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Organic Chemistry: A Guided Inquiry

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter14: Elimination

Section: Chapter Questions

Problem 33E

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Draw the major product or the starting material of the following reactions. Where
appropriate indicate if the product resulted from SN2, SN1, E2, or E1 in the box provided. When
a racemic mixture is formed, you must draw both enantiomers and write "racemic" in the box.
A)
NaCl
DMSO
B)
C)
Br
H₂O
NaOH
H₂O
E2
D)
NaOH
E)
F)
Cl
CH3OH
H₂O
E2
t-BuOK
E2

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The two pentene isomers react with mCPBA, followed by an aqueous workup with NaOH/H2Ó. Draw the key reaction intermediates and the product(s); use arrow pushing to explain the stereochemical outcomes of the reactions Intermediate Final Products MCPBA CO2OH mCPBA NaOH/H2O CI Intermediate Final Products MCPBA NaOH/H2O 6.
For each section, circle the mechanism from the two options given (SN1 or SN2) and draw the main organic product resulting from that mechanism. Indicate the stereochemistry and if two configurational isomers form, draw both.
Draw all possible products for the following reactions, including stereochemistry. If more than one product can be produced, indicate which would be the major product. а) c) NaOH (CH,CH,),CBr CH3 H3C, CH2CH3 CH,OH, A CH3OK CH3OH H3C CH2CH3 CI b) d) Br Br NaOEt CH30K CH3OH
For each section, circle the mechanism from the two options given (E1 or E2) and draw the main organic product resulting from that mechanism. Indicate the stereochemistry and if two configurational isomers form, draw both.
draw the major product and state whether the relative stereochemistry of the added groups will be anti, syn or unknown
Draw the products of each SN! reaction and indicate the stereochemistry when necessary.
Draw the products for the following chemical reactions, indicating stereochemistry wherever applicable. Indicate if the reaction proceeds via SN1 or SN2 mechanism
When treated with NaOH, the bromide below gives an alkene by the E2 mechanism, by eliminationof the circled atoms: (a) Draw the Newman projection from which elimination takes place. (b) Draw the mechanism. (c) Draw the product with the proper stereochemistry. (d) Assign the proper stereochemical descriptor to the product. (Z, E? Trans,CiS?) (e)What would happen to the stereochemistry of the product if the enantiomer of the starting material were used inthe reaction?
Draw the products of these reactions clearly showing stereochemistry in each case if necessary. If the product is formed as a racemic mixture, clearly draw one stereoisomer with dash/wedge bonds and write “+en”. Circle whether each reaction occurs by an SN1 or SN2 pathway.
Consider the E2 elimination of Compound A, and answer the following questions: (a) Label each stereocenter in Compound A with the correct R or S configuration. (b) Draw the structures of the major product with correct stereochemistry. Assume D and H have the same reactivity.
Draw the structure of the major product. If the answer for the product is a mixture of enantiomers draw one of the enantiomers and write "+ enantiomer." If the answer is a mixture of diaseteromers, draw all of them. Show arrow pushing mechanism and provide reasoning for each.
2. Predict the stereochemical outcome of the following reactions (exo/endo). Indicate the path of reaction by the reactant to explain why you chose that specific stereoisomer. a) NaBH4 LIAIH4 b) d) mCPBA H₂, Pd/C

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