Homework Answers
In Sn2 reactions, both addition and elimination takes place in a single step. The addition of OH- take place from the back side or opposite side from where the Br leaves and therefore inverted product is formed.
Ans: (S)-2-butanol
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PROBLEM 11-2 What product would you expect to obtain from Sn2 reaction of OH with (R)-2-...
If you did an SN2 reaction with R-2-bromobutane what would the stereochemistry of the product be?...
If you did an SN2 reaction with R-2-bromobutane what would the stereochemistry of the product be? a) R b) S c) achiral d) racemic mixture e) NA If you did an SN1 reaction with S-3-bromohexane what would the stereochemistry of the product be a) R b) S c) achiral d) racemic mixture e) NA
2. What product would you expect from the following reaction? 2. What product would you expect...
2. What product would you expect from the following
reaction?
2. What product would you expect from the following reaction? ÇOCH H+ CO CHE A. in ÇOCH3 B CO.CH ÇO,CHE D. CO,CHE E
QUESTION 4 What product(s) would you expect to obtain from the following S N2 reaction? CH3ON...
QUESTION 4 What product(s) would you expect to obtain from the following S N2 reaction? CH3ON CH3OH Осн, сH,0 I व CH3 CH3CH2H 11 An equimolar mixture of I and II. III None of these O
11.32 ▲ Which reaction in each of the following pairs would you expect to be faster?...
11.32 ▲ Which reaction in each of the following pairs would you expect to be faster? (a) The SN2 displacement by I- on CH3Cl or on CH3OTos (b) The SN2 displacement by CH3CO2 on bromoethane or or bromocyclohexane (c) The SN2 displacement on 2-bromopropane by CH3CH20- or by CN (d) The SN2 displacement by HC C- on bromomethane in benzene or in acetonitrile 11.33 Predict the product and give the stereochemistry resulting from reaction of each of the following nucleophiles...
Draw the structure of the compound you would expect from SN2 reaction of the molecule below...
Draw the structure of the compound you would expect from SN2
reaction of the molecule below with NaCN.
Use the wedge/hash bond tools to indicate stereochemistry.
Include H atoms at chiral centers only.
If a group is achiral, do not use wedged or hashed bonds on
it.
You may use the OWL references to look up acidities if you want
to compare leaving groups.
If the following reaction would undergo SN2, what would be the structure(s) of the product(s)? OH...
If the following reaction would undergo SN2, what would be the structure(s) of the product(s)? OH Me Me O OD < 00
t-Bu What product(s) would you expect to obtain from acid-catalyzed hydrolysis of the single epoxide stereoisomer...
t-Bu What product(s) would you expect to obtain from acid-catalyzed hydrolysis of the single epoxide stereoisomer above? - Use the wedge/hash bond tools to indicate stereochemistry where it exists. Keep the alkyl group in the same orientation as in the figure. . If the reaction produces a racemie mixture, draw both stereoisomers. 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...
Give the structure of the products you would expect from the reaction (if any) of 2-butyne...
Give the structure of the products you would expect from the reaction (if any) of 2-butyne with Li/liquid NH3. If there is no product, simply draw the reactant, 2-butyne Give the structure of the products you would expect from the reaction (if any) of 2-butyne with O3, then HOAc. If there is no product, simply draw the reactant, 2-butyne. How many equivalents of product will be created for one equivalent reactant?
Draw the SN2 mechanism of the reaction between (S)-2-bromobutane and iodid ion. Show lone pairs, electron...
Draw the SN2 mechanism of the reaction between (S)-2-bromobutane
and iodid ion. Show lone pairs, electron pushing arrows, 3-D view
to reflect appropriate stereochemistry, reactants, transition
states, and products. name the product. draw and completely label a
reaction energy diagram corresponding to the mechanism you have
drawn.
f. Draw the Sn2 mechanism of the reaction between (s)-2-bromobutane and iodide ion. Show lone pairs, electron pushing arrows, 3-D view to reflect appropriate stereochemistry, reactants, transition states, and products. Name the product....
The next several questions will refer to the SN2 mechanism. (21 pts) Add arrows and structures...
The next several questions will refer to the SN2 mechanism. (21 pts) Add arrows and structures to the reaction mechanism below (10 pts) 2. а. Br OH HSO4 b. In the reaction above, what is the purpose of sulfuric acid? (2 pts) If you were to monitor your reaction progress using silica TLC, would you expect 1-butanol or 1-bromobutane to move higher up the TLC plate? Justify your answer by describing the interactions with silica (5 pts) c. d. Would...
If you did an SN2 reaction with R-2-bromobutane what would the stereochemistry of the product be? a) R b) S c) achiral d) racemic mixture e) NA If you did an SN1 reaction with S-3-bromohexane what would the stereochemistry of the product be a) R b) S c) achiral d) racemic mixture e) NA
2. What product would you expect from the following
reaction?
2. What product would you expect from the following reaction? ÇOCH H+ CO CHE A. in ÇOCH3 B CO.CH ÇO,CHE D. CO,CHE E
QUESTION 4 What product(s) would you expect to obtain from the following S N2 reaction? CH3ON CH3OH Осн, сH,0 I व CH3 CH3CH2H 11 An equimolar mixture of I and II. III None of these O
11.32 ▲ Which reaction in each of the following pairs would you expect to be faster? (a) The SN2 displacement by I- on CH3Cl or on CH3OTos (b) The SN2 displacement by CH3CO2 on bromoethane or or bromocyclohexane (c) The SN2 displacement on 2-bromopropane by CH3CH20- or by CN (d) The SN2 displacement by HC C- on bromomethane in benzene or in acetonitrile 11.33 Predict the product and give the stereochemistry resulting from reaction of each of the following nucleophiles...
Draw the structure of the compound you would expect from SN2
reaction of the molecule below with NaCN.
Use the wedge/hash bond tools to indicate stereochemistry.
Include H atoms at chiral centers only.
If a group is achiral, do not use wedged or hashed bonds on
it.
You may use the OWL references to look up acidities if you want
to compare leaving groups.
If the following reaction would undergo SN2, what would be the structure(s) of the product(s)? OH Me Me O OD < 00
t-Bu What product(s) would you expect to obtain from acid-catalyzed hydrolysis of the single epoxide stereoisomer above? - Use the wedge/hash bond tools to indicate stereochemistry where it exists. Keep the alkyl group in the same orientation as in the figure. . If the reaction produces a racemie mixture, draw both stereoisomers. 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...
Draw the SN2 mechanism of the reaction between (S)-2-bromobutane
and iodid ion. Show lone pairs, electron pushing arrows, 3-D view
to reflect appropriate stereochemistry, reactants, transition
states, and products. name the product. draw and completely label a
reaction energy diagram corresponding to the mechanism you have
drawn.
f. Draw the Sn2 mechanism of the reaction between (s)-2-bromobutane and iodide ion. Show lone pairs, electron pushing arrows, 3-D view to reflect appropriate stereochemistry, reactants, transition states, and products. Name the product....
The next several questions will refer to the SN2 mechanism. (21 pts) Add arrows and structures to the reaction mechanism below (10 pts) 2. а. Br OH HSO4 b. In the reaction above, what is the purpose of sulfuric acid? (2 pts) If you were to monitor your reaction progress using silica TLC, would you expect 1-butanol or 1-bromobutane to move higher up the TLC plate? Justify your answer by describing the interactions with silica (5 pts) c. d. Would...
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