Which of the following is true of the mechanism of BH3 addition to an alkene?
Select one:
a. BH3 adds to alkene by formation of a strained 3-membered ring intermediate.
b. B-H adds to C=C in a concerted, SYN addition.
c. B-H adds to C=C in a step-wise, SYN addition.
d. B-H attaches to alkene with ANTI stereochemistry.
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Which of the following is true of the mechanism of
BH3 addition to an alkene?
Select...
15) What synthetic goal is achieved by subjecting an alkene to BH3-THF, followed by oxidative working...
15) What synthetic goal is achieved by subjecting an alkene to BH3-THF, followed by oxidative working using H2O2 and NaOH? A) Markovnikov addition of water where relative stereochemistry is preserved B) Markovnikov addition of water where relative stereochemistry is scrambled (or destroyed) C) Anti-Markovnikov addition of water where relative stereochemistry is preserved D) Anti-Markovnikov addition of water where relative stereochemistry is scrambled (or destroyed) 16) Which of the following reaction occur by anti-addition to an alkene? A) Br2 B) BH3-THF,...
REVIEW TOPICS Relerences In each case below select the synthetic procedures that could be used to...
REVIEW TOPICS Relerences In each case below select the synthetic procedures that could be used to carry out the transformation, giving the alcohol shown as the single major product. The procedures are: Hydroboration oxidation: alkene + BH3, then H2O2, OH Oxymercuration: alkene + Hg(OAc), H20; then NaBH4 CH3 CH3 CH3CH2CHCH=CH2 - CH3CH2CHCHCH OH hydroboration/oxidation CH3 CH3CH2CH=C OH CH3CH2CHCHCH СН3 "CH3 Submit Answer Retry Entire Group 1 more group attempt remaining NGTI TUDI References In each case below select the synthetic...
20. Provide the reagents necessary to complete the following the following transformation. A. 1. BH3 THF2....
20. Provide the reagents necessary to complete the following the following transformation. A. 1. BH3 THF2. H2O2. HO- B. H20, H2SO4 C. OsO4 H202 D. CH3CO3H E. 1. CH3CO3H 2. H, H20 21. Provide the major organic product of the reaction below. 10. 2. (CHS uraw the major organic product generated in the reaction below. Pay particular attention to and stereochemical detail. CH3 CH, KMnO4 (warm, conc.) CH, H 23. Give the structure of the alkene which would yield the...
1. Bromination of an alkene is restricted to a syn addition. In this problem you will...
1. Bromination of an alkene is restricted to a syn addition. In this problem you will design an experiment to validate or provide evidence that alkene bromination undergoes syn addition You will use the following starting alkene a) trans-stilbene b) cis-stilbene A. Draw the mechanisms showing all electron flows (curved arrows) and the cyclic halonium intermediate to predict the stereochemical products of the bromination reaction for (a) trans-stilbene and (b) cis-stilbene formed from syn addition. B. Design the experiment to...
I have a question over Problem 9.36 from David Klein’s Chapter 9 on Addition Reactions of...
I have a question over Problem 9.36 from David Klein’s Chapter 9
on Addition Reactions of Alkenes.
I’ve noted acid-catalyzed hydrations in Chapter 9 don’t seem to
note anything about their properties of syn- or anti- addition
processes.
Why don’t acid-catalyzed hydrations contain descriptions of
whether they’re anti- or syn- additions? I know that the compound
in Problem 9.36 doesn’t contain a hydrogen whose stereochemistry
would matter, but what about the acid-catalyzed hydrations with
hydrogens whose stereochemistry does matter?
9.36...
Question 6 Question 7 Check all of the boxes that apply addition leading shown. the manner...
Question 6 Question 7 Check all of the boxes that apply addition leading shown. the manner of Check all of the boxes that apply to the manner of addition leading to the major product o the major product of the reaction the reaction shown. . BH, THF 1. Hg(OAc), HO H2, NaBH 2, HO, NaOH(aq) Hi CHs The endre proocss is concerted from starting material to final product he entire process is concerted trom starting material to final product This...
Acid Catalyzed Hydration-treatment of alkenes with water in the presence of acid catalyst leads to the...
Acid Catalyzed Hydration-treatment of alkenes with water in the presence of acid catalyst leads to the formation of alcohols. H2SO4/H2O > 150°C Mechanism Major Product Acid catalyzed dehydration goes through a carbocation intermediate. This means that the Markovnikov product is obtained when carbocation rearrangements do not occur. The need for excessively high temperatures makes this reaction of limited use in laboratory synthesis. Oxymercuration - Oxymercuration involves the addition of Hg to the alkene using mercury (II) acetate Hg(OAc) followed by...
In an addition reaction to an alkene, the pi bond plays the role of nucleophile electrophile...
In an addition reaction to an alkene, the pi bond plays the role of nucleophile electrophile leaving group Select the product that results from the anti-Markovnikov/syn addition of H and OH to the following alkene. I II III IV What is the IUPAC name for the molecule shown below? 3-(l-butynyl)pentane 5-ethyl-3-octyne 3-ethyl-4-heptyne 5-ethyl-3-heptyne What would be the major product obtained from the addition of HBr to 2-methylpentene? 1-bromo-2-methylpentane 2-bromo-2-methylpentane 3-bromo-2-methylpentane 1-bromo-2-methylpentene What is the reaction product when 4-methyl-2-pentyne is reacted...
(C) Protonation of alkene to form a carbocation followed by addition of bromide ion (D) Addition...
(C) Protonation of alkene to form a carbocation followed by addition of bromide ion (D) Addition of the proton to one face of the alkene with simultaneous delivery of a bromide ion from a different molecule of H-Br. 11. Which compound is the strongest nmucleophile for reaction of methane methanesulfonate (CHOS0.CH) in methanol at room temperature? (You may assume that everything is soluble in methanol) (A) potassium bromide (B) cesium iodide (C) sodiam chloride (D) lithium flaoride 12. Which proton...
5. [14 pts) Provide the major products of reacting the alkene shown in the middle of...
5. [14 pts) Provide the major products of reacting the alkene shown in the middle of the scheme below with all the reagents independently. Draw the products' structures in the corresponding table below showing whether it is a Syn or Anti addition when applicable. No mechanism required! (3 points cach organic product and 2 points for the stereochemistry. Adding the stereochemistry when it is not needed will be penalized) HO Acidic Medium 1) BH, THE 2) H2O2, KOH с HCI...
15) What synthetic goal is achieved by subjecting an alkene to BH3-THF, followed by oxidative working using H2O2 and NaOH? A) Markovnikov addition of water where relative stereochemistry is preserved B) Markovnikov addition of water where relative stereochemistry is scrambled (or destroyed) C) Anti-Markovnikov addition of water where relative stereochemistry is preserved D) Anti-Markovnikov addition of water where relative stereochemistry is scrambled (or destroyed) 16) Which of the following reaction occur by anti-addition to an alkene? A) Br2 B) BH3-THF,...
REVIEW TOPICS Relerences In each case below select the synthetic procedures that could be used to carry out the transformation, giving the alcohol shown as the single major product. The procedures are: Hydroboration oxidation: alkene + BH3, then H2O2, OH Oxymercuration: alkene + Hg(OAc), H20; then NaBH4 CH3 CH3 CH3CH2CHCH=CH2 - CH3CH2CHCHCH OH hydroboration/oxidation CH3 CH3CH2CH=C OH CH3CH2CHCHCH СН3 "CH3 Submit Answer Retry Entire Group 1 more group attempt remaining NGTI TUDI References In each case below select the synthetic...
20. Provide the reagents necessary to complete the following the following transformation. A. 1. BH3 THF2. H2O2. HO- B. H20, H2SO4 C. OsO4 H202 D. CH3CO3H E. 1. CH3CO3H 2. H, H20 21. Provide the major organic product of the reaction below. 10. 2. (CHS uraw the major organic product generated in the reaction below. Pay particular attention to and stereochemical detail. CH3 CH, KMnO4 (warm, conc.) CH, H 23. Give the structure of the alkene which would yield the...
1. Bromination of an alkene is restricted to a syn addition. In this problem you will design an experiment to validate or provide evidence that alkene bromination undergoes syn addition You will use the following starting alkene a) trans-stilbene b) cis-stilbene A. Draw the mechanisms showing all electron flows (curved arrows) and the cyclic halonium intermediate to predict the stereochemical products of the bromination reaction for (a) trans-stilbene and (b) cis-stilbene formed from syn addition. B. Design the experiment to...
I have a question over Problem 9.36 from David Klein’s Chapter 9
on Addition Reactions of Alkenes.
I’ve noted acid-catalyzed hydrations in Chapter 9 don’t seem to
note anything about their properties of syn- or anti- addition
processes.
Why don’t acid-catalyzed hydrations contain descriptions of
whether they’re anti- or syn- additions? I know that the compound
in Problem 9.36 doesn’t contain a hydrogen whose stereochemistry
would matter, but what about the acid-catalyzed hydrations with
hydrogens whose stereochemistry does matter?
9.36...
Question 6 Question 7 Check all of the boxes that apply addition leading shown. the manner of Check all of the boxes that apply to the manner of addition leading to the major product o the major product of the reaction the reaction shown. . BH, THF 1. Hg(OAc), HO H2, NaBH 2, HO, NaOH(aq) Hi CHs The endre proocss is concerted from starting material to final product he entire process is concerted trom starting material to final product This...
Acid Catalyzed Hydration-treatment of alkenes with water in the presence of acid catalyst leads to the formation of alcohols. H2SO4/H2O > 150°C Mechanism Major Product Acid catalyzed dehydration goes through a carbocation intermediate. This means that the Markovnikov product is obtained when carbocation rearrangements do not occur. The need for excessively high temperatures makes this reaction of limited use in laboratory synthesis. Oxymercuration - Oxymercuration involves the addition of Hg to the alkene using mercury (II) acetate Hg(OAc) followed by...
In an addition reaction to an alkene, the pi bond plays the role of nucleophile electrophile leaving group Select the product that results from the anti-Markovnikov/syn addition of H and OH to the following alkene. I II III IV What is the IUPAC name for the molecule shown below? 3-(l-butynyl)pentane 5-ethyl-3-octyne 3-ethyl-4-heptyne 5-ethyl-3-heptyne What would be the major product obtained from the addition of HBr to 2-methylpentene? 1-bromo-2-methylpentane 2-bromo-2-methylpentane 3-bromo-2-methylpentane 1-bromo-2-methylpentene What is the reaction product when 4-methyl-2-pentyne is reacted...
(C) Protonation of alkene to form a carbocation followed by addition of bromide ion (D) Addition of the proton to one face of the alkene with simultaneous delivery of a bromide ion from a different molecule of H-Br. 11. Which compound is the strongest nmucleophile for reaction of methane methanesulfonate (CHOS0.CH) in methanol at room temperature? (You may assume that everything is soluble in methanol) (A) potassium bromide (B) cesium iodide (C) sodiam chloride (D) lithium flaoride 12. Which proton...
5. [14 pts) Provide the major products of reacting the alkene shown in the middle of the scheme below with all the reagents independently. Draw the products' structures in the corresponding table below showing whether it is a Syn or Anti addition when applicable. No mechanism required! (3 points cach organic product and 2 points for the stereochemistry. Adding the stereochemistry when it is not needed will be penalized) HO Acidic Medium 1) BH, THE 2) H2O2, KOH с HCI...
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