What is the reaction product of cyclohexene with MCBPA (m-chloroperbenzoic acid)?

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Epoxidation reactions are stereospecific; a trans double bond will give the trans epoxide; cis double bonds will give the cis epoxide.

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The following reaction is an example of a/an ________________   reaction.

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What is the product of this reaction?

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If you have an a,b unsaturated ketone, which reagent, below will reduce only the ketone and leave the double bond alone?

H₂/Pd on C

NaBH₄/CH₃OH

NaBH₄/CH₃OH will only reduce the carbonyl and will leave the double bond alone.

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If you have an a,b unsaturated ketone, which reagent, below will reduce only the double bond and leave the ketone alone?

H₂/Pd on C (1 equivalent)

NaBH₄/CH₃OH

H₂/Pd on C (1 equivalent) will reduce the double bond first.

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If you want to make a saturated alcohol from an a,b unsaturated ketone, what reagent would you need?

H₂/Pd on C (1 equivalent)

H₂/Pd on C (excess)

NaBH₄/CH₃OH

H₂/Pd on C (excess) will reduce the double bond first, and if you have enough, will reduce the ketone to an alcohol. 

NaBH₄/CH₃OH will not reduce the double bond no matter how much you have. H^- is a nucleophile and won't attack the double bond because it has high electron density.

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What is the product?

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Amides may be synthesized from carboxylic acids provided that you include a "dehydrating agent" such as DCC (dicyclohexylcarbodiimide).

LiAlH₄ is a strong reducing agent. What are possible starting materials that would be suitable for the following reaction?

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There are quite a few suitable starting materials since LAH is such a strong reducing agent. Benzaldehye as well as the following compounds would work.

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LiAlH₄-type reducing agents have been modified to reduce the strength of this reagent. DIBAL-H is one example. What is the product of the following reduction reaction?

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Common, strong oxidizing agents such as K₂Cr₂O₇ (potassium chromate) will take alcohols to acids. What is the starting material needed for the following reaction?

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What is the starting material?

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Acids + amines + DCC --> amides

What is the thermodynamically most stable enol form of this ketone?

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           Thermodynamic enol              kinetic enol

The more substituted double bond is the most stable. The kinetic enol is formed first, and at low temperatures. 

Name this ester

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four carbon acid - butyric acid or butanoic acid

four carbon alcohol - butanol (butyl alcohol)

butyl butyrate (common) or butyl butanoate (IUPAC)

Name this ester

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What is the product?

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The product is a mixed anhydride.

What is the product?

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The kinetic enolate (less substituted double bond) is formed under these reaction conditions, so alkylation takes place on the least substituted carbon.

What is the product?

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Formation of the thermodynamic enolate occurs under these reaction conditions (room temp, polar protic solvent). 

Will the following reaction occur?

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Yes - esters can be hydrolyzed under basic or acidic conditions.

What functional group is present in this molecule?

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Which of the following cannot be used to synthesize an ester?

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Amides may not be used to sythesize esters; all others (acids, acid chlorides, anhydrides) may. 

Name this compound:

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What is the product?

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What is the product?

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What is the reagent needed for the following reaction?

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Note: formic acid is HCO₂H

What are the starting materials needed to make this compound?

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Name this compound:

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What are the products?

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How many alpha protons are in this molecule?

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Four - three to the right of the carbonyl carbon and one to the left.

What would the NMR spectrum of this ketone look like?

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They would both have a carbonyl stretch around 1700

cm^-1, but the carboxylic acid would also have a large, broad OH stretch around 3500 cm^-1.

What is the product of the following reaction?

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What is the starting material?

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Anhydrides may be prepared by heating the heck out of acids if the acids are in close proximity.

Which compound has the more acidic protons?

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Compound B (1,3-diketone) has the most acidic protons because the enolate is stabilized by several resonance forms.

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Which carboxylic acid derivative has the highest reactivity?

Amide

Ester

Carboxylic acid

Acid Chloride

Anhydride

The order of reactivity is:

Acid Chlorides > Anhydrides > Esters, acids > Amides

Name this compound:

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This is an acid chloride so the suffix is "oyl chloride". It is a derivative of benzoic acid, so you drop  the "ic acid" and replace it with the appropriate suffix.

Benzoyl chloride

Which of the following compounds is more reactive towards nucleophilic attack?

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What is the reagent needed to make an acid chloride from a carboxylic acid?

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What reagents are needed to make the following compound from benzene?

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Friedel-Crafts acylation reactions require an acid chloride and AlCl₃ catalyst.

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What are the reagents needed for the following reaction?

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This is a Friedel-Crafts alkylation and requires a haloalkane and aluminum chloride catalyst. This reaction works best if the carbocation that would result from the alkyl halide cannot rearrange - a simple alkyl halide like that above, or a tertiary alkyl halide. 

What are the products of the following reaction?

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Nitration of an aromatic ring is an electrophilic aromatic substitution reaction. Chloro and methy substituents are both ortho,para-directors, so the nitro group goes ortho and para to both groups. The isomer with the nitro group between the groups (ortho to both) will not form because of steric hindrance in a 1,2,3-trisubstituted benzene. 

Is this compound aromatic?

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Yes, it is planar, cyclic, fully conjugated and satisfies Huckel's rule (4n + 2 electrons, where n = 0).

Is pyrolle aromatic?

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Explain why pyridine is a good base, but pyrolle is not.

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pyridine   pyrolle   

Both compounds are aromatic, but the lone pair on nitrogen has a different role in each. In pyridine, the lone pair is orthogonal to the aromatic system and doesn't participate in the pi system. It is available for bonding. In pyrolle, the lone pair is part of the aromatic system. If it were to bond to a proton, that would disrupt the aromatic system.

Label the following compounds as aromatic, antiaromatic or non-aromatic.

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Which of the following compounds will react fastest in electrophilic aromatic substitution reactions?

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What are the four criteria that must be met for a compound to be considered aromatic?

1) planar

2) fully conjugated

3) cyclic

4) 4n+2 electrons (Huckel's Rule)

What is the product?

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intramolecular Friedel Crafts acylation reaction

Explain the following reaction:

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Friedel-Crafts reactions go through a carbocation-like intermediate which will rearrange to give the most stable carbocations.

Stability:  Primary < secondary < tertiary

Which of the following compounds are meta directors in electrophilic aromatic substitution reactions?

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All meta directors are deactivating. They are substituents that have a partially positive atom bonded to the aromatic ring. All substituents with a carbonyl group (aldehydes, ketones, carboxylic acids), -NO₂, -SO₃H, -CN, are meta directors.

Which is faster?

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What is the product of this reaction?

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A Grignard reagent will add twice to an acid chloride or an ester. The first step is a substutiton reaction that gives a ketone as a product; the next step is the reaction of that ketone with another Grignard reagent to give an addition product.

What is the product?

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Grignard reagents and organolithium reagents will add 1,2 to an a,b-unsaturated carbonyl (they add to the ketone). 

What is the product?

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An organocopper reagent will add 1,4 to an a,b-unsaturated carbonyl compound.

What is the reagent?

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 This is an addition reaction - a new carbon-carbon bond is formed at the carbonyl, turning it into an alcohol and a new 2-carbon fragment is added. Grignard or organolithium reagents will do this, so the reagent can be either CH₃CH₂MgBr or CH₃CH₂Li

What is the product?

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LiAlH₄ (LAH) is a very strong reducing agent and will take ketones to alcohols, aldehydes to alcohols and amides to amines.

What is the product?

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NaBH4 (sodium borohydride) is a mild reducing agent and will reduce ketones and aldehydes to alcohols but not esters or acid chlorides.