1. Using dashed lines to represent the intermolecular interactions, draw, name, and include partial charges (if any) for the strongest intermolecular attraction that occurs between silica gel and the following molecules: silica gel representation HO OH Si O J www. O ...... a. (i) methyl salicylate OH Silica gel has a polymeric structure; use the structure provided above to represent silica gel for this question. provided to answer the following questions. 2. Classify a 95% ethyl acetate/hexane solvent system as polar or non-polar, and explain how it helps to move 9-fluorenone (ii, above) up a TLC plate. HO I (ii) 9-fluorenone 3. A reaction was reported in which compound I was converted into compound II (structures shown below), and the reaction progress was monitored by TLC using a 1:1 hexanes:EtOAc solvent system (Org. Lett. 2006, 8, 4125-4128.). Use the information BP O O (iii) isopropylbenzene dyl II The reported Ry values for the compounds were 0.44 and 0.80. Use the structures to determine which compound is expected to be more polar, and match each compound to its respective Ry value. b. Given that the measured distance traveled by the solvent front for each TLC plate was 5.0 cm, calculate the distance traveled by compounds I and II on the TLC plate. Be sure to show your work! c. Briefly describe how the Ry values for compounds I and II would change if the TLC solvent system was changed to (i) 4:1 hexanes:EtOAc; (ii) 1:1 hexanes:EtOH.

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1. Using dashed lines to represent the intermolecular interactions, draw, name, and include
partial charges (if any) for the strongest intermolecular attraction that occurs between
silica gel and the following molecules:
silica gel
representation
HO OH
Si
O O
!.. ......
(i) methyl salicylate
a.
O
Silica gel has a polymeric structure; use the structure provided above to represent silica
gel for this question.
OH
2. Classify a 95% ethyl acetate/hexane solvent system as polar or non-polar, and explain
how it helps to move 9-fluorenone (ii, above) up a TLC plate.
provided to answer the following questions.
HO
I
3. A reaction was reported in which compound I was converted into compound II
(structures shown below), and the reaction progress was monitored by TLC using a 1:1
hexanes:EtOAc solvent system (Org. Lett. 2006, 8, 4125-4128.). Use the information
Be
O
(ii) 9-fluorenone
(iii) isopropylbenzene
dy
II
The reported Ry values for the compounds were 0.44 and 0.80. Use the structures to
determine which compound is expected to be more polar, and match each compound
to its respective Ry value.
b. Given that the measured distance traveled by the solvent front for each TLC plate
was 5.0 cm, calculate the distance traveled by compounds I and II on the TLC
plate. Be sure to show your work!
c. Briefly describe how the Ry values for compounds I and II would change if the TLC
solvent system was changed to (i) 4:1 hexanes:EtOAc; (ii) 1:1 hexanes:EtOH.
Transcribed Image Text:1. Using dashed lines to represent the intermolecular interactions, draw, name, and include partial charges (if any) for the strongest intermolecular attraction that occurs between silica gel and the following molecules: silica gel representation HO OH Si O O !.. ...... (i) methyl salicylate a. O Silica gel has a polymeric structure; use the structure provided above to represent silica gel for this question. OH 2. Classify a 95% ethyl acetate/hexane solvent system as polar or non-polar, and explain how it helps to move 9-fluorenone (ii, above) up a TLC plate. provided to answer the following questions. HO I 3. A reaction was reported in which compound I was converted into compound II (structures shown below), and the reaction progress was monitored by TLC using a 1:1 hexanes:EtOAc solvent system (Org. Lett. 2006, 8, 4125-4128.). Use the information Be O (ii) 9-fluorenone (iii) isopropylbenzene dy II The reported Ry values for the compounds were 0.44 and 0.80. Use the structures to determine which compound is expected to be more polar, and match each compound to its respective Ry value. b. Given that the measured distance traveled by the solvent front for each TLC plate was 5.0 cm, calculate the distance traveled by compounds I and II on the TLC plate. Be sure to show your work! c. Briefly describe how the Ry values for compounds I and II would change if the TLC solvent system was changed to (i) 4:1 hexanes:EtOAc; (ii) 1:1 hexanes:EtOH.
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