ch 10,11,14,15,16 Flashcards by Summer M

given mechanism name type of reaction and what it makes
“ cation pulls halide away ( K+ -> Br) and OH backside attacks to fill in where halide leaving group was”

Sn2 of alkyl halide for Oh synthesis

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Sn2 on alkyl halide to form OH produces what steriochemistry and why

flipped because the OH comes in through a backside attack and pushes the other group upwards

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Is acid catalyzed hydration a 1 step or 2 step reaction ?

2 step - carbocation intermediate

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does acid catalyzed hydration produce markovnikov or anti markovinov product and what would the product look like

Markovnikov, meaning the H will protonate on the less substituted carbon to create a more stable carbocation intermediate and then the OH will add on to the more substituted side

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what reagents can be used for an Sn2 alcohol production using an alkyl halide leaving group

any reagent that includes an electron poor electrophile such as K+ or Na+ and an OH group attached

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what reagents can be used for acid catalyzed hydration of an alkene ?

any strong acid and H2O

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what sterio-chemistry will acid catalyzed hydration create on a regular alkene as well as a fully substituted alkene ( syn or anti)

a racemic mixture of both syn and anti addition when both sides of the alkene are substitued otherwise it follows markovnikov

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what reagents are used for oxymercuration demercuration

first HgOAc2 and then NaBH4

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is oxymercuration markovnikov or anti markovnikov

markovinkov

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what is unique about the intermediate in oxymercuration

the Hg forms a 3 membered ring with the two carbons after the alkene is broken

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what reagents are used for hydroboronation

BH3 paired with a THF solvent

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is hydroboronation markovnikov or anti

anti markovnikov

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does hydroboronation produce syn or anti addition

syn addition meaning the added H and OH will be both out or down

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what is the difference between cis/trans, E/Z and syn/anti

-cis and trans refer to whether an element shares the same steriochemistry such as both being up ( wedges) or both back ( dashes)
- E and Z refer to the priority level groups on either side of a double bond being on the same or different sides of of the double bond
- syn and anti refer to the way that the groups are added into the chain, if they are added with the same steriochemistry they are syn, different would be anti

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what are the two reagents for hydroxylation

KMnO4 and OsO4 with H2O2

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what does hydroxylation produce and in what kind of addition ( syn/anti)

produces a syn addition diol through an epoxied intermediate

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what is an aldehyde

C with pi bond O, an R group and H group

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when a tertiary alcohol is oxidized with a strong oxidant what is the result

tertiary alcohols are resistant to oxidation

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when a secondary alcohol is oxidized with a strong oxidant what is the result

ketone

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when a secondary alcohol is oxidized with a weak oxidant what is the result

ketone

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when a primary alcohol is oxidized with a strong oxidant what is the result

carboxylic acid

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when a primary alcohol is oxidized with a weak oxidant what is the result

aldehyde

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what are the most common weak oxidants

PCC, DMP, swern oxidation (DMSO,COCl2), Cr2O3/pyradine (collins)

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what are the most common strong oxidants

Chromic acid (H2CrO4)
KMnO4
H2CrO4/acetone ( jones)
HNO3 ( nitric acid)

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what is the purpose of the tosylate mechanism

to create a better leaving group for substitution and create full stereochemistry inversion and not a mixture

HBr and HCl result in what kind of stereochemistry

racemic mixture

the use of tosylate results in what kind of of stereochemistry

complete inversion not racemic

what is TsCl/ pry

tosylate mechansim

what is the the tosylate intermediate

OTs

When an OH group is protonated, it creates a better leaving group and a halide can come replace it in a substitution reaction - a primary alcohol will undergo ( SN1/SN2) - a secondary alcohol will undergo ? - a tertiary alcohol will undergo ? and why ?

Primary OH - Sn2 concerted substitution because the C that it is attached to would not be stable enough to form a carbocation intermediate - 2 and 3 OH will undergo Sn1 because the 2 and 3 carbocation intermediates are table enough to exist

why would you not want to use a hydrohalogenation ( HX) reagent

- elimination competes with substitution

What are the phosphorus halide reagents

PBr3 PCl3 ( SOCl2) P & I2

does phosphorus halide reagents result in retention or inversion of steriochemistry

Phosphorus halide reagents ( PBr3, SOCl2) will result in inverted stereochemistry

when using a phosphorus halide reagent (PBr/SOCl2), what kind of reaction will ensue (Sn1/Sn2/E1/E2 )

Sn2

what are the resulting products of the phosphorus halide substitution

with PBr3 - alkyl bromide and leaving group of OHPBr2 with SOCl2 - alkyl chloride, HCl and SO2

what are the 2 common reagent used in a dehydration reaction

H2SO4 and POCl3what

what are the major steps of a dehydration reaction

Protonation H2O leaves deprotonation of H ( possible rearrangement) formation of pi

what mechanism does the dehydration reaction follow ( SN1/SN2/E1/E2)

typically E1 because of potential for rearrangement

what is often the result of a dehydration reaction

pi bond

why does a pi bond form through dehydration

H is deprotonated off of the C next to carbocation and the electrons from H bond shift into a pi bond to stabilize the carbocation

what is pinacol dehydration

dehydration of a diol to form a ketone using any strong acid and heat

what is the pinacol dehydration mechanism

one of the OH is protonated to make a H2O leaving group, a carbocation is formed, shifts occur to stabilize, the other OH is deprotonated creating a C=O bond aka ketone

what does periodic acid do as a reagent (HIO4)

cleaves glycol ( C-C bond each with an OH) into ketone or aldehyde (depending on substituents)

what is fisher esterification

alcohol and carboxylic acid combined to form ester and water

why isnt fisher used often

creates an equilibrium of products and reactants

what is the product of R-OH and acyl chloride (carbonyl with Cl on one end)

ester and HCl ( used similar to fisher)

what is the most common nitrate ester reaction

glycerol --> nitroglycerine

what are the reagents to make a phosphate ester

phosphoric acid and methoxide (CH3O)

what is LiAlH4 used for as a reagent

reduces carbonyl groups to alcohols

what is the major difference between using LiAlH4 and NaBH4 as reducing agents on carbonyl groups

LiAlH4 is a strong reducing agent while NaBH4 is a weaker reducing agent

what reducing agent is often used for aldehyde and ketone

weaker reagent, NaBH4 & H3O+

what reducing agent is needed for ester and carboxylic acid

strong reagent, LiAlH4 and H3O+

what is an aldehyde reduced to

primary alcohol

what is a ketone reduced to

secondary alcohol

what are esters and carboxylic acids reduced to

primary alcohols

what is added to the C=O after a grignard reagent reaction

the C=O bond results in a C with OH, and the alkane group that was added as a racemic mixture because the reagent can add in the top or the back

would ch3-O-ch3 or ch3)2-O-Ch3)2 have a higher boiling point

Ch3)2-O-CH3)2 would because the substituents are larger

what kind of bonding can ethers undergo

h-bonds with water and alcohols

what kind of molecules would ethers make a good solvent for

cations and larger anions

what is a crown ether and what is its purpose

a circular network of ethers that can surround metal cations to dissolve them in nonpolar organic substances that may not be able to dissolve them alone

how are epoxides named

alkane plus oxide at the end, as a epoxy substituent, or as the parent with O being 1 naming substituents and ending in oxirane

what would happen if the alkoxide ion reacted with a secondary or tertiary halide

an elimination reaction and would take the halide and leave an alkane group

what does HCCNa do as a reagent

creates a triple bond out of a halide/leaving group

what does M-CPBA reagent do

create epoxide ring on double bond

can grignard reagent react with epoxide

yes, the O is protonated to OH and stays on the more substituted side and the alkyl group is added to the end

what does NaNH2 do as a reagent

acts as a strong base for halide elimination

how are thioethers synthesized

with a thiol reagent ( S-R ), substitutes a halide

does thioether synthesis change stereochemistry

yes, inversion occurs

when halide substitution takes place on a cyclic molecule with other substituents, what is the resulting stereochemistry

halide substitution results in inverted chemistry but ANY OTHER SUBSTITUENT NOT INVOLVED IN THE SUBSTITUTION IS NOT CHANGED

ch 10,11,14,15,16 Flashcards

(70 cards)