Concept explainers
(a)
Interpretation:
How the given compound with specified stereochemistry can be produced from an
Concept introduction:
A cyclopropyl group can be introduced in a compound by reacting the corresponding alkene (or
The stereochemistry of the double bond is preserved in the reaction as it is a concerted addition. If the alkene has a cis configuration, the two similar substituents on the double bond end up on the same side of the cyclopropyl ring in the product. If it is a trans alkene, the similar substituents on the double bond end up on opposite sides of the ring in the product.
Carbenes are generated in situ, typically by irradiating a mixture of the alkene and diazomethane with UV light or by treating a mixture of the alkene and haloform (trihalomethane) with a strong base like an alkoxide.
(b)
Interpretation:
How the given compound with specified stereochemistry can be produced from an alkene is to be shown along with the reagents used and special conditions if any.
Concept introduction:
A cyclopropyl group can be introduced in a compound by reacting the corresponding alkene (or alkyne) with a carbene. A carbene is a species with only two groups, typically hydrogen or halogen atoms bonded to a carbon. The carbon atom also carries a lone pair of electrons or sometimes two unpaired electrons. This pair of electrons makes the carbene extremely reactive. Carbenes add to an alkene or alkyne by simultaneously forming bonds with the two carbon atoms from the double (or triple) bond. One bond is formed by the lone pair on the carbene and the other by the
The stereochemistry of the double bond is preserved in the reaction as it is a concerted addition. If the alkene has a cis configuration, the two similar substituents on the double bond end up on the same side of the cyclopropyl ring in the product. If it is a trans alkene, the similar substituents on the double bond end up on opposite sides of the ring in the product.
Carbenes are generated in situ, typically by irradiating a mixture of the alkene and diazomethane with UV light or by treating a mixture of the alkene and haloform (trihalomethane) with a strong base like an alkoxide.
(c)
Interpretation:
How the given compound with specified stereochemistry can be produced from an alkene is to be shown along with the reagents used and special conditions if any.
Concept introduction:
A cyclopropyl group can be introduced in a compound by reacting the corresponding alkene (or alkyne) with a carbene. A carbene is a species with only two groups, typically hydrogen or halogen atoms bonded to a carbon. The carbon atom also carries a lone pair of electrons or sometimes two unpaired electrons. This pair of electrons makes the carbene extremely reactive. Carbenes add to an alkene or alkyne by simultaneously forming bonds with the two carbon atoms from the double (or triple) bond. One bond is formed by the lone pair on the carbene and the other by the
The stereochemistry of the double bond is preserved in the reaction as it is a concerted addition. If the alkene has a cis configuration, the two similar substituents on the double bond end up on the same side of the cyclopropyl ring in the product. If it is a trans alkene, the similar substituents on the double bond end up on opposite sides of the ring in the product.
Carbenes are generated in situ, typically by irradiating a mixture of the alkene and diazomethane with UV light or by treating a mixture of the alkene and haloform (trihalomethane) with a strong base like an alkoxide.
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Chapter 12 Solutions
ORG CHEM W/ EBOOK & SW5 + STUDY GUIDE
- CS2(g) → CS(g) + S(g) The rate law is Rate = k [CS2] where k = 1.6 × 10-6 s−1. S Calculate the half-life.arrow_forwardThe following is a first order reaction where the rate constant, k, is 6.29 x 10-3 min-*** What is the half-life? C2H4 C2H2 + H2arrow_forwardControl Chart Drawing Assignment The table below provides the number of alignment errors observed during the final inspection of a certain model of airplane. Calculate the central, upper, and lower control limits for the c-chart and draw the chart precisely on the graph sheet provided (based on 3-sigma limits). Your chart should include a line for each of the control limits (UCL, CL, and LCL) and the points for each observation. Number the x-axis 1 through 25 and evenly space the numbering for the y-axis. Connect the points by drawing a line as well. Label each line drawn. Airplane Number Number of alignment errors 201 7 202 6 203 6 204 7 205 4 206 7 207 8 208 12 209 9 210 9 211 8 212 5 213 5 214 9 215 8 216 15 217 6 218 4 219 13 220 7 221 8 222 15 223 6 224 6 225 10arrow_forward
- Collagen is used to date artifacts. It has a rate constant = 1.20 x 10-4 /years. What is the half life of collagen?arrow_forwardיווי 10 20 30 40 50 60 70 3.5 3 2.5 2 1.5 1 [ppm] 3.5 3 2.5 2 1.5 1 6 [ppm] 1 1.5 -2.5 3.5arrow_forward2H2S(g)+3O2(g)→2SO2(g)+2H2O(g) A 1.2mol sample of H2S(g) is combined with excess O2(g), and the reaction goes to completion. Question Which of the following predicts the theoretical yield of SO2(g) from the reaction? Responses 1.2 g Answer A: 1.2 grams A 41 g Answer B: 41 grams B 77 g Answer C: 77 grams C 154 g Answer D: 154 grams Darrow_forward
- Part VII. Below are the 'HNMR, 13 C-NMR, COSY 2D- NMR, and HSQC 2D-NMR (similar with HETCOR but axes are reversed) spectra of an organic compound with molecular formula C6H1003 - Assign chemical shift values to the H and c atoms of the compound. Find the structure. Show complete solutions. Predicted 1H NMR Spectrum 4.7 4.6 4.5 4.4 4.3 4.2 4.1 4.0 3.9 3.8 3.7 3.6 3.5 3.4 3.3 3.2 3.1 3.0 2.9 2.8 2.7 2.6 2.5 2.4 2.3 2.2 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4 1.3 1.2 1.1 f1 (ppm) Predicted 13C NMR Spectrum 100 f1 (ppm) 30 220 210 200 190 180 170 160 150 140 130 120 110 90 80 70 -26 60 50 40 46 30 20 115 10 1.0 0.9 0.8 0 -10arrow_forwardQ: Arrange BCC and Fec metals, in sequence from the Fable (Dr. R's slides) and Calculate Volume and Density. Aa BCC V 52 5 SFCCarrow_forwardNonearrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
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