(a) Interpretation: The substitution product (including stereochemistry) formed by the treatment of ( R ) -hexan-2-ol with the given series of reagent is to be drawn. The two routes that produce identical products are to be identified. Concept introduction: An alkoxide salt is required to prepare ether. The alkoxide salts are prepared when alcohols are treated with NaH or NaNH 2 . The stereochemistry of the product is retention of configuration. However, stereochemistry is reversed when product is allowed to react further with strong nucleophile, like I − . It is due to S N 2 path of reaction.
(a) Interpretation: The substitution product (including stereochemistry) formed by the treatment of ( R ) -hexan-2-ol with the given series of reagent is to be drawn. The two routes that produce identical products are to be identified. Concept introduction: An alkoxide salt is required to prepare ether. The alkoxide salts are prepared when alcohols are treated with NaH or NaNH 2 . The stereochemistry of the product is retention of configuration. However, stereochemistry is reversed when product is allowed to react further with strong nucleophile, like I − . It is due to S N 2 path of reaction.
Interpretation: The substitution product (including stereochemistry) formed by the treatment of (R)-hexan-2-ol with the given series of reagent is to be drawn. The two routes that produce identical products are to be identified.
Concept introduction: An alkoxide salt is required to prepare ether. The alkoxide salts are prepared when alcohols are treated with NaH or NaNH2. The stereochemistry of the product is retention of configuration. However, stereochemistry is reversed when product is allowed to react further with strong nucleophile, like I−. It is due to SN2 path of reaction.
Interpretation Introduction
(b)
Interpretation: The substitution product (including stereochemistry) formed by the treatment of (R)-hexan-2-ol with the given series of reagent is to be drawn.
Concept introduction: Alcohols are converted into alkyl tosylates by treatment with p-toluenesulfonylchloride(TsCl) in the presence of pyridine. The overall reaction converts −OH (a poor leaving group) into −OTs (a good leaving group), and stereochemistry of the reaction is retained. However, the further strong nucleophilic attack results the inversion in configuration, through SN2 mechanism.
Interpretation Introduction
(c)
Interpretation: The substitution product (including stereochemistry) formed by the treatment of (R)-hexan-2-ol with the given series of reagent is to be drawn.
Concept introduction: Alkyl bromides are obtained by the reaction of 1°or2° alcohols with phosphorous tribromide (PBr3). The reaction yields HOPBr2 as by-product. The mechanism of the reaction is SN2 that results an inversion of configuration product. However, the further strong nucleophilic attack results the inversion in configuration product through SN2 mechanism.
Draw the organic products formed when cyclopentene is treated withfollowing reagent.
(CH3)3COOH, Ti[OCH(CH3)2]4, (−)-DET
Nitromethane is reacted with ethyl prop-2-enoate with EtO-Na+, EtOH 3 equivalents to give the product X(C16). X then reacts with H2/Raney Ni to give the product Y(C14), which in turn reacts with Na to give Z (C12). Indicate which products X, Y and Z are.
Draw the products formed when p-methylaniline (p-CH3C6H4NH2) is treated with each reagent.
a. HCl
b. CH3COCl
c. (CH3CO)2O
d. excess CH3I
e. (CH3)2C = O
f. CH3COCl, AlCl3
g. CH3CO2H
h. NaNO2, HCl
i. Part (b), then CH3COCl, AlCl
j. CH3CHO, NaBH3CN
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