Chemistry MCAT about alkanes, alkenes, alkynes , amines .. flashcards

Title: Chemistry MCAT about alkanes, alkenes, alkynes , amines .. flashcards
Description: Chemistry with alkanes, alkenes, alkynes,alcohols, amines
Potrait:  2x4  1x2  4x8    Landscape:  4x4  2x2  6x6
1In order to produce a 1'amide, an acid chlorid should be treated with ammonia
2What is the best method of producing methyl propanoate? Propanoic acid + methanol in the presence of a mineral acid
3what does an sn2 do to the chirality of a compound?it flips it.
4a polar aprotic solvent favors?SN2
51>2>3 is favored in ?sn2
63>2>1 is favored in ?sn1
7sn1 rate=k[RX]
8sn2 rate=k[Nu][RX}
9SN2 do what to optical activ?it will cause an inversion of configuration
10Bulky nucleophiles favor?sn1
11alkynes reduct with sodium in liq ammonia bel -33 yields?trans isomer of alkene
12alkyne reduct with sodium and ammonia occurs thr what mech?free radical mechanism
13electroph addit to alkynes occurs in a ___________ manner?markovnikov's
14electroph addit to alkynes can be stopped at _______________________ or carried furtherintermediate alkene
15free radi cal addit to alkynes add with ___________________ orientationanti- markovnikov
16free radical addit to alkyne intermediate vinyl radical can?isomerize to its more stable form
17alkynes can be ________________ with B2h6hydroborated.
18hydroboration of alkynes is?syn, boron atom adds first
19hydroboration of triple bonds the boron atom can be replaced with a proton from?acetic acid
20hydroboration of alkyne. boron atom can be repl with a proton from acetic acid to make a ?cis alkene
21methanol is _________ alcoholwood
22methanol is toxic and can cause?blindness
23alcohols can be prep via?1. addit of water to double bonds 2. addit of organometallic comp to carbonyl gr
24alcoh can be made by reducing?aldehydes, ketones, carboxylic acids, esters
25aldehydes, ketones, carbox ac, esters can be red to?alcohols
26to reduc aldeh, ketones, carb acids, esters to alcoh you use?LiAlH4, LAH, NaBH4
27LAH is?lithium aluminum hydride
28NaBH4 is?sodium borohydride
29LAH and NaBH4 which is more powerful and diff to work with?LAH
30LAH and NaBH4 which is more selective?NaBH4
31making a cyclic ether internal sn2 react why is this favored?bec the nucleoph and leaving gr are foced into high conc w each other bec they are on the same molec
32in air ethers react w O2 to form?peroxides ROOR
33ROOR is the formula for?peroxides
34ethers + ? will form peroxidesO2
35cleavage of straight chain ehters needs?vigorious condit high temp w HBr and HI
36cleavage of an ether is started by?protonation of ether oxygen
37cleavage of an ether why do you need to protonate the ether oxy?bec otherwise the leaving gr is alkoxide which is strongly basic and a bad leav gr
38cleav of an eth ether will bec ?it will split and end up as 2 alkyl halides
39what reagent do you need to cleave an ether?high temp, HBr, HI
40cleav of an ether with high temp , HBr, HI makes?an alkyl halide and an alcohol the alcohol w furth react and make anoth alkyl halide
41What is saponification?The process where fats are hydrolyzed to produce soap.
42Saponification takes place under acidic/basic conditions.Basic
43What is transesterification?When a different alcohol attacks an ester.
44Grignard + Ester =Ketone
45What is Claisen condensation and what is it also known as?The process whereby the enolate ion of one ester acts as a nucleophile, attacking another ester. AKA acetoacetic ester condensation.
46Esters may be reduced to 1' alcohols with what? LAH
47RCOOH + SOCl2, PCl3, PCl5 or PBr3 =acyl halide
48These participate in Friedel-Crafts acylation to form an alkyl aryl ketone.Acyl halides
49Esters + 2 Grignard =3'ROH
50During the hydrolysis of an acid chloride, pyridine (a base) is usually added to the reaction vessel b/cit acts as a base and serves to neutralize the HCl that has formed.
51when the nucleoph attacks the react from the backside what is formed?a trigonal bipyramidal trans state
52SN2 follows _____________ kineticssecond order
53the rate of SN2 react dep on the concentr of?2 reactants
54what things do you have to take into account for SN1 vers SN2?1. sterics 2. nucl str 3. leav gr ability 4. react condit 5. solv effects
55sn1 vers sn2 when you see H+ above the arrow think of?cationic mech like Sn1
56Sn1 has a ____________ intermedtrigonal planar
57Sn1 vers sn2 the carbocation is chiral or achiral?achiral
58Sn1 res in a _______________ of optical activloss of
59Sn1 will turn an optically active comp into a?racemic mixture
60sn2 has a ______________ transition statechiral
61general formula for alkene is?CnH2n
62degree of unsaturation means?how many double bonds it has
63N=1/2(2n + 2-m) is used to determ?the degree of unsaturation
64what formula do use to determ degr of unsat?N=1/2(2n + 2-m) based on molec CnHm
65alkenes are ______________ react than alkanesmore
66alkenes are also called?olefins
67what terms can you use to describe alkenes?cis, trans, e and z
68ethylene is?ethene
69propylene ispropene
702 methyl 1 - propene is?isobutylene
71alkynes have ______________ and can be slightly polardipole moments. but still pretty small
72terminal alkynes are ?acidic
73triple bonds can be made by?1. eliminat of 2 HX from geminal or vicinal dihalide 2. addit of exist triple bond to a nucleophile
74eliminat of 2 HX req?high temp and str base
75how do conv a term triple bond to a nucleophile?by remov acidic prot w a str base to prod an acetylide ion
76acetylide ion is used to?add an exist triple bond to carbon skeleton
77partial hydrogenation of triple bonds occurs in what 2 ways?1. lindlars catalyst to make cis isomer 2. sodium in liquid ammonia bel -33 to prod trans isomer of alkene
78reduct of alkynes LIndlars catalyst is?palladium on barium sulfate BaSO4 with quinoline
79reduct of alkynes lindlars catalyst what does quinoline do?its a poison that stops the react at the alkene stage
80alkynes reduct with lindlars catalyst prod?alkene with cis isomer
81__________ will reduce carboxy ac and esters to alcohLAH
82___________ will not reduce carbox ac and esters to alcohNaBH4
83maing phenols w arylsulfonic ac with hot NaOH whats the disadvant?it will destroy most funct gr other than the phenol gr and its alkylated deriv
84how do you make phenols?with arylsulfonic ac and hot NaOH
85whats a better way of making phenols than by using arylsulfonic acids with hot NaOH?hydrolysis of diazonium
86hydrolysis of diazonium uses what reagants?HNO2/HSO4 followed by H3O
87hydrolysis of a diazonium salt will turn an aromatic NH2 gr into a?OH group
88an alcoh can be made into an alkene suing?a strong acidic solution
89alcohol---- alkene this process of getting rid of the alcoh is called?dehydration
90the mech of dehydration of an alcoho is?E1 and goes thr a protonated alcohol
91cleavage of a straight ch ether is acid
92t or f cleavage of cyclic ethers can be acid or base catalyzedtrue
93epoxides easily undergo what kind of react?Sn2
94why do epoxides easily undergo SN2 react?bec they are highly strained
95epoxide SN2 react can be catalyzed by ________ or _____________acid or base
96epoxide asymmetrical epoxide which carbon is nuclephilically attack? in pres of acid?the more subst c
97epoxide. in pres of base which c is nucl att?the least subs c
98base catal cleav has the most ____________ charactSN2
99epoxid cleav which catal react has most SN2 charact? acid or basebase
100cleav of epoxide acid catal has some _________- charactSN1
101mp and bp of alkenes?incr w incr molec weight
102trans alkenes have ________ mp than cis alkeneshigher
103why do trans alkenes have higher mp than cis?they are more symmetr
104trans are less __________ than cis alkenespolar
105cis alkenes have higher bp than trans alkenes due to>?polarity
106in an alkene the _____________ is electroneg and the ________ are electropodouble bond is electroneg alkyl gr are electropos
107in trans 2 -butene the dipole moments?cancel each other out
108t or f cis 2-butene has a net dipole momenttrue
109synth of alkenes most common way of synth?elimination react of alc or alkyl halides
110what 2 things are commonly elimin to make alkenes?1. alc 2. alkyl halides
111hydroboration what do you do with terminal alkynes?use a disubstituted borane to prev further boration of vinylic intermediate to an alkane
112hydroboration of alkynes term alkyne-use disubst borane. VInylic borane interm can be?oxidately cleaved with hydrogen peroxide
113H2O2 is?hydrogen peroxide
114hydroboration of term alkyne the interm vinyl alcohol rearranges to make?more stable carbonyl compound
115hydroboration of term alkyne intermediate vinyl alcohol rearranges to more stable carbonyl compound via?keto-enol tautomerism
116alkyes can be oxidatively cleaved with?1. basic KMnO4, acidification 2. ozone
117oxidat of alkynes will yield?carboxylic acids
118alcohols are usually dehydrated with ?H2SO4
119alcohol dehdrat will have 2 prod. what will be the maj one?the more stable alkene. occurs thr movement of a proton to prod the more stable second carbocat
120E1 you want to form the most stable?carbocation
121displac of hydroxy gr in subst react is rare bec?hydrox ion is a poor leav gr
122to displace a OH gr you have to?make it a good leaving gr by protonating it to make H2O
123by protonating an alcohol you make it?a good leav gr
124a protonated alcohol is good for a _____________ reactSn1
125alcohol conv to tosylate (p-toluenesulfonate) gr is a good leav gr for a ___________ reactSn2
126what 3 ways can you turn an alchol into a good leav gr for an Sn1/Sn2 react?1. protonate it 2. conv it to tosylate 3. form an inorg ester
127alc to alky halide you change the alc to a?inorganic ester. which will then do SN2
128general formula for an ether is?ROR
129you can think of ether as being a disubstituted ?water molec
130diethyl ether can be used as ?medical anesthetic
131IUPAC ethers are named as?alkoxyalkanes
132IUPAC ethers smaller chain is?alkoxy
133IUPAC ethers larger chain?is named as suffix
134Common naming of ethers use?alkyl alkyl ethers
135methoxyethans common name would be?ethyl methyl ether
136oxirane is also called?epoxide
137name 3 cyclic ethers?oxirane oxyethane oxacyclopentane
138Anhydride + H20 =RCOOH
139Anhydride + NH3 =Amide + ammonium carboxylate
140Anhydride + ROH =RCOOR + RCOOH (Ester + Carboxylic acid)
141Amides can be hydroylzed under acidic conditions to produce... RCON + H20 =Carboxylic acids which occurs via nucleophilic substitution
142What is the Hoffman Rearrangement?Conversion of amides to 1'amines through the loss of a carbonyl carbon
143The nitrogen equivalent of a carbene called a ______________ is a step in a ______________.Nitrene/Hoffman Rearrangement where a amides are converted to 1'amines.
144Amides are reduced with LAH to yieldamines
145Acid + alcohol =Ester. Esters are the dehydration products of RCOOH and ROH.
146According to the IUPAC system esters are named as...alkyl or aryl alkanoates.
147What are triacylglycerols?Esters of long chain carboxylic acids and glycerol. AKA fats
148sn2 avoids forming a?carbocation
149SN2 is a ?bimolecular nucleophilic substitution
150describe an SN2 reaction?nucleophile pushes its way into a compound while displ the leaving group
151how many rate determ steps does SN2 have?one
152SN2 the rate determ step involves?2 molecules. substrate and nucleophile
153for SN2 you need a strong __________________?nucleophile
154t or f a transition state really exists?false
155an intermediate is a?well defined species with a finite lifetime
156which is real and actually exists? a. intermediate b. transition statean intermediate
157For SN2 the reactant can not be?sterically hindered
158Why does the proton add to the less subst carbon atom?bec alkyl subst stab carbocat
159addit of HX markovnikovs rule says thatproton will add to least substituted carbon, X will then add to more subst carbon atom
160alkenes addition of hx PROTON WILL ADD TO ?less substituted atom
161Markovnikov's rule says that ?a halide, oh-, etc will add to most subst c in double bond
162alkenes addition of X2 is a ______________ processrapid
163what chemical react is used to test for presence of double bonds?addition of X2
164in addition of X2, the double bond acts as a?nucleophile and attacks an X2
165in addition of X2, the intermediate carbocation forms a ?cyclic halonium ion.
166addition of X2 is syn or anti?anit. X- attacks cyclic halonium ion in Sn2 fashion
167addit of X2 in nucleophilic solvent what can happen?solv molec can comp in displ step. prod halo alcohol (and not a dihalo compound)
168oxiranes are also called?epoxides
169mcpba is ?m-chloroperoxybenzoic acid
170how do you make an oxirane?alkene plus CH3CO3H or mcpba
171polymers are?long chains called polymers of repeating subunits.
172the repeating subunits of polymers are called?monomers
173polymerization occurs thr what mechanism?radical
174give a typical example of polymerization?formation of polyethylene from ethylene (ethene) req high temp and press
175CH2=CH2 with R*, heat, high press will make?RCH2CH2(CH2CH2)n CH2CH2R a polymer
176ethyne is called?acetylene
177suffix _________ is used for triple bonds-yne
178ROH alcohols are weakly?acidic
179strong acids have ___________ Ka'shigh
180strong acids have _________ pKassmall
181the hydroxyl gr of _________ are more acidic than alcoholsphenols
182the hydroxy gr of phenols are more acidic than alcohols due to ?resonance struct that distr negat ch thr the ring.
183for alcohols electr donating gr ______________ the alkoxide aniondestabl
184acidity ____________ as more alkyl gr are attacheddecre
185why does acidity decr as more alkyl gr are added to an alcohol?bec electr donat alkyl gr destab the alkoxide anion
186__________ stabilize the alkoxy anion, mak the alcoh more acidicelectr withdraw
187what kind of gr make the alcohol more acidic?electr withdraw
188epoxide cleav acid protonates the epox O and makes it?a better leaving gr. this gives the c a bit of a posit ch.
189acid cat cleav of epox protonation of O makes the carbons?a little bit positive
190key react of ethers?1. epoxide format 2. SN1 AND sn2 REACT
191williamson eth synth the substrate cant be highly substituted but the attacking alkoxide?can be highly substituted
192t or f williamson ether synth can also be used w phenolstrue
193williamson eth synth why do you only need mild react condit?bec the phenol is more acidic
194cyclic ethers are prepared via ______________ mechanismSn2 internal displacement
195to make a cyclic ether, the _________ and the __________ are part of the same moleculenucleophile leaving gr
196oxidat of an alkene with _________ will produce a oxiraneperoxy acid like mcpba
197RCOOOH is a?peroxy acid
198mcpba is a?peroxy acid
199MCPBA stands for?m-chloroperoxybenzoic acid
200alkene + mcpba will make?an oxirane
201Explain reductive amination.A process where an aldehyde or ketone reacts with NH3 to produce and imine which is then reduced to an amine.
202How are amides reduced to amines?via LAH
203Explain the Hoffman elimination.Amine is converted to quarternary ammonium iodide via excess MEI then treated with Ag2O/H2O to an ammonium hydroxide which is then heated to produce an alkene + trisubstituted amine.
204The reaction of benzamide with LiAlH4 yields... benzylamine
205Which of the following has the highest boiling point? CH3(CH2)6NH2
206If 2-amino-3-methylbutane were treated with excess methyl iodide, silver oxide, and water what would be the major rxn products? trimethylamine and 3-methyl-1-butene
207What is the predominant alkene product in a Hoffman Elimination?The least substituted alkene.
208form alkenes you lose?1. HX 2. H2O
209alkenes eliminat occurs by either?E1 E2
210E1 proc thr a ?carbocat intermediate
211E1 the carbocation is a intermed
212E1 rate of react is depend on?substrate
213descr 2 steps of E1?1. leav gr leaves, carbocat is formed 2. proton is remov by base
214E1 is favored by?highly polar solv branch carbon ch good leav gr weak nucleph in low concentr
215What mech is competit with E1?Sn1
216E1 and Sn1 are similar in that?they are favor by the same factors
217T or F low temperat favor E1False
218alcohols plus what will make an intermed inorgan ester and HCL?thionyl chloride
219Thionyl chloride is used to?make an alcohol into an inorg ester and then an alkyl halide
220SOCl2 is?thionyl chloride
221thionyl chloride is?SOCl2
222to make an alc into a alkyl bromide you react alc w?PBr3
223phenols undergo electr aromatic?substit react. it has lone pairs it can donate to the ring
224phenol OH gr is __________, ___________ direct ring conststrongly activating ortho/para direct
225t or f phenols are good subst for electr aromatic substtrue
226oxid of alcohols usually is done with?some form of chromium (VI)
227primary alcohols to aldehyde is done w?PCC
228Name 3 Carboxylic Acid Derivative reactions that involve nucleophilic substition.1. Hydrolysis 2. Ester conversion 3. Amide conversion
229Acid halide + H2O =RCOOH (carboxylic acid)
230Acid Halide + ROH =RCOOR (ester)
231Acyl Halides + NH3 =Amides
232Friedel Crafts Acylation takes place via nucelophilic/electrophilic substition on an aromatic ring.Electrophilic aromatic substitution
233Acid halides can be reduced to alcohols or selectively reduced to intermediate aldehydes viaH2/Pd/BaSO4 Quinoline
234The most common and important anhydride that is a dimer of acetic acid isAcetic anhydride
235Anhydrides are formed via2 acid molecules condensing(losing water)
236Name 3 ways in which anhydrides can be made:1. RCOOH + RCOOH 2. Acid chloride + carboxylate salt 3. Heating
237Certain cyclic anhydrides can be formed simply by heating carboxylic acids. This reaction is driven by...the increased stability fo the newly formed ring hence only 5 or 6 membered rings are EASILY formed
238E2 vers Sn2 weak lewis base fav?SN2
239what things do you modif to fav E2 over E1 and Sn1?1. pol of solv 2. branch of carbon ch
240name react of alkenes1. polymerization 2. oxid alkenes to form oxiranes 3. ozonolysis of alkens to cleave double bond 4. oxidat of alkenes w KMnO4- 5. hydroboration with diborane B2H6 and peroxide to make an alcohol 6. adding HX to alkenes thr free radic 7. addit of H2O under acidic condit 8. addit of X2 (halogens) 9. addit of HX 10. reduct using metal catalyst
241alkenes can be _________ with molec hydrogen and metal catalystreduced
242Catalytic hydrog needs?hydrog and metal catalyst
243reduct of alkenes typical catalysts are?platinum, palladium, Raney nickel
244Raney nickel is a ?special powdered form of nickel
245Reduct of alkenes is a __________ additsyn
246in reduct of alkenes the 2 hydrog are added to?same face of double bond
247react where one sterioisomer is favored are called?sterospecific reactions
248oxidat of alkenes with KMnO4 in cold, dilute produces?1,2 diols (vicinal diols)
2491,2 diols are also called?vicinal diols, glycols
250oxidat of alkenes with potassium permanganate (cold, dilute) makes?1,2 diols (vicinal diols) with syn orientation
251hot basic solut of potassium permanganate, then acidified, what happens to alkenes?1. non term alkenees are cleaved to make a 2 molar equiv of carboxylic acids 2. terminal alkenes are cleaved to form carboxylic acid and carbon dioxide 3. nonterm bond that is disubstituted will yield ketone
252With reagants 1.KMnO4, OH-, heat 2. H+ what happens to alkenes1. carboxylic acids are prod 2. term double bond prod carbox acid and CO2 3. nonterm double bond w disubst carbon will make ketone
253ozonolysis of alkenes uses what reagents?1. O3, CH2Cl2 2. Zn/H2O
254ozonolysis of alkenes with ozone and then reduced with zinc and water will prod?the double bond will split and yield aldehydes
255what will this do to an alkene? 1. O3, CH2Cl2 2. NaBH4, CH3OHsplit the double bond and make alcohols
256alkens pxid with ___________ yield oxiranes (epoxides)peroxyacetic acid
257alkens and CH3CO3H or mcpba will yield?oxiranes
258phenols can _______ with inorganic bases like NaOhform salts
259what are the 3 big mech for alcohols?1. Sn1, Sn2 nucl subst 2. electr addit to doubl bond 3. nucl addit to carbonyl
260CH3Br + OH- ----> CH3OH + Br- this is a ?nucleophilic substition
261aloohols can form from _____________ to a double bondelectrophilic addit to a double bond
262an alcohol can form from a __________ to a carbonylnucleoph addit
263levels of oxidation primary alcohos----- ? ----carboxylic acidsaldehydes
264oxidat levels second alcohols---- ?ketons
265who is more oxidized an aldehye or a carboxylic acid?carboxylic acid
266more bonds to ________ means more oxidizedoxygen
267methanol can be made by destruct distillation of?wood
268oxacyclopentane is also called?tetrahydrofuran
269smaller rings have more _____________, making them less stableangle strain
270t or f ethers do hydrogen bondingfalse
271ethers bp are ?similar to alkanes
272ethers solub in water?only slightly sol inert to most organic reag
273metal alkoxides w prim alkyl halides or tosylate will make?ethers
274williamson ether synth makes ethers from?metal alkoxides w prim alkyl halides or tosylates
275williamson ether synth metal alkoxides act as?nucleophiles
276williamson ether synth acts via a ___________ mechanismSN2
277williamson ether synth since its SN2 you need?a strong nucleophile (like alkoxide) unhindered substrate (not bulky or highly subst)
278What is a nitrogen atom attached to four alkyl groups called?Quarternary Ammonium Compound
279Since the nitrogen carries a positive charge, amines usually exists assalts
280In the common system, amines are generally named as alkylamines but in the IUPAC system the suffix _______ and prefix __________ are used.suffix- amine prefix- amino (used for naming compounds containing OH or CO2H groups)
281What is the IUPAC name for amines that are derivatives of aniline?Benzenamine
282What are carbamates?Compounds with the general formula RNHC(O)OR'
283What are carbamates also known as?urethanes (which can form polymers called polyurethanes)
284What are carbamates derived from?Isocyanates (RNCO) + ROH
285What is an enamine?Nitrogen analog of an enol with amine group attached to one end fo double bond C=C-N
286What is an imine?Molecule with C=N double bond
287What are nitriles?Compounds with carbon-nitrogen triple bond.
288High or low temper which favor E1high temperatures
289E2 occurs in how many steps?one
290E2 rate is depend on?concentr of substr and base
291in E2 a _____________ removes a proton and a halide ion ________ to the proton leavesstrong base rem halide ion anit
292In E2 the _______________ double bond is preferredmore subst double bond
293It is easier to control ______________ than E1 vers Sn1E2 vers Sn2
294E2 is not affected by?steric hindrance
295SN2 is affected by ?steric hindrance
296Highly subst carbon chains will undergo E2
297SN2 vers E2 strong base fav?E2
298addition of X2 in what can make a halo alcohol?nucleophilic solvent
299addition of H2O. water can be added to alkenes under?acidic conditions
300addition of H2O follows what rule?markovnikov rule
301addition of H2O OH will add to ?more subst c of double bond
302addition of H2O is performed at low temp
303why is addit of h2O perf at low temperat?bec otherwise the reverse react will happen. (acid catalyzed dehydration)
304what is the reverse react of addition of H2O to alkeneacid catalyzed dehydration
305addition of H2O is carried out indirectly because?bec yield varies w concentration
306How is addit of H2O carried out indirectly?using mercuric acetate Hg(Ch3COO)2
307what is Hg(Ch3COO)2mercuric acetate
308PCC ispyridium chlorochromate
309C5H6NCrO3Cl is ?PCC
310PCC will make what from an alcholo?aldehyde
311alcohol plus PCC will make?aldehyde
312alcohol + PCC will not overoxidize to?an carboxylic acid
313oxid of alc PCC versus KMnO4KMno4 will oxid to carboxy acid
314PCC can make secod alc into?ketones
315PCC and also ___________ can both be used to make second alcholosalkali dichromate salt
316alcohol + sodium dichromate salt ----->carboxy acid
317when you see a transition metal like Cr or Mn with lots of oxy think of?oxidation
318electroph addit of alkenes which bond is weaker?pi bond
319Electr on pi bond and are attacked by ?lewis acids
320in electr addit of alkenes lewis acids attack?pi bond
321lewis acids want to accept?an elect pair
322lewis acids are ______________electrophiles
323alkenes addit of HX electr of double bond act as?lewis base
324alkenes addit of HX first step yields a?carbocation
3252 steps of addit of HX to alkene?1. double bond reacts w proton 2. halide ion comb w carbocat
326in addit of HX proton adds to form the most?stable carbocat
327addit of HX proton adds to the ?less subst carbon atom
328Free radical addition of HX occurs when?peroxides, oxygen, or oth impurities are pres
329Free radical addit of Hx __________ THE MARKOVNIKOV ruledo not follow
330Why dont free rad addit of HX follow the markov rule?bec the X* (radical) adds first to the double bond. making the most stable free radical
331free radical addit to alkenes is useful for which halides?HBR, but not HCL, or HI
332Hydroboroation involves use of ?diborane (B2H6)
333Hydroboration. Diborane. the boron atom is a ?lewis acid
334hydroboration occurs accord to ?antimarkov, syn orientation
335what are the 2 steps of hydroboration?1. addit of boron atom to less ster hind carbon 2. oxidat-hydrolysis w peroxide and aq base
336what reagents are needed in hydroboration?BH3, H2O2, OH-
337oxidation of alkenes is done with?KMnO4
338ROH arealcohols
339-OH is?hyroxyl group
340alcohol can be thought of as a subst ____________water molecule
341iupac system alcohols are ?ol
342because the -OH gr has high priority, its carbon must be?in the carbon backbone with the low numb poss
343ethanol can also be called?ethyl alcohol
344ArOH is called?phenol
345bp of alcohols are signif are higher than alkanes bec?hydrogen bonding
346the more hydroxy gr a molec has the more ?hydrogen bonding
347hydrogen bonds form on the "phone" the "fon" means?h with F, O, or N will make hydrogen bonds
348Cr2O7, Cro3, MnO4 when you see these, think of?oxidation
349Na2Cr2O7 is?sodium dichromate salt
350second alcohol plus Na2Cr2O7/H2SO4 will make aketone
351CrO3/H2SO4/acetone is __________ reagentJones reagent
352Jones reagent is?CrO3/H2SO4/acetone
353primary alc + CrO3/H2SO4/acetone --->carboxy acid
354second alcholo +CrO3/H2SO4/acetone --->ketone
355phenols plus oxidizing reagents will make?quinones. which is a benzene gr with c=O on it.
356ether is2 alkyl or aryl gr bonded to an oxy
357ROR is a?ether
358What are nitriles also known as?Cyanides
359Nitriles are named with the prefix _________, and the suffix __________.Prefix- Cyano Suffix- nitrile
360What are diazo compounds?They contain a N2 functionality. Ex. C=N=N
361What are azide compounds?They contain N3 functionality. Ex. N=N=N
362Why do 3' amines have lower boiling points than 1' or 2'?Because they can not form hydrogen bonds.
363Why are aromatic amines less basic than aliphatic amines?B/c the electron withdrawing effect of the ring reduces the basicity of the amino group.
364What is the Gabriel synthesis?Converts a 1'alkyl halide to 1' amine.
365The Gabriel synthesis occurs via SN1/SN2 E1/E2.SN2
366How are nitro compounds reduced to 1' amines?The most common reducing agent is Fe or Zn in dilute HCL and they reduce NO2 - NH2
367How are nitriles reduced to 1' amines?They are reduced with hydrogen and a catalyst or LAH.