Exam 1 Review
Exam 2 Review
Aldehydes/Ketones
Carb. Acids
Nomenclature
100
Rank the following from most to least acidic:
1 2 3
3 > 2 > 1
100
Which of the following compounds has a conjugated by system (if any) and explain why.
The middle compound, the pi bonds are only separated by a single bond.
100
What functional group is formed when a primary amine reacts with an aldehyde/ketone?
Imine 
100
Rank the following compounds in order of increasing acidity:
1 2 3
(least acidic) 2 < 1 < 3 (most acidic)
100
How do you list a ketone and an alcohol as a substituent on a carbon chain?
Ketone: "oxo"
Alcohol: "hydroxy"
200
What reagents are necessary for this transformation?
1) NaOH
2) PCC
200
Are halogens activating or deactivating groups? Where do they direct (ortho/para or meta)?
Deactivating, ortho/para.
200
What two compounds are needed to form an enamine under acidic conditions?
An aldehyde/ketone and a secondary amine
200
What must be present on the starting material if when reacted with Jone's (Na2Cr2O7) a carboxylic acid is formed?
Primary alcohol
200
Name the following compound:
(S)-4-methylhexan-3-one
300
Reagent?
1) EtMgBr
2)H2O
300
Is this compound aromatic, nonaromatic or anti-aromatic? Explain.
Aromatic: cyclic/conjugated, flat, 6 pi electrons.
300
What reagent is needed to form an aldehyde from a terminal alkyne?
300
What reagent is used to convert an acid halide into a anhydride?
1. COOH
2. Pryidine
300
What is the priority order when listing functional groups on a compound?
aldehydes > ketones > alcohols > multiple bonds > halogens/alkyl groups
400
What is the major pathway (Sn1, Sn2, E1 or E2) when reacting an alcohol with NaH and a 2o RX?
E2
400
Which of the following compounds is the most activated towards EAS reactions? The least activated?
Bottom left is most activated, it contains two strong activating groups. Top right is most deactivated, it ONLY contains a deactivating group.
400
When using acetal formation in synthesis as a protecting group, which reagent do you need to use to convert the acetal back into the aldehyde/ketone?
H2O, H+
400
What is the only compound that a Gilman reagent will react with?
Acid Halide
400
Name the following compound:
(R)-4-chloro-2-oxopentanal
500
What are the two reagents used to form an epoxide on an alkene?
MCPBA and Br2,H2O/NaOH
500
Identify the number of pi electrons in the following compound:
6 Pi electrons
500
In Wittig reactions, which isomer (E or Z) is favored when the ylide contains electron withdrawing groups?
E Isomer
500
How many alcohols are formed when a cyclic ester is reduced using LAH?
2 OH's
500
Name the following compound:
(R)-2-hydroxy-4-methylhexe-3-enal