEwO7aktV4sKOxeXVIldfaqjFskJHIP/sIv8Micv1jpxdoCh3iUolJW9IB28SEeEcvCl6lZbYIQHyn//8B7seeQSe3Kc3rlu3NlHV5nKYgKkJsA9Gyhq3ccWZABNgAoklwD4Y+vNOtA9G3aYl0NZydeBCLA6o3jgLugT2AOz6BCa27gvLlX22AvCsnApZymfxd8eWTbDhi22wW2zv374bnPKvXpDVInDA+oVDYNDMtWJHDlTUPwjHaaz2/uOae+DQobPlSQXlHpjaS11CIK9EbAnxAI89/hg4HHPEauB94YFFD0CvXr0iFi0W6YMbZ8yAr7/5Gu65Z67019h7770jnsNfMoGMIWBq+cOVYwJMgAkwAdMQ4BkM/W9F0mYwbNlot3p9IgpDzKRqXN7ZBbsjD+1kxhQ0g1GDhbkhZk7SDErMUlT6PCrq3d7zxH6HK6yXh4BZ758psTq0F8TTn3jkHGtqavDaa6+R6wNdf/11+OuvvzY64aeffsIpV14hfThuuulGJJ8OTkyACQQTYBOpYB78iQkwASbABMIQYIERBkwcu5MmMLKdWOLMlmZKtny1mVQ9FmWT8LAKs6ZSzA4SGA1Y4jedsqDDWYxlpSXosHmFCoANy0hjeNxok6LDhm5tFw8/saqiHK+plDU/Jj8Pf0Y6b3z22Wc4ZOgQGd578cOLpYM3rWC/8L6F0meDfDdokT5OTIAJaBP4fwAAAP//8qKw5wAAP09JREFU7Z0LfFTF+f4fKkGiBgsYingBDVbAsii0Bi+oG9SCWpdaUEsWJV4C3kJABYOCGlQM91BtA15CJaGtQSXYGrRN6D/YGn4ahEQJSsCgBmuiiSZoIkk7/5mzl+yScza7ye5md/Oczyfu2TlzZt75zsqZ58y870DwIAESIAESIAEvCPznP/8RvaOOE83Nzc7cf/vbX8WY803O7zzxjYDiqf6CdTSUZQkAApZcUVOdbzs3pYtqhwENJcKirpuzRF1ThbBqebNEg7zeUmXPD7MoqGpx3CE/G0Ruskkry5pdIZrKsm3lwipKm1yy6Zw681psdehk6bak//3vf+LVV18RccPP1v6GDjtTjDpvpHjjjb91m02smATChUAvZaj8x4YHCZAACZAACXgk8OWXX+L0M07DkcbvcPzxx2t55WALCx9eiN3v7/F4Ly/qE4jq01u70HK0VT+Dn1Mby9ehn2k2YM5GU5EFa8cMwIIyILeyCdPj+uLwtoU4bfJSWHMrsXH695jSy4R8SxYatswCHPfCisKKxzCk5Xu0SPuiTjgBVZtuwOTFsiBLNmpWnoRBw6fJK6mobFmNOFsTdVvitMdeR4xuru5NlIIa9953j/zN98Wa1WsQFRXVvQaxdhIIAwIUGGHQSTSRBEiABEKBAAWG/3uh+wRGlhQYs7B/3QyYZufAklmKLSkmbJoRhcQcEwqq92DSgF2YET0OOfbBf9UGmTcpxzMEUybq3



Related Topics

Need homework help now?

Ask unlimited questions for free

Ask a Question
Marked as best answer by a Subject Expert

Chou

  • Sr. Member
  • ****
  • Posts: 335
Answer to Question 1

The resulting diol is a meso compound and is therefore achiral, which means it must have an optical rotation of 0.

Answer to Question 2



Answer to Question 3

The product that the student obtained was 4-hydroxybenzaldehyde. This occurred because the Grignard reagent, being a strong base, deprotonated the hydroxy group in the aldehyde, resulting in the formation of benzene and the phenoxide shown below. Protonation of the phenoxide gave the aldehyde back.


Answer to Question 4






 

Did you know?

The most common childhood diseases include croup, chickenpox, ear infections, flu, pneumonia, ringworm, respiratory syncytial virus, scabies, head lice, and asthma.

Did you know?

Signs and symptoms that may signify an eye tumor include general blurred vision, bulging eye(s), double vision, a sensation of a foreign body in the eye(s), iris defects, limited ability to move the eyelid(s), limited ability to move the eye(s), pain or discomfort in or around the eyes or eyelids, red or pink eyes, white or cloud spots on the eye(s), colored spots on the eyelid(s), swelling around the eyes, swollen eyelid(s), and general vision loss.

Did you know?

The longest a person has survived after a heart transplant is 24 years.

Did you know?

Allergies play a major part in the health of children. The most prevalent childhood allergies are milk, egg, soy, wheat, peanuts, tree nuts, and seafood.

Did you know?

The most destructive flu epidemic of all times in recorded history occurred in 1918, with approximately 20 million deaths worldwide.

For a complete list of videos, visit our video library