Draw the structure of a molecule, an unknown aldehyde or ketone listed in the tables, that would show a negative Tollens’ test and a negative iodoform test. There is more than one correct answer. Draw one!

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter11: Ethers, Epoxides, And Sulfides
Section: Chapter Questions
Problem 11.38P
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Draw the structure of a molecule, an unknown aldehyde or ketone listed in the tables, that would show a negative Tollens’ test and a negative iodoform test. There is more than one correct answer. Draw one!

 

(please help solve this question but also explain it!)

 

comparison, the Tollens' test is relatively safe, though as noted, hydroxide is caustic. Wash hands
with plenty of water if exposed. If you spill silver (I) on your skin, it will stain a dark brown. The
stain may take 1-2 hours to appear and can last for a day.
J
A
Table 1 - Aldehydes
bp
mp (°C)
(C) semicarbazone
compound
bp
(C)
Glyoxal 50
Acrolein 52
Trimethylacetaldehyde 75
2-methylbutanal 93
Chloral 98
Crotonaldehyde 104
MOD
Adol
Table 2- Ketones
mp (°C)
semicarbazone
270 UN
171
190
compound
acetone
PAX
103
22
compound
90
199
Hexanal 1319106
Heptanal 156
Furfural 161
3-cyclohexene-1-
165
carboxaldehyde
Benzaldehyde 17
Phenylacetaldehyde 194
c
bp (°C) mp semicarbazone (°C)
56
190
3-pentanone 102
139
2-pentanone 102
112
pinacolone 106
158
chloracetone 119
164
2,4-dimethyl-3-pentanone 125
160
2-hexanone 129
122
4-methyl-3-penten-2-one 130
164
cyclopentanone 131
203
4-heptanone 145
133
5-methyl-2-hexanone 145
147
3-heptanone 148
103
2-heptanone 151
127
cyclohexanone 156
167
6-methyl-3-heptanone 160
132
5-methyl-3-heptanone
160
102
2-octanone
173
123
You will want to look up structure of these unknowns aldehydes and ketones
%
109
2027272727
155
222
156
wy N
for N
Transcribed Image Text:comparison, the Tollens' test is relatively safe, though as noted, hydroxide is caustic. Wash hands with plenty of water if exposed. If you spill silver (I) on your skin, it will stain a dark brown. The stain may take 1-2 hours to appear and can last for a day. J A Table 1 - Aldehydes bp mp (°C) (C) semicarbazone compound bp (C) Glyoxal 50 Acrolein 52 Trimethylacetaldehyde 75 2-methylbutanal 93 Chloral 98 Crotonaldehyde 104 MOD Adol Table 2- Ketones mp (°C) semicarbazone 270 UN 171 190 compound acetone PAX 103 22 compound 90 199 Hexanal 1319106 Heptanal 156 Furfural 161 3-cyclohexene-1- 165 carboxaldehyde Benzaldehyde 17 Phenylacetaldehyde 194 c bp (°C) mp semicarbazone (°C) 56 190 3-pentanone 102 139 2-pentanone 102 112 pinacolone 106 158 chloracetone 119 164 2,4-dimethyl-3-pentanone 125 160 2-hexanone 129 122 4-methyl-3-penten-2-one 130 164 cyclopentanone 131 203 4-heptanone 145 133 5-methyl-2-hexanone 145 147 3-heptanone 148 103 2-heptanone 151 127 cyclohexanone 156 167 6-methyl-3-heptanone 160 132 5-methyl-3-heptanone 160 102 2-octanone 173 123 You will want to look up structure of these unknowns aldehydes and ketones % 109 2027272727 155 222 156 wy N for N
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