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1. Bromination of an alkene is restricted to a syn addition. In this problem you will...
Look up and draw the mechanism for the addition of Br2 to double bonds. Reference the...
Look up and draw the mechanism for the addition of Br2 to
double bonds. Reference the source from which you acquired the
mechanism.
Give the IUPAC name of the major product in the above-mentioned
reaction.
Draw the major product of obtained in the addition of Br2 to
stilbene.
Is this isomer chiral? What would be the optical rotation if
this sample was placed in a polarimeter?
Would a student obtain the same product if you started with
cis-stilbene instead of...
alswering these questions. 1. If the bromination of trans-stilbene proceeded by syn addition what isomer(s) of...
alswering these questions. 1. If the bromination of trans-stilbene proceeded by syn addition what isomer(s) of stilbene dibromide would be formed? 2. If the bromination of trans-stilbene proceeded by anti addition what isomer(s) of stilbene dibromide would be formed? 3. Which isomer(s) of stilbene dibromide would be formed if the reaction followed Mechanism 4? Mechanism 4: Bromination is a multi-step process. In this mechanism, the pi bond attacks the bromine molecule as in Mechanism 1. Some time after the carbocation...
Stereochemistry of bromine addition 1) To investigate the mechanism for the addition of bromine to an...
Stereochemistry of bromine addition 1) To investigate the mechanism for the addition of bromine to an alkene, we will use the melting point of our brominated products. The three possible outcomes for this lab are to obtain 1)only the syn enantiomers, 2)only the anti enantiomers, or 3)a mixture of diastereomers. Match these possible outcomes to the three possible mechanisms described in the lab manual, bromonium ion, concerted Br2 activation, and carbonation 2) In this experiment we don't crystallize the final...
Caption Emphasis Heading 1 Head 1. Complete the structures of possible stereoisomers of the bromination products...
Caption Emphasis Heading 1 Head 1. Complete the structures of possible stereoisomers of the bromination products from in this experiment. Be sure to show stereochemistry. Name Structure Name Structure Br Br (1R,25)-1,2-dibromo- 1,2-diphenylethane (15,25)-1,2-dibromo- 1,2-diphenylethane Br Br Br Br 15,2R)-1,2-dibromo- 1,2-diphenylethane 1 (1R, 2R)-1,2-dibromo- 1,2-diphenylethane Br Br i. Which of the above 1,2-dibromo-1,2-diphenylethane stereoisomers would be called meso-isomers? ii. Which two of the above four 1,2-dibromo-1,2-diphenylethane stereoisomers would make up a racemic mixture? iii. Which of the possible stereoisomers would...
Below are three possible mechanisms for the bromination of trans-stilbene. All mechanisms are possible on paper....
Below are three possible mechanisms for the bromination of
trans-stilbene. All mechanisms are possible on paper. Study each
mechanism and decide what the stereochemical outcome of each would
be and draw the appropriate product (syn, anti, or a mix of both).
Decide which mechanism is most consistent with your data from the
experiment. This work should all be recorded in your lab
notebook.
.
Mechanism A: Br-Br PhPh Mechanism B: Br-Br Br Ph Ph PhPh Mechanism C C-Br: :Br: :Br...
From the lab hand-out: “In this experiment, you will synthesize stilbene dibromide by reacting the alkene,...
From the lab hand-out: “In this experiment, you will synthesize stilbene dibromide by reacting the alkene, trans-stilbene, with Br2 formed in situ from pyridinium tribromide (Figure 1). This reaction takes place and produces two stereocenters, therefore up to three products can be formed; S,S and R,R enantiomers and/or racemic mixture of R,S and S,R which are meso compounds (by definition a meso compound is a molecule with multiple stereocenters that is superimposable on its mirror image)…” After you complete your...
1. What is the expected product melting point if the bromination of stilbene by PHPB is...
1. What is the expected product melting point if the bromination of stilbene by PHPB is completely stereospecific (anti addition)? 2. How would the melting point be affected if the reaction is not completely stereospecific and the dibromide product contains significant amounts of dl-stilbene dibromide, as well as the expected meso stilbene dibromide? Note the widely differing melting points of the meso and dl isomers. 3. What is the theoretical yield of dibromide product in the bromination reaction? 4. How...
Bromination of trans-Stilbene Introduction can drastically valla very viss The alkene halogenation reaction is a class...
Bromination of trans-Stilbene Introduction can drastically valla very viss The alkene halogenation reaction is a class of reacties in which ha s as clectrophiles 10 attack double bond. Reactivity of halogens can drastically in the fileness of a halogenation react For example, the high reactivity of fluorine e of jodine results in very slow orine pas causes a very vigorous reaction while the low reactivity reactions. Chlorine and bromine showmoderate reactivity and a commonly used in this type of reaction:...
a) Draw a chemical equation for the reaction in this lab, clearly indicate the possible stereochemistry...
a) Draw a chemical equation for the reaction in this lab, clearly indicate the possible stereochemistry (R/S) of all potential products (Newman Projection) from cis and trans addition to the double bond of trans-stilbene. (Hint see Expt. 3) Clearly indicate meso compounds if any. Br Br Ph Br Ph Br Br b) Draw a reaction mechanism for the reaction between bromine and trans-stilbene. Clearly shovw the nucleophilic attack of Br- on both carbons of the cyclic bromenium ion and the...
1. Why do you think alkenes would rather undergo catalytic hydrogenation by syn addition rather than...
1. Why do you think alkenes would rather undergo catalytic hydrogenation by syn addition rather than anti addition? Support your answer with an example. (4 pts) 2. What does the word stereoselectivity mean and how does it apply to the catalytic hydrogenation of alkenes? (2 pts) 3. What is the correlation between the heat of hydrogenation of an alkene and its degree of substitution? (2 pts)
Look up and draw the mechanism for the addition of Br2 to
double bonds. Reference the source from which you acquired the
mechanism.
Give the IUPAC name of the major product in the above-mentioned
reaction.
Draw the major product of obtained in the addition of Br2 to
stilbene.
Is this isomer chiral? What would be the optical rotation if
this sample was placed in a polarimeter?
Would a student obtain the same product if you started with
cis-stilbene instead of...
alswering these questions. 1. If the bromination of trans-stilbene proceeded by syn addition what isomer(s) of stilbene dibromide would be formed? 2. If the bromination of trans-stilbene proceeded by anti addition what isomer(s) of stilbene dibromide would be formed? 3. Which isomer(s) of stilbene dibromide would be formed if the reaction followed Mechanism 4? Mechanism 4: Bromination is a multi-step process. In this mechanism, the pi bond attacks the bromine molecule as in Mechanism 1. Some time after the carbocation...
Caption Emphasis Heading 1 Head 1. Complete the structures of possible stereoisomers of the bromination products from in this experiment. Be sure to show stereochemistry. Name Structure Name Structure Br Br (1R,25)-1,2-dibromo- 1,2-diphenylethane (15,25)-1,2-dibromo- 1,2-diphenylethane Br Br Br Br 15,2R)-1,2-dibromo- 1,2-diphenylethane 1 (1R, 2R)-1,2-dibromo- 1,2-diphenylethane Br Br i. Which of the above 1,2-dibromo-1,2-diphenylethane stereoisomers would be called meso-isomers? ii. Which two of the above four 1,2-dibromo-1,2-diphenylethane stereoisomers would make up a racemic mixture? iii. Which of the possible stereoisomers would...
Below are three possible mechanisms for the bromination of
trans-stilbene. All mechanisms are possible on paper. Study each
mechanism and decide what the stereochemical outcome of each would
be and draw the appropriate product (syn, anti, or a mix of both).
Decide which mechanism is most consistent with your data from the
experiment. This work should all be recorded in your lab
notebook.
.
Mechanism A: Br-Br PhPh Mechanism B: Br-Br Br Ph Ph PhPh Mechanism C C-Br: :Br: :Br...
Bromination of trans-Stilbene Introduction can drastically valla very viss The alkene halogenation reaction is a class of reacties in which ha s as clectrophiles 10 attack double bond. Reactivity of halogens can drastically in the fileness of a halogenation react For example, the high reactivity of fluorine e of jodine results in very slow orine pas causes a very vigorous reaction while the low reactivity reactions. Chlorine and bromine showmoderate reactivity and a commonly used in this type of reaction:...
a) Draw a chemical equation for the reaction in this lab, clearly indicate the possible stereochemistry (R/S) of all potential products (Newman Projection) from cis and trans addition to the double bond of trans-stilbene. (Hint see Expt. 3) Clearly indicate meso compounds if any. Br Br Ph Br Ph Br Br b) Draw a reaction mechanism for the reaction between bromine and trans-stilbene. Clearly shovw the nucleophilic attack of Br- on both carbons of the cyclic bromenium ion and the...
1. Why do you think alkenes would rather undergo catalytic hydrogenation by syn addition rather than anti addition? Support your answer with an example. (4 pts) 2. What does the word stereoselectivity mean and how does it apply to the catalytic hydrogenation of alkenes? (2 pts) 3. What is the correlation between the heat of hydrogenation of an alkene and its degree of substitution? (2 pts)
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