Orgo! Located in photo. 5.The product in the following reaction is formed as a result of a 1,2-methyl shift fromthe initially formed 2° carbocation. Which intermediate correctly illustrates thatcarbocation rearrangement?H,SO,H,OOHOH2(а)(b)(c)(d)6. When HBr is added to 1-butene (as shown in the following reaction equation) thenewly formed stereocenter must be a racemic mixture of both R & S formsbecause (a) 1-butene forms a 1° carbocation, (b) the intermediate 2° carbocationcan be attacked from either face, (c) the intermediate 2° carbocation rearrangesby 1,2 -hydride shifts before the Br- attacks, (d) the two products are achiral:BrtCH CHCH,(S)-2-bromobutaneHBrCH,Planar carbocationCH CHCH,CH:BetCH:Be:(R)-2-bromobutane7. In the reaction shown below which converts an alkene to an alcohol, what speciesacts as the nucleophile in the reaction with the carbocation intermediate?(a) a sulfuric acid molecule, (b) a hydronium ion (c) a neutral water molecule,(d) the C=C of the alkene.slowR-CH=CH2 + H-OSO3HR-CHCH3H20R-CHCH3R-CHCH3 + H3O:SHCHSHO:H-

The reaction takes place by formation of carbonation followed by migration of methyl group to come…

The product in the following reaction is formed as a result of a 1,2-methyl shift from the initially formed 2° carbocation. Which intermediate correctly illustrates that carbocation rearrangement? 5. H,SO, H,O OH2

The product in the following reaction is formed as a result of a 1,2-methyl shift from the initially formed 2° carbocation. Which intermediate correctly illustrates that carbocation rearrangement? 5. H,SO, H,O OH2

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter14: Elimination

Section: Chapter Questions

Problem 46CTQ

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Question

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Orgo! Located in photo.

5.
The product in the following reaction is formed as a result of a 1,2-methyl shift from
the initially formed 2° carbocation. Which intermediate correctly illustrates that
carbocation rearrangement?
H,SO,
H,O
OH
OH2
(а)
(b)
(c)
(d)
6. When HBr is added to 1-butene (as shown in the following reaction equation) the
newly formed stereocenter must be a racemic mixture of both R & S forms
because (a) 1-butene forms a 1° carbocation, (b) the intermediate 2° carbocation
can be attacked from either face, (c) the intermediate 2° carbocation rearranges
by 1,2 -hydride shifts before the Br- attacks, (d) the two products are achiral
:Brt
CH CH
CH,
(S)-2-bromobutane
HBr
CH,
Planar carbocation
CH CH
CH,CH
:Bet
CH
:Be:
(R)-2-bromobutane
7. In the reaction shown below which converts an alkene to an alcohol, what species
acts as the nucleophile in the reaction with the carbocation intermediate?
(a) a sulfuric acid molecule, (b) a hydronium ion (c) a neutral water molecule,
(d) the C=C of the alkene.
slow
R-CH=CH2 + H-OSO3H
R-CHCH3
H20
R-CHCH3
R-CHCH3 + H3O:
SHCHS
HO:
H-

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