Chapter 10 Flashcards
The bond angle between H-O-H in water is _____
104.5
The bond angle between C-O-H in methyl alcohol is _____
108.9
When naming alcohols: drop the final e in the alkane name and replace with ___
ol
The longest carbon chain MUST be attached to the functional group _______, then # the chain so as to give that group priority
Winner (-OH)
The OH group is treated as a substituent named _______ when it appears on a structure with a higher priority functional group
hydroxy
alcohols with two -OH groups are called _______. They are named like other alcohols except that the suffix diol is used and 2 numbers are needed to tell where the two hydroxy groups are located
diol or glycol
- needs e after consonant
What are the 3 different disubstituted phenols?
Ortho (1,2)
Meta (1,3)
Para (1,4)
Physical properties of alcohols:
1) ______ bonding = higher b.p
2) polar bonds (_______ attractions)
3) hydrophilic (H2O): alcohols up to ____ carbons are miscible in water. In general each OH can carry ____ C into water
1) hydrogen
2) dipole
3) 3 C, 4 carbons needs tert-butyl
(IMPORTANT): A strong base can remove the hydroxy proton to give an _______
alkoxide (contains O-)
Alkoxide ions are strong _______ and strong _______
nucleophiles
bases
to form alkoxide ions, use ___ for (1° OH) or ___ for (2° or 3° OH) metal with ROH
Na
K
to form alkoxide ions that have phenol, ___ or ____ may be used to form the alkoxide
K or NaOH
- NaOH because of phenol pKa
to make C-C bonds using sp2 and sp3 carbons you need to make a _______ using Mg or Li
organometal
Organometals are strong ______ and strong _______
nucleophiles
bases
What are the two most common solvents used in a Grignard reaction
1) ether
2) THF
Keep in mind any ___ sources will react immediately with organometallic reagents!!!
H+
In a Grignard reaction, Mg undergoes _______ while Li undergoes _______
1) insertion
2) substitution
When organometallic reagents react with ketone, you need to use _______ acid to make 3° ROH to avoid E1 product
weak
What are the most common weak acids used for grignard reactions?
NH4Cl
H2O
When openening epoxide rings with Grignard reagents, basic conditions lead to nucleophile attack on the _______ hindered carbon
less
when making carboxylic acid formation via grignard reaction and CO2, the solvent used must be _______
H3O+
What is the gilman reagent?
R2CuLi
can gilman reagents be used in synthesis?
NO
When using gilman reagents, if the origninal molecule is cis db, the steroeochem is _______ and product is also cis
retained
What are the 2 most common hydride reagents?
1) NaBH4
2) LiAlH4
NaBH4 only reduces _______ and ______ while LiAlH4 reduces everything
aldehydes and ketones
LiAlH4 reactions must have ___ steps
2
1) LiAlH4, ether
2) H3O+
_______ allows catalytic hyrdogenation (reduction) of carbonyl groups and was made by an engineer in Chattanooga
Raney Ni
_______ are known as mercaptans, with the -SH group itself called a _______ group
Thiols
mercapto
sulfur molecules are named by adding the suffix _______ to the alkane name
thiol
thiols are _______ acidic than alcohols despite O being more EN because of _______
more
size
Thiols are made by _______ reaction so 1° alkyl halides work better
- will react twice and ends up R-S-R
SN2
- reacts twice cuz good Nucleophile
What reagent allows oxidation of thiol to disulfides?
Br2
What reagent allows reduction of disulfide to thiol
Zn, HCl
What reagent converts Thiols into sulfonic acids?
HNO3 (vigorous oxidation)
