Chapter 10 Flashcards

1
Q

The bond angle between H-O-H in water is _____

A

104.5

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2
Q

The bond angle between C-O-H in methyl alcohol is _____

A

108.9

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3
Q

When naming alcohols: drop the final e in the alkane name and replace with ___

A

ol

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4
Q

The longest carbon chain MUST be attached to the functional group _______, then # the chain so as to give that group priority

A

Winner (-OH)

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5
Q

The OH group is treated as a substituent named _______ when it appears on a structure with a higher priority functional group

A

hydroxy

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6
Q

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

A

diol or glycol
- needs e after consonant

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7
Q

What are the 3 different disubstituted phenols?

A

Ortho (1,2)
Meta (1,3)
Para (1,4)

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8
Q

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

A

1) hydrogen
2) dipole
3) 3 C, 4 carbons needs tert-butyl

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9
Q

(IMPORTANT): A strong base can remove the hydroxy proton to give an _______

A

alkoxide (contains O-)

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10
Q

Alkoxide ions are strong _______ and strong _______

A

nucleophiles
bases

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11
Q

to form alkoxide ions, use ___ for (1° OH) or ___ for (2° or 3° OH) metal with ROH

A

Na
K

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12
Q

to form alkoxide ions that have phenol, ___ or ____ may be used to form the alkoxide

A

K or NaOH
- NaOH because of phenol pKa

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13
Q

to make C-C bonds using sp2 and sp3 carbons you need to make a _______ using Mg or Li

A

organometal

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14
Q

Organometals are strong ______ and strong _______

A

nucleophiles
bases

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15
Q

What are the two most common solvents used in a Grignard reaction

A

1) ether
2) THF

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16
Q

Keep in mind any ___ sources will react immediately with organometallic reagents!!!

A

H+

17
Q

In a Grignard reaction, Mg undergoes _______ while Li undergoes _______

A

1) insertion
2) substitution

18
Q

When organometallic reagents react with ketone, you need to use _______ acid to make 3° ROH to avoid E1 product

A

weak

19
Q

What are the most common weak acids used for grignard reactions?

A

NH4Cl
H2O

20
Q

When openening epoxide rings with Grignard reagents, basic conditions lead to nucleophile attack on the _______ hindered carbon

A

less

21
Q

when making carboxylic acid formation via grignard reaction and CO2, the solvent used must be _______

A

H3O+

22
Q

What is the gilman reagent?

A

R2CuLi

23
Q

can gilman reagents be used in synthesis?

A

NO

24
Q

When using gilman reagents, if the origninal molecule is cis db, the steroeochem is _______ and product is also cis

A

retained

25
Q

What are the 2 most common hydride reagents?

A

1) NaBH4
2) LiAlH4

26
Q

NaBH4 only reduces _______ and ______ while LiAlH4 reduces everything

A

aldehydes and ketones

27
Q

LiAlH4 reactions must have ___ steps

A

2
1) LiAlH4, ether
2) H3O+

28
Q

_______ allows catalytic hyrdogenation (reduction) of carbonyl groups and was made by an engineer in Chattanooga

A

Raney Ni

29
Q

_______ are known as mercaptans, with the -SH group itself called a _______ group

A

Thiols
mercapto

30
Q

sulfur molecules are named by adding the suffix _______ to the alkane name

A

thiol

31
Q

thiols are _______ acidic than alcohols despite O being more EN because of _______

A

more
size

32
Q

Thiols are made by _______ reaction so 1° alkyl halides work better
- will react twice and ends up R-S-R

A

SN2
- reacts twice cuz good Nucleophile

33
Q

What reagent allows oxidation of thiol to disulfides?

A

Br2

34
Q

What reagent allows reduction of disulfide to thiol

A

Zn, HCl

35
Q

What reagent converts Thiols into sulfonic acids?

A

HNO3 (vigorous oxidation)