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Chem 30B Fall 2003
MIDTERM #1 ANSWER KEY
Monday October 20th
*DO NOT OPEN THIS EXAM UNTIL INSTRUCTED TO DO SO*
Week 7 Ethers, Epoxides, and Thiols Continued
1. Predict the reagents for the following transformations.
2. The following drugs can be synthesized from either ethylene oxide or epichlorohydrin. Find the
building blocks in the following molecules and propo
ORGANIC CHEMISTRY 30B
MIDTERM EXAM I
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TA (circle name):
Week 5 Recitation Handout: Alcohols
1. Predict the product for the following reactions.
2. Discuss the leaving group abilities for the following: OH-, H2O, CH3SO3-, CH3PhSO3-.
3. 3-Methyl-2-butanol is heated in acid and two isomeric alkenes are formed. Pr
1. Show how 1,2-dimethoxyethane and water interact through hydrogen bonding. Is water a hydrogen
bond donor, acceptor, or both? How about 1,3-dimethoxyethane?
2. Fill in the missing reactants, reagents, or product(s) for the following reactions:
1) Propose a synthe/c route (a series of reac/ons) to achieve each of the following transforma/ons:
1) Propose a synthe/c route (a series of reac/ons) to achieve each of the following transf
1) Draw the structures of the following compounds:
Week 8 Recitation: Organometallic and Carbonyl Chemistry
1. Draw the structures of the following compounds:
2. Using the generic ketone below, where R and R are either saturated alkyl groups or hydrogen,
explain with resonance structures why ketones and a
Week 9 Recitation Handout: Enols and Carboxylic Acid Chemistry
1) Show the mechanism of how (R)-3-phenyl-2-butanone is racemized under either acidic or basic
2) Fill in the reagents and products of the following:
3) Fill in the reagents and th
TD Handout 8
1. Provide Reagents for the following reactions to prepare compound 10.
2. Propose a forward synthesis for preparing compound 10 starting from the starting material given
below. (hint: this should occur reasonably in four steps)
3. Draw the m
1) Fill in the blanks:
2) Propose a synthe6c pathway. Bonus: use 1-butene as your only carbon source.
3) Predict the product(s):
4) What reagents/steps you would need to achieve the following transforma6on?
5) Draw t
1) Fill in the blanks
2) Fill in the blanks
3) Propose a synthe7c route to achieve the following transforma7on
4) Predict the product. Draw the mechanisms and use them to jus7fy your answer.
Week 10 Worksheet Carboxylic Acid Derivatives
1. For each of the following compounds label the functional groups. The possible choices are the
2. Draw the structures of the following compounds:
3. Rank the following in terms of reactivity towar