Organic Chemistry 2 Final, Reagents and Reactions

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Overall Reactivity of Carbonyl Groups
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Acyl Chloride > acid anhydride > aldehyde > ketone > ester = carboxylic acid > amide
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aldehyde plus Grignard forms a
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secondary alcohol
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When a carbon is bonded to 2 hydrogen and 2 non-identical groups
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enantiotopic (1 signal)
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When a carbon is bonded to 2 hydrogens in a compound with an asymmetric center
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diastereotopic (2 signals)
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(2C + 2 – #H – #X + #N)/2
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Formula for degree of unsaturations
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rings and double bonds count for how may degrees of unsaturation?
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1 – One
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Triple bonds count for how many degrees of unsaturation
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2 – Two
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What are the steps to determining NMR spectrum
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1) Determine degree of unsaturation 2) Look of rings at 6.5 – 8.0 – Number of sub. = 6 – #aromatic protons 3) Look for aldehydes (sharp singlet past 9) Look for alcohols (broad anywhere) 4) Add up integration and match to formula 5) Start putting the pieces together
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Nucleophiles act by donating a pair of ________________________ or its electron _________________________.
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electrons, density
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Formaldehyde + Grignard
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primary alcohol
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Ketone + Grignard
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tertiary alcohol
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When an organometallic performs ring opening, it attacks the __________________ substituted side.
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less
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What are the three main oxidizing agents
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1) Chromic Acid (H2CrO4) – Na2Cr2O7 / H2SO4 2) PCC / Ch2Cl2 3) NaOCl / Ch3COOH
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Chromic Acid will oxidize a secondary alcohol to a __________________.
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Ketone
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Chromic Acid will oxidize a primary alcohol to an __________________ and then to a ______________________.
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aldehyde, carboxylic acid
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PCC will oxidize a primary alcohol to an _____________________.
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aldehyde
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To oxidize a primary alcohol to an aldehyde, use ___________.
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PCC
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To oxidize a primary alcohol to carboxylic acid, use _________________.
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Chromic Acid
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Terminal alkyne + strong base (NaNH2) = _____________________
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acetylide ion
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Acetylide + aldehyde/ketone + weak acid (pyridine) = __________________
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alcohol with triple bond
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Reaction of cyanide with an aldehyde/ketone = ___________________
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cyanohydrin (alcohol with C triple bond N)
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Acid catalyzed hydrolysis of cyanohydrin produces an _____________________________.
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alpha carboxylic acid
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What are the two main hydrides used in reduction reactions
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Lithium aluminum hydride and sodium borohydride
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Which hydride is used to reduce aldehydes and ketones
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sodium borohydride
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sodium borohydride reduces aldehydes to _________________ and ketones to __________________.
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primary alcohols, secondary alcohols
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What is required following the reaction of an aldehyde or ketone with a hydride?
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acid work-up to protonate and create the alcohol
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Catalytic addition of hydrogen with H2 to a cyanohydrin forms a ________________________.
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primary amine
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What is the best way to make a terminal alkene
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Wittig Reaction
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The Wittig reaction involved the reaction of an aldehyde or ketone with a _______________ _______________.
The Wittig reaction involved the reaction of an aldehyde or ketone with a _______________ _______________.
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phosphonium ylide
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The Wittig reaction replaces the carbon oxygen double bond with a _______________, ________________ double bond.
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carbon carbon
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Addition of water to an aldehyde or ketone, produces a ______________.
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Hydrate
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What is a hydrate and what reagents are need to form it.
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Molecule with two -OH groups bonded to the same carbon. H2O and Acid – acid catalyzed
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Acid Catalyzed reaction of aldehydes and ketones with alcohols forms a ____________________ after one addition and a ________________ after the second addition.
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hemiacetal, acetal
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Using a 1,2-diol as a protecting group forms a ___________ membered ring and the use of 1,3-diol forms a ___________ membered ring.
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five, six
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Reaction of aldehydes and ketones with a primary amine and trace acid produces an ___________________.
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Imine
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In the formation of an imine, the carbon, oxygen double bond is replaced by a __________________, ____________________double bond.
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carbon, nitrogen
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What reagents required for the synthesis of imine?
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1) aldehyde / ketone 2) primary amine (RNH2) 3) trace acid
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An enamine is a ________________ amine with a ______________ bond in the alpha, beta position relative to the nitrogen.
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tertiary, double
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In the formation of an enamine…After reacting an aldehyde or ketone with a secondary amine, ________________ is eliminated forming the tertiary amine.
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water
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Integrated values on an NMR are reported in the _______________ form.
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reduced
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The peak intensity changes/remains constant in a double of doublets.
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remains constant
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What determines the reactivity of organometallics?
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The electronegativity of the metal. The more electronegative, the more reactive
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Why are organolithiums more reactive than organocuprates?
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The Organolithium bond is more polar than the organocuprate bond.
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When determining the number of signals in a compound with cyclohexane, keep in mind that the ring can _____________.
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ring flip
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Which reducing agent is used to reduce carboxylic acids and esters
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Lithium aluminum hydride
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What determines the ease in preparation of ylides?
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sterics and degree of substitution.
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When an ylide reacts with an aldehyde or ketone, the P-C bond is ________________ and a ______________ double bond forms between the ______________ carbon and the carbon from the ylide.
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broken, new, carbonyl
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How do you determine if hydrogens are homotopic. enantiotopic. or diastereotopic?
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Deuterium substitution
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Propanoic Acid
Propanoic Acid
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Propanoyl Chloride
Propanoyl Chloride
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Phenyl Propanoate
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Steps for naming esters
Steps for naming esters
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1) R group attached to carboxylic oxygen named first 2) followed by name of acid with “ic acid” replaced by “ate” ethyl ethanoate
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___________________ agents convert alcohols to carbonyls
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oxidizing
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PCC oxidizes primary alcohols to ___________________ and secondary alcohols to ________________?
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aldehydes, ketones
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Chromic acid oxidizes secondary alcohols to _______________ and primary alcohols to ____________________?
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ketones, carboxylic acids
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Wittig reactions form terminal __________________.
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alkenes
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Retrosynthetic analysis of Wittig reagents favor the ________________ substituted alkyl halide.
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less
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When a Grignard reacts with CO2, __________________ is produced.
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a carboxylic acid
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Strong base add _____________________ without the aid of an ___________________ catalyst.
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irreversibly, acid
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What are the strong bases
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1) Grignards 2) Organolithium 3) Hydrides 4) Wittig
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When strong bases add to carbonyl carbons, they add 1,___ and acid is added in a ________________ step.
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2, separate
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Weaker bases require the assistance of an acid _______________.
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catalyst
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Reactivity within aldehydes and ketones is reliant on….
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Substituents. (Both hydrogen is most reactive, 2 large bulky substituents are least reactive)
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If a carbonyl is in the presence of acid, the oxygen acts as a ________________ base and is more _______________.
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Lewis, electrophilic
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The addition of an acid catalyst increases the ________________ of the reaction only.
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rate
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Why is hydrate formation reversible?
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Water and alcohols are weaker nucleophiles
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What conditions are required for hydrate formation and why?
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acidic to increase the electrophilicity of the carbonyl carbon
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Protecting groups, protect ___________________ carbons from reactions that they otherwise would not survive.
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carbonyl
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Grignards in the presence of an _______________ proton, will quench!
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acidic
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When a nucleophile attacks an sp2 carbon, ______________ products can form.
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multiple/2
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Hydrate Mechanism
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Conjugate addition is known as the _____________ product.
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thermodynamic
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Direct addition is known as the _____________ product.
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kinetic
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Enamines are similar to ___________, except that the carbonyl oxygen is replaced with NR2.
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enolates
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The formation of enamines is _________________ catalyzed.
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acid
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Enamine Mechanism
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Why is water/acid added stepwise with grignards?
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Quench
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What reagents make up pyridine chlorochromate
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What conditions are necessary when using PCC and why
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anhydrous to prevent further oxidation
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Bleach oxidation turns secondary alcohols to ___________________ and primary alcohols to ___________________.
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ketones, aldehydes
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In the reduction reaction with hydrides, the nucleophile is the _________________.
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hydride ion (H)
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In a phosphonium ylide, the majority of electron density resides on which atom?
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carbon
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Wittig reactions are preferred for making ___________________ alkenes.
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terminal
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Alpha hydrogens are more acidic because the conjugate ________________ is more stable through _____________.
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base, resonance
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Aldehydes an ketones are more acidic because in an ester, two pairs of protons __________________ for delocalization.
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compete
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LDA will convert ________________ of a carbonyl compound to enolate ions.
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ALL
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Halogenation of the alpha carbon uses what reagents?
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X2 and acid
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Halogenation can be _________________ catalyzed or _________________ promoted.
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acid, base
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In a base promoted halogenation, the base removes an alpha proton and _______________ alpha protons are replaced by the halogen.
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ALL
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In an acid catalyzed halogenation, ______________ alpha proton is replaced.
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One
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In a base promoted halogenation, the _______________ attacks the electrophilic halogen.
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enolate
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Alpha carbon alkylation requires the removal of an alpha carbon with _______________.
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LDA
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____________________is the required solvent for LDA.
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THF
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The kinetic alkylation product is formed _________________ and uses LDA at -78.
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faster
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The thermodynamic alkylation product can be formed using 0.95% _________________ and 0.05% __________________.
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LDA, NaOH
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In an aldol addition, the alpha carbon of one aldehyde/ketone acts as the ________________, and attacks the ________________ carbon of another.
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nucleophile, carbonyl
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The first step of an aldol addition is the removal of an alpha proton with a ________________.
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base
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An alcohol in the 3 position indicates a _________________ addition.
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aldol
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Dehydration of aldol addition forms _____________________________- aldehydes and ketones
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alpha, beta unsaturated
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Aldol condensation requires
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heat and acid, or base and heat
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The basic mechanism for aldol condensation begins with the base removing an alpha proton.
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In a crossed aldol, one of the reactants must have no _________________ protons.
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alpha
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Aside from using one reactant without alpha protons, you can use _____________ and add the other slowly.
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LDA
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To determine the starting material of an aldol addition, locate the new ___________-____________ bond (formed with the alpha carbon, and draw the two reactants.
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carbon carbon
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To determine the starting material of an aldol condensation, convert the _____________-______________ unsaturated carbonyl to a _________________-hydroycarbonyl.
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alpha, beta, beta
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When two ester molecules undergo condensation, the process is called a ____________ condensation.
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Claisen
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The base used in a Claisen condensation is the same as the _________________________.
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leaving group
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Claisen Condensation versus Aldol addition products.
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Carboxylic acids with a carbonyl group at the 3 position will undergo _________________________ in the presence of acid and heat.
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decarboxylation
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Decarboxylation is easier under ______________ conditions
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acidic
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The malonic ester synthesis combines the _______________ of an alpha carbon and the __________________ of a 3-oxocarboxylic acid.
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alkylation, decarboxylation
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Malonic Ester Mechanism
Malonic Ester Mechanism
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Acetoacetic Ester Synthesis
Acetoacetic Ester Synthesis
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The product of the acetoacetic ester synthesis is a ______________ __________________.
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methyl ketone
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Mechanism for the intramolecular claisen (Dieckman)
Mechanism for the intramolecular claisen (Dieckman)
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Acyl chlorides can react with what to form what?
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1) alcohols to form esters 2) water to form carboxylic acids 3) amines to form amides
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Acyl chloride reaction with amines to form amides require ___________ equivalents of the _______________.
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two, amine The first to attack and the second to deprotonate the intermediate
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Esters can react with what to form what?
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1) water to form carboxylic acids 2) alcohol to form new ester 3) amine to form amide (1 equivalent)
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Reaction of an ester with an amine must be in what environment and why.
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basic to avoid the protonation of the amine.
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Ester hydrolysis is an _______________ catalyzed process which also has protonation of the leaving group.
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acid
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How does an acid catalyst increase the rate of ester hydrolysis?
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Increases formation of intermediate by protonating the carbonyl oxygen and increases the leaving ability of the LG by protonating it.
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In the reaction of an ester with an alcohol, excess ______________ is required.
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alcohol
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Carboxylic acids react with what to form what?
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1) alcohols to form esters
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Amides DO NOT react with…
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halides, alcohols, or water
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Amides will react with water and alcohol under ______________ conditions
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acidic / heat
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An amide will react with acid and heat will form a
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carboxylic acid
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An alkyl halide can react with _______________ to form a nitrile which is then converted to a ______________ ________________.
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cyanide, carboxylic acid
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An acid anhydride reacts with water to form two equivalents of a ____________________ __________________.
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carboxylic acid
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Esters and Acyl chlorides undergo _______________ successive reactions to form _________________ ________________.
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two, tertiary alcohols
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Acyl chlorides undergo __________________ successive reactions with hydrides to form a ___________________ alcohol.
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two, primary
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An ester can be reduced to an aldehyde only by using ___________________ at _________________ Celsius.
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DIBALH, -78
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A Michael reaction involves the attack of an ___________________ on a ________________ carbon of an a,b-unsaturated ketone.
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enolate, beta
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Michael reactions form ________________ diketones.
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1,5
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Enolates are ____________ bases and therefore add _________,_________.
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weak, 1,4
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The Robinson Annulation combines the _______________ addition and the _____________ reaction.
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Aldol, Michael
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The product of a Robinson Annulation is a _________,___________-_____________________ ketone.
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a,b-unsaturated
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Setting up for the Robinson annulation.
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Retro synthesis of Robinson Annulation
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Reaction of an aldehyde/ketone with a secondary amine forms a ________________.
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enamine
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Enamines resemble and react the same as _______________.
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enolates
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Aldehydes and ketones can be alkylated/acylated at the alpha carbon through an _______________ intermediate.
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enamine
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Using an enamine allows formation of a ___________________ alkylated product without using LDA.
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monoalkylated
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Enamine can also act as an enolate and attack the ________________ position of an a,b-unsaturated.
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beta
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The Diels-Alder reaction is a _________,__________ addition reaction.
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1,4
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A Diels-Alder reaction involves a conjugated _______________ and a ______________.
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diene, dienophile
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The reactivity of a dienophile is increased if an electron ___________________ group is attached to one of its sp2 carbons.
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withdrawing
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If the dienophile has two carbon carbon double bonds, _________________ successive reactions occur
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two
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What are the five common electrophilic aromatic substitution reactions
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1) halogenations 2)nitration 3) sulfonation 4) Friedel-Crafts acylation 5) FC alkylation
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The _____________ acidic the proton, the _____________ enolate is formed.
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more, more
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Acid catalyzed ester hydrolysis produces a
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carboxylic acid
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What is an enamine
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tertiary a,b-unsaturated amine
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What reagents are used to remove the enamine protecting group?
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acid and water
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In a Diels-Alder reaction, when the conjugated diene is in the locked s-cis cyclic position, the product is a _____________________ bicyclic compound.
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bridged
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Which is formed faster, the endo or exo product in a diels alder?
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Endo is formed faster when the dienophile has a substituent with pi electrons.
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What reagents are required to activate the electrophile for bromination
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Br2 + FeBr3
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What reagents are required to activate the electrophile in nitration
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HNO3 + H2SO4
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What is the electrophile in nitration reactions
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NO2+ (nitronium ion)
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What reagents are required to activate the electrophile for sulfonation
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H2SO4+ and heat
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What is the electrophile in sulfonation reations
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SO3H+ (sulfonium ion)
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FC acylation does what to a benzene ring
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places an acyl group on it
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What is the electrophile in a FC acylation
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acylium ion (R-C+=O)
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How is the electrophile for FC acylation activated?
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an acyl chloride (Cl) attacks the Al of AlCl3 and the Cl is then eliminated.
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What happens to primary carbocations?
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they rearrange
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How can a benzene substituted with a straight-chain alkyl group be formed?
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Through acylation reduction
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What are the three different sets of reagents used to reduce a carbonyl to a methylene group?
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1) H2 / Pd C 2) Zn(Hg), HCl, heat – acidic 3) H2NNH2, OH-, heat – basic
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Which reducing reagents can reduce all carbonyl compounds
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Clemmensen and Wolff-Kishner
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What are the reagents in the Clemmensen reduction
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Zn(Hg), HCl, heat – acidic
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What are the reagents in the Wolff-Kishner reduction?
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H2NNH2, OH-, heat – basic
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What is the stipulation to use H2 / Pd,C
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Only a ketone carbonyl adjacent to a benzene ring can be reduced
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What is the slow step of EAS?
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addition of the electrophile to the nucleophilic aromatic ring
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What will increase the rate of the slow step (addition of electrophile) of EAS?
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A substituent that makes benzene a better nucleophile (electron donating)
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The transition state of EAS resembles what?
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the carbocation intermediate
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What are moderately activating substituents?
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Can donate electrons in two directions. To the ring and away.
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What are moderately deactivating substituents?
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Carbonyl group attached to ring.
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What are strongly deactivating substituents?
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positive charge attached to ring
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What are strongly activating substituents?
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Donate electrons to ring only – OR attached
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What are halogen substituents?
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weakly deactivating
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All activating and weakly deactivating direct…
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ortho and para
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All substituents with a positive or partial positive attached to the ring direct _________________.
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meta
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The mirror image of a D-sugar is a ________ sugar
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L
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What is the Fisher projection of D-glucose
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What are epimers?
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Diastereomers that differ in configuration at only one asymmetric center
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What is the Haworth Projection of D-glucose?
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Groups on the Left in a Fisher are ____________ in a Haworth.
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up
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Groups that are Right on the Fisher are ___________ in a Haworth.
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down
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Two sugars that differ in configuration only at the carbon that was the carbonyl carbon in the open chain form are called ______________.
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anomers
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In the alpha anomer, the -OH group is ____________.
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down (trans to the primary alcohol)
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In the beta anomer, the -OH group is ____________.
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up (cis to the primary alcohol)
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In the Fisher projection, R equals ___________ and S equals __________.
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D, L
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To draw the Haworth, lay the Fisher down on its _________________ side.
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right
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The -OH on the number ____________ carbon attacks the carbonyl carbon.
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five
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What is the chair conformation of B-D-glucose.
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The acetal of a sugar is called a ______________.
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glycoside
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The bond between the anomeric carbon and the alkoxy oxygen is a ________________ bond.
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glycosidic
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What is the mechanism for a glycoside formation?
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Acetals are _____________________ sugars.
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non reducing
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What is an alpha-1,4-glycosidic linkage?
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What is a beta-1,4-glycosidic linkage?
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Acyl chlorides only react with alcohol and water
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Grignards do not react with ______________ or _______________.
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carboxylic acids, amides
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When you see an alcohol with 2 identical groups, think __________________.
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Grignard
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What reagent converts an alcohol into a carboxylic acid?
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What reagents synthesize an alcohol to an alkyl chloride?
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Thionyl chloride.
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What reagents synthesize an acid chloride from a carboxylic acid?
What reagents synthesize an acid chloride from a carboxylic acid?
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Thionyl chloride in pyridine.
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How does LiAlH4 react with benzoyl chloride?
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How does LiAlH4 react with acetic benzoic anhydride?
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How does LiAlH4 react with benzoic acid?
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How does LiAlH4 react with methyl benzoate?
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How does LiAlH4 react with benzamide?
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What product is formed when 2-bromohexane reacts with KCN, DMSO followed by H30+ and heat?
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What is the product of hydrolysis of an acid chloride?
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What is transesterification?
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What is the product of an acid anhydride treated with an alcohol under acidic conditions?
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What reagent(s) will reduce an ester to an aldehyde?
What reagent(s) will reduce an ester to an aldehyde?
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Di-Isobutyl Aluminum Hydride (DIBAH)
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How does butyramide react with ethanol in acidic solution?
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What reagents converts a ketone to an enolate? What is it used for?
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With an enolate, an alkyl substituent group can be added. LDA will alkylate on the less-hindered side of C=O.
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Show the synthesis of a carboxylic acid from a malonic ester.
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What is decarboxylation?
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Decarboxylation is the loss of CO2.
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What is an enamine?
What is an enamine?
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An enamine is an unsaturated compound derived by the condensation of an aldehyde or ketone with a secondary amine.
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What is the “Michael Reaction” and draw the mechanism.
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The “Michael Reaction” or “Michael addition,” is the nucleophilic addition of a carbanion or another nucleophile to an α,β unsaturated carbonyl compound. It belongs to the larger class of conjugate additions.
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Draw a mechanism for a base-catalyzed aldol condensation.
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Draw a mechanism for an acid-catalyzed aldol condensation.
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Draw a mechanism for the base-catalyzed dehydration of an aldol.
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What is an iminium salt intermediate and give a mechanism?
What is an iminium salt intermediate and give a mechanism?
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What is the product when ethenylbenzene is treated with KMnO4 and aq. NaOH?
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What is the claisen condensation? Draw a mechanism.
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A claisen condensation is a carbon-carbon bond forming reaction that occurs between two esters or one ester and another carbonyl compound in the presence of a strong base, resulting in a β-keto ester or a β-diketone.
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*ALKENE REACTIONS*
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*ALKENE REACTIONS*
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Hydration: Reagants
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Strong Acid, H20
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Hydration: Products
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Alcohol (Regioselective: Markovnikof)
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Oxymercuration/Demercuration: Reagents
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1. Hg(OAc)2, H2O 2. NaBh4, NaOH
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Oxymercuration/Demercuration: Products
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Alcohol (Regioselective: Markovnikof)
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Addition of a Hydrogen Halide: Reagents
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H-X
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Addition of a Hydrogen Halide: Products
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Alkyl Halide (Regioselective: Markovnikof)
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Hydrogenation: Reagents
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H2, Pt
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Hydrogenation: Products
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Alkane (Stereospecific: Syn)
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Cyclopropanation: Reagents
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Carbene
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Cyclopropanation: Products
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Cyclopropane (Stereospecific: Syn)
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Epoxidation: Reagents
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mCPBA
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Epoxidation: Products
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Epoxide (Stereospecific: Syn)
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Acid-Catalzyed Epoxide Ring Opening: Reagents
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H30
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Acid-Catalzyed Epoxide Ring Opening: Products
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Diol (Stereospecific: Anti) (A diol contains two hydroxyl groups)
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Syn-Dihydroxylation: Reagents
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OsO4, H2O2
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Syn-Dihydroxylation: Products
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Diol (Stereospecific: syn)
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Formation of a Halohydrin: Reagents
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X2, H2O
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Formation of a Halohydrin: Products
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Halohydrin ( functional group in which a halogen and a hydroxyl are bonded to adjacent carbon atoms) (Stereospecific: Anti) (Regioselective: Mark addition of -OH)
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Addition of X2: Reagents
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X2
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Addition of X2: Products
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Vicinal Dihalde (Stereospecific: Anti)
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Addition of HBr and Peroxides: Reagents
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HBr, H2O2
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Addition of HBr and Peroxides: Products
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Alkyl Bromide (Regioselective: Anti-Mark)
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Hydroboration/Oxidation: Reagents
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BH3,THF
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Hydroboration/Oxidation: Products
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Alcohol Stereospecific: Syn) (Regioselective: Anti-Mark)
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Oxidative Cleavage: Reagents
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KMnO4, Base
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Oxidative Cleavage: Products
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Ketones and Carboxylic Acids
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Ozonolysis, Reductive: Reagents
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O3, Me2S
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Ozonolysis, Reductive: Products
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Ketones and Aldehydes
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Ozonolysis, Oxidative: Reagents
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H2O2, AcOH
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Ozonolysis, Oxidative: Products
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Ketones and Carboxylic Acids
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Grignard: Reagents
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a. Mg, Ether b. Carbonyl c. strong acid *OR* a. LI Alkane, Ether b. Carbonyl c. strong acid
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Grignard: Products
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Alcohol (Regioselective: Reagent adds to the Carbonyl)
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*ALKYNE REACTIONS*
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*ALKYNE REACTIONS*
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Synthesis of Dihalides: Reagents
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NaOH, 200C *OR* NaNH3, H20
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Synthesis of Dihalides: Products
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Alkyne
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Acetylide Anion: Reagents
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Strong Nucleophile, H20
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Acetylide Anion: Products
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Alcohol
question

Oxidation of an Internal Alkyne: Reagents
answer

KMnO4, H2O
question

Oxidation of an Internal Alkyne: Products
answer

Dicarbonyl
question

Oxidation of an Terminal Alkyne: Reagents
answer

KMnO4, H2O
question

Oxidation of an Terminal Alkyne: Products
answer

Carboxylic Acid with adjacent Ketone
question

Hydrogenation (Alkyne): Reagents
answer

H2, Pd
question

Hydrogenation (Alkyne): Products
answer

Cis Alkene (Stereospecific: Syn)
question

Dissolving Metal Reduction: Reagents
answer

Na(s), NH3, low temp
question

Dissolving Metal Reduction: Products
answer

Trans Alkene (Stereospecific: Anti)
question

Ozonolysis: Reagents
answer

O3, H2O
question

Ozonolysis: Products
answer

Carboxylic Acids
question

Addition of HBr with Peroxides: Reagents
answer

HBr, H2O2
question

Addition of HBr with Peroxides: Products
answer

Vinyl Bromide (Regioselective: Mark)
question

Addition of X2 (Alkyne): Reagents
answer

X2, CH2Cl2
question

Addition of X2 (Alkyne): Products
answer

Dohalide/Tetrahalide (Stereospecific: Anti)
question

Addition of HX: Reagents
answer

HX, Ch2Cl2
question

Addition of HX: Products
answer

Dihalide/Tetrahalide (Regioselective: Mark)
question

Hydration (Alkyne): Reagents
answer

HgSO4, H2SO4
question

Hydration (Alkyne): Products
answer

Ketone (Regioselective: Mark)
question

Hydroboration/Oxidaton: Reagents
answer

SiaBH, H20, Strong Base
question

Hydroboration/Oxidaton: Products
answer

Aldehyde (Regioselective: Anti-Mark)

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