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Chemistry LibreTexts

Quiz 2

1. Give the best answer for the following multiple choice and labeling questions.


a) Which of the following will not react with a grignard reagent?

A) butyraldehyde

B) butan-2-one

C) 2-butanol

D) 1-butene

E) 1-butyne


b) The addition of a grignard reagent to a carbonyl is based on collision of a nucleophile to fill what acceptor orbital?

A) a s bonding orbital

B) a s* antibonding orbital

C) an empty p orbital

D) a p  bonding orbital

E) a p* antibonding orbital


c) Which reactions will not give a product as a racemic mixture?

A) the addition of phenyl grignard to propionaldehyde

B) epoxidation of an allylic alcohol with a Ti(OiPr)4, tBuOOH, and (–)-diethyl tartrate

C) the addition of NaOCH3 to cyclohexene oxide

D) the acid-catalyzed addition of methanol to cyclohexene oxide

E) an SN1 reaction


d) Which of the following is not a true statement:

A) a silyl ether bond can be cleaved by a fluoride source, such as TBAF

B) LiAlH4 is an oxidizing agent

C) epoxide formation using mCPBA with an alkene proceeds via a concerted mechanism

D) H2CrO4 will oxidize a secondary alcohol to a ketone

E) arene oxides can react with DNA and initiate cancer-causing pathways



e) In the boxes provided, indicate whether each of the following reactive carbon atoms is considered to be electrophilic (E) or nucleophilic (N).  R is used to indicate either H or alkyl.



2. Draw the resonance contributor for a ketone, showing any curved arrows for its formation. Briefly explain what this resonance indicates about the reactivity of a carbonyl.


3. Ethylene oxide is the starting material for the synthesis of “Cellosolve”, an important industrial solvent.  Provide a curved arrow mechanism for this reaction.



4. Provide a curved arrow mechanism for the following transformation.



5. Synthesis 

a) Show how to synthesize the following alcohol where all carbons in the molecule must come from compounds with 3 or fewer carbon atoms.  Include all necessary reagents for the synthesis you propose.





b) Explain why you would need to use a protecting group strategy in a synthesis and give an example of a synthesis that requires the use of a protecting group.  Your synthesis must have at least 3 steps to receive full credit.


6. An aziridinium ion follows a similar reactivity pattern to an epoxide.  The following aziridinium ion reacts with NaOCH3 to form compounds A and B.  Given what you know about the reactivity patterns of epoxides and the information given below, identify the structures of both compounds A and B (in boxes provided).