Signature h o ho cat amount assume no dehydration on

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Signature_________________________ H O HO cat. amount (assume no dehydration on this step) H 3 O heat O O 0.5 equivalents CH 3 CH 2 O H 3 O (assume no ester cleavage) 1) 2) mild
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Pg 9 _____________(23) 17. (3 or 5 pts each) Fill in the box with the product or products that are missing from the following chemical reaction equations. When a racemic mixture is formed, you must write "racemic" under both structures EVEN THOUGH YOU DREW BOTH STRUCTURES . If an E,Z mixture is formed as your product in any step you must draw both the E and Z products. Signature_________________________ O HO cat. amount (assume no dehydration on this step) H 3 O heat O H H 18. (17 pts) Using any reagents turn the starting material into the indicated product. All carbon atoms must come from the starting material. Draw all molecules synthesized along the way. When it doubt, draw the molecule! Hint: this should look familiar as a homework problem. All the carbon atoms of the product must come from the starting material OH ? OH
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Pg 10 _____________(17) Signature_________________________ All the carbon atoms of the product must come from the starting material ? 18 (cont.) Using any reagents turn the starting material into the indicated product. All carbon atoms must come from the starting material. Draw all molecules synthesized along the way. When it doubt, draw the molecule! OH O O O O O O racemic ? H O (10 pts) All the carbon atoms of the product must come from the starting material (7 pts)
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All the carbon atoms of the product must come from the starting material ? 18 (cont.) Using any reagents turn the starting material into the indicated product. All carbon atoms must come from the starting material. Draw all molecules synthesized along the way. When it doubt, draw the molecule! Pg 11 _____________(19) Signature_________________________ (19 pts) OH O O I know this is a tough one, but think about it systematically. You should be familiar with all of the chemistry required. It provides a nice example of how organic synthesis can be used to convert a relatively inexpensive and simple starting material such as ethanol into a relatively complex product such as the α , β -unsaturated ketone.
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Pg 12 _____________(15) 19. (15 pts) Save this until the end, it is an "apply what you know" question. Here is what you need to know; in most cases such as the examples below, proton transfer takes place much, much faster than other types of reactions such as nucleophiles reacting with carbonyl groups . Here is what you also do not know yet; LDA is a base that is used a great deal in organic synthesis because it is so sterically hindered by the isopropyl groups that it cannot act as a nucleophile.
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