Chapter 22: Q19. (page 894)
Question: What product is formed when acetic acid is treated with each reagent: (a) ; (b) , then heat; (c) + DCC?
Short Answer
Answer
a.
b. 
c.
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Chapter 22: Q19. (page 894)
Question: What product is formed when acetic acid is treated with each reagent: (a) ; (b) , then heat; (c) + DCC?
Answer
a.
b. 
c.
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Draw the product formed when the -unsaturated ketone A is treated with each reagent.

(a) NaBH4, CH3OH
(b) H2 (1 equiv), Pd-C
(c) H2 (excess), Pd-C
(d) [1] CH3Li ; [2]H2O
(e) [1] CH3CH2MgBr ; [2]H2O
(f) [1] ; [2]H2O
Question: Which ester, C or D, is more reactive in nucleophilic acyl substitution? Explain your reasoning.


Oct-1-yne (HCCCH2CH2CH2CH2CH2CH3) reacts rapidly with NaH, forming a gas that bubbles out of the reaction mixture, as one product. Oct-1-yne also reacts rapidly with CH3MgBr , and a different gas is produced. Write balanced equations for both reactions and identify the gases formed.
Draw the products formed (including stereoisomers) when each compound is reduced with NaBH4in CH3OH.
Using protecting groups, show how estrone can be converted to ethynylestradiol, a widely used oral contraceptive.
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