Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
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
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
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...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Select the reagents you would use to synthesize the compound below from benzene. (More than one step is required. If no third step is needed, choose (none).) Reagents Available a. Br2, FeBra f. KMNO4. H20 b. Clz, FeCl, g. Hz. Pd/C c. HNO,, H,SO, h. SOg, H,SO, d. CH,CI, AICI, i. NaOH, H2O e. CH,COCI, AICI, j. N-bromosuccinimide (NBS) ball & stick v-+ labels Step 1: Step 2: Step 3:arrow_forward4. Predict the major product for the following reactions. 1. SOCI₂, pyr 2. PhMgBr 3. H a. b. C. d. e. f. 9. NH₂ NH₂ OTS CI 1. H3O*, heat 2. SOCI₂, pyr 1. HNO3, H₂SO4 2. H₂, Pt NH₂ 3. NaNO₂, HCI 4. CuCN 5. H3O*, heat 1. Br₂, FeBr3 2. SOCI₂, pyr. 1. 2 2. xs LAH 3. H₂O 1. HBr, ether 2. NaCN 3. PhMgBr 4. H* 1. NaCN 2. LiAlH4 (xs) 3. H₂O 4. NH₂arrow_forward6. Predict the product for the following reaction. "NH₂ Br H₂N NO₂ D. H₂O* A. Fe/HCI IV OH OH Br 11 NH₂ "NH₂ H₂N A. IB. II C. III D. IV E. V 7. Provide the reagents necessary to carry out the following reaction. NH₂ V 1. LIAIH4 2. H₂O NH₂ B. H₂CCOCI C. Br₂/FeBr3 E. dil. Na₂CO3 IIIarrow_forward
- 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_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_forward
- Predict 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_forwardFrom 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_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
- 12. Give the major organic product(s) of the following reactions or sequences of reactions. a) b) c) COOH CH3 + H3C- OH CH3 1. LIAIH4, ether 2. H3O+ H 1. NaBH4, ethanol 2. H3O+ + NaHarrow_forwardIn which compound is the halogen substituted most rapidly by aq hydroxide ions? a. CH3CH2CH2CH2Cl b. (CH3)3CI c. (CH3)3CCl d. CH3CH2CH2CH2Iarrow_forwardWhich is the main reduction product of the following compound with LIAIH4 in ether followed by an aqueous workup? i. LIAIH4/ether ? `NM22 ii. H+ OH NME2 A. ОН ОН `NMe2 о но NME2 С. OH `NM22 D. B.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY