Bromination of an alkene by N-bromosuccinimide (NBS) in the presence of light or peroxide is a...
Bromination of an alkene by N-bromosuccinimide (NBS) in the presence of light or peroxide is a radical reaction and produces an allylic bromide. For the following bromination of 3-methylcyclopentene, select the allylic bromides from the set at the right that would be products of the reaction.
Homework Answers
This problem is based on the concept of allylic bromination.
Allylic bromination of Alkenes can occur on reaction of alkene with N-Bromo-succinimide in presence of light.
The carbon adjacent to the double bond is called as allylic carbon. These carbons undergo allylic halogenations via free radical mechanism.
In the given molecule, there are 2 allylic carbons, hence more than 1 product will be formed.
The reactions with respect to the first radical position are given below:
The reactions with respect to the first radical position are given below:
The possible allylic brominated products are given below:
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Bromination of an alkene by N-bromosuccinimide (NBS) in the presence of light or peroxide is a...
The compound below is treated with N-bromosuccinimide (NBS) in the presence of light. Draw both resonance...
The compound below is treated with N-bromosuccinimide (NBS) in the presence of light. Draw both resonance structures for the radical produced by reaction of the compound with a bromine atom. Assume reaction occurs only at the weakest C-H bond. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms, Review Topics] [References) The compound below is treated with N-bromosuccinimide (NBS) in the presence of light. Draw both resonance structures for the radical...
The compound below is treated with N-bromosuccinimide (NBS) in the presence of light. Draw both resonance...
The compound below is treated with N-bromosuccinimide (NBS) in the presence of light. Draw both resonance structures for the radical produced by reaction of the compound with a bromine atom. Assume reaction occurs only at the weakest C-H bond. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Separate resonance structures using the symbol from the drop-down menu. • Include all valence radical electrons in your answer. 1.) The compound...
The compound below is treated with N-bromosuccinimide (NBS) in the presence of light. Draw both resonance...
The compound below is treated with N-bromosuccinimide (NBS) in the presence of light. Draw both resonance structures for the radical produced by reaction of the compound with a bromine atom. Assume reaction occurs only at the weakest C-H bond. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Separate resonance structures using the symbol from the drop-down menu. • Include all valence radical electrons in your answer.
The compound below is treated with N-bromosuccinimide (NBS) in the presence of light. Draw both resonance...
The compound below is treated with N-bromosuccinimide (NBS) in the presence of light. Draw both resonance structures for the radical produced by reaction of the compound with a bromine atom. Assume reaction occurs only at the weakest C-H bond. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. Separate resonance structures using the symbol from the drop-down menu. • Include all valence radical electrons in your answer.
Explantion: In a radical allylic bromination of alkenes with NBS reaction, why does allylic bromination occur...
Explantion: In a radical allylic bromination of alkenes with NBS reaction, why does allylic bromination occur instead of alkene bromination? Secondly, why does the more substituted alkene predominate if more than one alkene can form from such a reaction?
7 7) Alkenes can be selectively brominated in the allylic positions with NBS in CCl4. The...
7
7) Alkenes can be selectively brominated in the allylic positions with NBS in CCl4. The reaction is selective for substitution at the allylic positions and the allylic bromide product usually is the one with the most substituted and/or stable alkene bond. For example, allylic bromination of 1-hexene produces only trans-1-bromo-2-hexene. (8 points) a. Write the reaction for the light initiated bromination of cyclohexene with NBS in CCIA. b. Write the mechanism using fishhook arrows to show bond making and...
Answer the following questions about radical halogenation QUESTION 1 Performing allylic bromination of an asymmetric alkene...
Answer the following questions about radical halogenation
QUESTION 1 Performing allylic bromination of an asymmetric alkene produces two regiochemical outcomes due to resonance, and two conformations (R) and (S) for each chirality center produced. This is further complicated if you make the mistake of using Br2 as your source of bromine radicals, as the addition reaction producing alkyl dibromides competes with the allylic bromination. Br2, hv ??? Categorize each of the compounds shown below as an [A] allylic bromination product,...
1.1What is the major product formed upon radical bromination of (S)-3-methylhexane? Select the best response. Draw...
1.1What is the major product formed upon radical bromination of (S)-3-methylhexane? Select the best response. Draw the full mechanism. A. (S)-3-bromo-3-methylhexane B. (R)-3-bromo-3-methylhexane C. A mixture of (R) and (S) 3-Bromo-3-methylhexane D. (3R)-1-bromo-3-methylhexane 1.2 What is the major product obtained from the reaction of 2-methyl-2-butene with hydrogen bromide in the presence of peroxides?Select the best response. Draw the mechanism. A. 2,3-dibromo-2-methylbutane B. 2-bromo-3-methylbutane C. 2-bromo-2-methylbutane D. (E)-1-bromo-2-methyl-2-butene 1.3 There are 4 major products formed upon treatment of (E)-3-methyl-2-hexene with HBr...
A chemist requires a large amount of 1-bromo-2-hexene as starting material for a synthesis and decides...
A chemist requires a large amount of 1-bromo-2-hexene as starting material for a synthesis and decides to carry out the following NBS allylic bromination reaction in the presence of UV light. Draw the structures of all of the observed products, NBS CH3CH2CH2CH=CHCH3 CCIA • Do not consider alkene stereochemistry or chirality • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner • Separate multiple products using the sign from the drop-down menu...
The compound below is treated with N-bromosuccinimide (NBS) in the presence of light. Draw both resonance structures for the radical produced by reaction of the compound with a bromine atom. Assume reaction occurs only at the weakest C-H bond. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms, Review Topics] [References) The compound below is treated with N-bromosuccinimide (NBS) in the presence of light. Draw both resonance structures for the radical...
The compound below is treated with N-bromosuccinimide (NBS) in the presence of light. Draw both resonance structures for the radical produced by reaction of the compound with a bromine atom. Assume reaction occurs only at the weakest C-H bond. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Separate resonance structures using the symbol from the drop-down menu. • Include all valence radical electrons in your answer. 1.) The compound...
The compound below is treated with N-bromosuccinimide (NBS) in the presence of light. Draw both resonance structures for the radical produced by reaction of the compound with a bromine atom. Assume reaction occurs only at the weakest C-H bond. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Separate resonance structures using the symbol from the drop-down menu. • Include all valence radical electrons in your answer.
The compound below is treated with N-bromosuccinimide (NBS) in the presence of light. Draw both resonance structures for the radical produced by reaction of the compound with a bromine atom. Assume reaction occurs only at the weakest C-H bond. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. Separate resonance structures using the symbol from the drop-down menu. • Include all valence radical electrons in your answer.
7
7) Alkenes can be selectively brominated in the allylic positions with NBS in CCl4. The reaction is selective for substitution at the allylic positions and the allylic bromide product usually is the one with the most substituted and/or stable alkene bond. For example, allylic bromination of 1-hexene produces only trans-1-bromo-2-hexene. (8 points) a. Write the reaction for the light initiated bromination of cyclohexene with NBS in CCIA. b. Write the mechanism using fishhook arrows to show bond making and...
Answer the following questions about radical halogenation
QUESTION 1 Performing allylic bromination of an asymmetric alkene produces two regiochemical outcomes due to resonance, and two conformations (R) and (S) for each chirality center produced. This is further complicated if you make the mistake of using Br2 as your source of bromine radicals, as the addition reaction producing alkyl dibromides competes with the allylic bromination. Br2, hv ??? Categorize each of the compounds shown below as an [A] allylic bromination product,...
A chemist requires a large amount of 1-bromo-2-hexene as starting material for a synthesis and decides to carry out the following NBS allylic bromination reaction in the presence of UV light. Draw the structures of all of the observed products, NBS CH3CH2CH2CH=CHCH3 CCIA • Do not consider alkene stereochemistry or chirality • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner • Separate multiple products using the sign from the drop-down menu...
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