Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 14.15, Problem 14.28P
Give the expected products of the following reactions. Include a protonation step where necessary.
- a. 2,2 dimethyloxirane + isopropylmagnesium bromide
- b. propylene oxide+n-butyllithium
- c. cyclopentyloxirane + ethyllithium
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6. Provide the structure for the major product in the following reactions.
b.
P
f.
OH
g.
Lia
*
Oia
ملی
CI
1. SOCI₂, pyr.
2.
to
Br
2
1. LIAIH4 (xs)
2. H₂O
1. LIAI(OR) 3H
2. H₂O
2.
NH₂
Et₂CuLi
1. EtMgBr (xs)
2. H₂O
1. Mg
2. CO₂
3. H*
4. SOCI₂, pyr
1. [H], NaBH3CN, EtNH₂
CI
pyridine
Which option is the major product expected for the reaction below?
a.
b.
C.
d.
CHO
NaOH (trace)
H₂O
o
HO
OH
OH
OH
CHO
or
?
Starting Materials
CH3B
CH3CH2BR
CH3CH2CH,Br
C6H5Br
Reagents
Mg, ether
1.
a.
2.
13CH2-13C-OH
b.
13CO2 then H3O*
3.
LIAIH4 then H3o*
PBr3
CO2 then H30*
C.
4.
d.
5.
C6HsCH2Br
е.
Select a starting material and a series of reagents necessary to synthesize this compound in as few steps as possible.
Enter your selection as a number for the starting material, followed by the letters of the reagents, in the order that you wish to use them, i.e. 3abcf.
Chapter 14 Solutions
Organic Chemistry (9th Edition)
Ch. 14.2C - Rank the given solvents in decreasing order of...Ch. 14.2D - Prob. 14.2PCh. 14.2D - In the presence of 18-crown-6, potassium...Ch. 14.3B - Give a common name (when possible) and a...Ch. 14.3C - Prob. 14.5PCh. 14.3C - Name the following heterocyclic ethers.Ch. 14.4 - Propose a fragmentation to account for each...Ch. 14.5 - Prob. 14.8PCh. 14.5 - Prob. 14.9PCh. 14.6 - Prob. 14.10P
Ch. 14.7 - Explain why bimolecular condensation is a poor...Ch. 14.7 - Prob. 14.12PCh. 14.7 - Prob. 14.13PCh. 14.8 - Prob. 14.14PCh. 14.8 - Prob. 14.15PCh. 14.8 - Prob. 14.16PCh. 14.10A - Prob. 14.17PCh. 14.10A - Prob. 14.18PCh. 14.10B - Prob. 14.19PCh. 14.11B - Show how you would accomplish the following...Ch. 14.11B - Prob. 14.21PCh. 14.12 - Prob. 14.22PCh. 14.12 - Prob. 14.23PCh. 14.12 - Prob. 14.24PCh. 14.13 - Prob. 14.25PCh. 14.13 - Prob. 14.26PCh. 14.14 - Prob. 14.27PCh. 14.15 - Give the expected products of the following...Ch. 14 - Write structural formulas for the following...Ch. 14 - Give common names for the following compounds. a....Ch. 14 - Give IUPAC names for the following compounds. a....Ch. 14 - Glycerol (propane-1,2,3-triol) is a viscous syrup...Ch. 14 - Prob. 14.33SPCh. 14 - Show how you would make the following ethers,...Ch. 14 - (A true story.) An inexperienced graduate student...Ch. 14 - Prob. 14.36SPCh. 14 - a. Show how you would synthesize the pure (R)...Ch. 14 - a. Predict the values of m/z and the structures of...Ch. 14 - The following reaction resembles the...Ch. 14 - Prob. 14.40SPCh. 14 - Prob. 14.41SPCh. 14 - Prob. 14.42SPCh. 14 - Give the structures of the intermediates...Ch. 14 - Prob. 14.44SPCh. 14 - Show how you would synthesize the following ethers...Ch. 14 - Prob. 14.46SPCh. 14 - Prob. 14.47SPCh. 14 - Prob. 14.48SPCh. 14 - An acid-catalyzed reaction was carried out using...Ch. 14 - Propylene oxide is a chiral molecule. Hydrolysis...Ch. 14 - Prob. 14.51SPCh. 14 - Prob. 14.52SPCh. 14 - Prob. 14.53SPCh. 14 - Prob. 14.54SPCh. 14 - In 2012, a group led by Professor Masayuki Satake...
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- 2. Predict the products of the following reactions. ez a. b. C. d. 1) LDA, -78 C 2) PhCH₂Br H NaOH, H₂O heat + 1) HNEt₂2, ACOH 2) iPrBr 3) HCI, H₂O HCI H₂Oarrow_forwardSelect the product 1. CH3MGB (excess) OMe 2. H20 OH но OMe А. С. D. C. B.arrow_forwardPredict the products (if any) of the reaction of each of the ff. reagents with benzoic acid. a. NaBH 4b. H2, Pt, 1 atm, room temp.c. SOCl2d. conc. HCle. CH3OHarrow_forward
- From the table of reagents shown below, show how you synthesize the product from the given reactant. OCH₂CH3 OH a. NBS, (PhCO₂)2 b. Br2, FeBr3 c. Br₂, H+ d. OH e. NaOH(s), A f. HNO3, H₂SO4 g. H₂ CrO4 Reagents available h. CH3 CI, AICI, o. CuCN i. CH3 CH₂ Br p. H₂O+, A j. CH₂O, A q. CH3 CH₂ COCI, AICI, k. CH3COCI, AICI3 r. H₂NNH₂, OH, A 1. Mg, Et₂ O s. H₂, Pd/C m. CO₂ (s) then H3O+ t. H₂PO₂ n. HONO 0°C u. Cl₂, FeCl3 (Enter the letter(s) of the reagent(s) needed in the box, in the order that they must be used. No more than two steps are required to perform the synthesis. Note that a retrosynthetic arrow is used, and therefore the reactant is shown on the right.) Answer:arrow_forwarde. f. g. d. 5. Provide the structure for the major product in the following reactions. or a. b. OH 6 6 3 6 Br 1. SOCI₂, pyr. 2. 2. 2 t 1. LiAlH4 (xs) 2. H₂O 1. LIAI(OR) 3H 2. H₂O Et₂CuLi NH₂ 1. EtMgBr (xs) 2. H₂O 1. Mg 2. CO2 3. H* 4. SOCI₂, pyr 1. [H], NaBH3CN, EtNH2 O CI pyridinearrow_forwardselect reagents: cyclopentanone Reagents a. C6H5CHO b. NaOH, ethanol c. Pyrrolidine, cat. Hj. d. H₂C=CHCN e. H3O+ f. LDA g. A) bg EtOC(=O)CO₂Et h. i. B) ka k. I. m. O: BrCH₂CH=CH₂ NatOEt, ethanol Br₂, H+ K+ t-BUO™ CH2(CO2Et)z heat C) jh CO₂Et D) Imarrow_forward
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