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Ch. 9 & 10

Alkyne naming, organohalides, more mechanisms

Reagents needed for HC triple-bond CH to form CH3CH2CH2CH2CH=O 1. NaNH2 / NH3 2. CH3CH2CH2Cl 3. BH3 / THF 4. H2O2 / KOH / H2O
Vicinal dihalide two halogens on neighboring carbons (example 1,2 diboroalkane)
True or false: carboxylic acids are more acidic than alkynes True
Free radical chlorination of methane, CH4 CH3(with radical) + Cl (with radical) --> CH3Cl
What is the reactivity order of alcohols with HCl (gas)/ether/0 degrees C? Tertiary > secondary > primary > methyl alcohols
monochlorination (Cl2/ uv light) of 1-methylcyclopropane form how many products? Forms 3 products!
Bromination (Br2/uv light) forms how many products? 1 product!
What product results from reaction of cyclopentene with NBS /CCl4 / uv light? 3-Bromocyclopentene
Allylic carbon carbon next to a double bond
Vinylic halide halogen on a double bond
Geminal dihalide halides attached to the same carbon
Alkyne + 2Br/CCl4 --> Tetrahalide product
Alkyne + 2H2/Pd, C --> Forms alkane
Alkyne + H2/lindlar catalyst --> Forms cis-alkene
Alkyne + Na/liquid NH3 --> Forms trans-alkene
Oxidative cleavage of a terminal alkyne Forms a carboxylic acid and a CO2
Oxidative cleavage of internal alkyne Forms two carboxylic acids
Oxidative cleavage reagents KmnO4/H+ or O3/Zn, H+
Rank alkyne acidity Alkyne > Alkene > Alkane
Why are alkynes more acidic than alkanes? Conjugate base of alkyne is stronger
Reagents of alkyne mercuration-demercuration... 1. HgSO4 2. H2O/H2SO4
Reagents of alkyne hydroboration... 1. BH3/THF 2. H2O2/KOH
How to rank hydrogens by increasing acidity Since acidity is directly related to the electronegativity of the central atom, the hydrogen atom attached to oxygen will be the most acidic, followed by the one attached to nitrogen, and then the one attached to sulfur.
When is a radical most stable? Allylic radical! (it is on a carbon that neighbors a double bond)
When is a radical least stable? Aryl radical (on a cyclo double bond) & vinylic radical (on a carbon double bonded to another carbon)
Best reagent needed to convert 2-methyl-1-pentanol into 1-chloro-2-methylpentane? SOCl2 / pyridine
alkene --> NBS/CCl4/uv light (list intermediate) --> KOH/heat--> (list final product) intermediate = bromine on carbon that neighbors double bond final product = 1,3 dialkene variant
Treatment of a cycloheptene with KMnO4 / KOH/H2O results in which of the following products? cis--1,2-diol
When an alkene is subjected to treatment with Hg(OAc)2 in CH3OH followed by reaction with NaBH4, what new class of compound is formed? ether
In the initiation step of the of free radical chlorination, what mechanism occurs? A Cl2 dissociates into two radical chlorines
In the first propagation step of the free radical chlorination of methane, what mechanism occurs? A chlorine radical abstracts a hydrogen (takes hydrogen away)
In the 2nd propagation step of the free radical chlorination of methane, what mechanism occurs? A carbon radical reacts with a chlorine radical
Describe the third step of free radical chlorination, termination radical + radical = molecule (two chlorine radicals make Cl2, to carbon radicals join, or a chlorine radical and a carbon radical join)
Alkyne to alkene with oxygen reagents... HgSO4, H2O, H2SO4
Alkyne to alkene reagents... 1. Br2 / CH2Cl2 2. excess NaOH / heat
Leaving group definition An atom or group of atoms which breaks away from the rest of the molecule, taking with it the electron pair which used to be the bond between the leaving group and the rest of the molecule
Bad leaving groups OH is the main one we focused on
Good leaving groups The conjugate bases of strong acids (e.g. I-, Br-, Cl-, TsO-, H2O) are good leaving groups
Created by: 2024032091273279
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