The main product in the following reaction is: CH,-CH–CH,Br + CH,CH,O" CH, ÇH, (a) CH,-CH-CH,OCH,CH, (b) CH,- OCH,CH, (c) CH, CH-CH,OH CH, (d) CH,-OH CH, CH,

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter20: Acidity And Pka Of Phenols
Section: Chapter Questions
Problem 11E
icon
Related questions
icon
Concept explainers
Question
The high reactivity of alkyl halides can be explained in terms of nature of C-X bond which is highly polarized
covalent bond due to large difference in the electronegativities of carbon and halogen atom. This polarity
is responsible for the nucleophilic substitution reactions of alkyl halides which mostly occur by Swa and Swa
mechanisms. Sy reaction is a two-step process and in the first step, R-X ionizes to give carbocation (slow
process). In the second step, the nucleophile attacks the carbocation from either side to form the product
(fast process). In Swi reaction, there can be racemization and inversion. Swi reaction is favored by heavy
(bulky) groups on the carbon atom attached to halogens. i.e., R,C-X>R;CH-X>R-CH,X>CH,X. In Sna reaction,
the strong nucleophile OH attacks from the opposite side of the chlorine atom to give an intermediate
(transition state) which breaks to yield the product (alcohol) and leaving (X) group. The alcohol has a
configuration opposite to that of the bromide and is said to proceed with inversion of configuration. SN;
reaction is favored by small groups on the carbon atom attached to halogen i.e., CH-X>R-
CH,X>R;CHX>R.C-X.
The main product in the following reaction is:
CH,-CH-CH,Br + CH,CH,O"
CH,
CH,
(0 сH, сн-сн,осн, сн, ф) сн, —осн, сн, (0) СН, — ҫн—сн,он
SH,
(d) CH,-COH
ČH,
ČH,
ČH,
ČH,
O D
O A
O B
Transcribed Image Text:The high reactivity of alkyl halides can be explained in terms of nature of C-X bond which is highly polarized covalent bond due to large difference in the electronegativities of carbon and halogen atom. This polarity is responsible for the nucleophilic substitution reactions of alkyl halides which mostly occur by Swa and Swa mechanisms. Sy reaction is a two-step process and in the first step, R-X ionizes to give carbocation (slow process). In the second step, the nucleophile attacks the carbocation from either side to form the product (fast process). In Swi reaction, there can be racemization and inversion. Swi reaction is favored by heavy (bulky) groups on the carbon atom attached to halogens. i.e., R,C-X>R;CH-X>R-CH,X>CH,X. In Sna reaction, the strong nucleophile OH attacks from the opposite side of the chlorine atom to give an intermediate (transition state) which breaks to yield the product (alcohol) and leaving (X) group. The alcohol has a configuration opposite to that of the bromide and is said to proceed with inversion of configuration. SN; reaction is favored by small groups on the carbon atom attached to halogen i.e., CH-X>R- CH,X>R;CHX>R.C-X. The main product in the following reaction is: CH,-CH-CH,Br + CH,CH,O" CH, CH, (0 сH, сн-сн,осн, сн, ф) сн, —осн, сн, (0) СН, — ҫн—сн,он SH, (d) CH,-COH ČH, ČH, ČH, ČH, O D O A O B
Expert Solution
steps

Step by step

Solved in 2 steps with 1 images

Blurred answer
Knowledge Booster
Introduction to Organic Chemistry
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
  • SEE MORE QUESTIONS
Recommended textbooks for you
Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:
9780618974122
Author:
Andrei Straumanis
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305580350
Author:
William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9781305080485
Author:
John E. McMurry
Publisher:
Cengage Learning