Ch 10 Alcohols Flashcards Preview

Organic Chemistry I & II > Ch 10 Alcohols > Flashcards

Flashcards in Ch 10 Alcohols Deck (28)
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1
Q

synthesis gas

A

CO2 + 2 CO + 4 H2

2
Q
A

Nucleophilic Substitution on an Alkyl Halide

Usually via the SN2 mechanism; competes with elimination. Inversion of stereochemistry.

3
Q

Grignard reagent

A

The organomagnesium halides, of empirical formula R - Mg - X

4
Q
A

synthesis of a Grignard reagent

5
Q
A

synthesis of a Grignard reagent

6
Q
A

synthesis of a Grignard reagent

7
Q

what kind of solvent is required to synthasise a Grignard reagent?

A

a solvent containing the ether funtional group

8
Q

THF

A
9
Q

describe the formation of the Grignard reagent

A

Grignard and organolithium reagents provide some of the best methods for assembling a carbon skeleton. These strong nucleophiles add to ketones and aldehydes to give alkoxide ions, which are protonated to give alcohols.

Formation of the Grignard reagent: Magnesium reacts with an alkyl halide in an anhydrous ether solution.

10
Q

Explain the first step in carbon skeleton formation using a pre-made Grignard or organolithium reagent

A

Reaction 1: The Grignard reagent attacks a carbonyl compound to form an alkoxide salt.

11
Q

Explain the second step in carbon skeleton formation using a pre-made Grignard or organolithium reagent

A

Reaction 2: After the first reaction is complete, water or dilute acid is added to protonate the alkoxide and give the alcohol.

12
Q

How would you form a primary alcohol?

A

Addition of a Grignard reagent to formaldehyde

13
Q
A

Acid-catalysed hydration. Markovnikov orientation, syn addition.

14
Q

convert alkene to epoxide (diol), syn addition

A

Syn Dihydroxylation.

Osmium tetroxide (OsO4) and peroxides (H2O2)

-or-

Potassium permanganate (KMnO4) and hydroxide ion (-OH) (cold, dilute)

15
Q

Convert an alkene to an alcohol with Markovnikov orientation.

A

Acid-catalysed hydration.

16
Q

convert an alkene to an alcohol with Markovnikov orientation, anti addition.

A

Oxymercuration–demercuration. Hg(OAc)2 + H2O.

17
Q

convert an alkene to an alcohol, anti-Markovnikov orientation, syn addition.

A

Hydroboration–oxidation with peroxides.

(1) BH3 •THF, (2) H2O2, NaOH

18
Q

convert alkene to epoxide (diol), anti addition

A

Anti Dihydroxylation. peroxy acid (HCO3H) and hydronium (H3O+)

19
Q

convert grignard into a secondary alcohol with one additional carbon

A

Addition of a Grignard or organolithium reagent to an aldehyde.

(1) ether, (2) hydronium (H3O+)

20
Q

convert grignard into a primary alcohol with one additional carbon

A

Addition of a Grignard or organolithium reagent to formaldehyde.

(1) ether, (2) hydronium (H3O+)

21
Q

convert grignard into a tertiary alcohol with one additional carbon, with one of the final three R groups derived from the grignard reagent.

A

Addition of a Grignard or organolithium reagent to a ketone.

(1) ether, (2) hydronium (H3O+)

22
Q

convert grignard into a tertiary alcohol with one additional carbon, with two of the final three R groups derived from the grignard reagent.

A

Addition of a Grignard or organolithium reagent to an ester or acid halide (Cl shown).

(1) ether, (2) hydronium (H3O+)

23
Q

aldehyde to alcohol with no extra carbons added

A

NaBH4 (mild sauce)

or

LiAlH4 (hot sauce)

24
Q

ketone to alcohol with no extra carbons added

A

NaBH4 (mild sauce)

or

LiAlH4 (hot sauce)

25
Q

convert grignard into a primary alcohol with two additional carbons

A

Addition of a Grignard or organolithium reagent to ethylene oxide (an epoxide).

(1) ether, (2) hydronium (H3O+)

26
Q

carboxcylic acid anion in base to alcohol with no extra carbons added

A

LiAlH4 (hot sauce) ONLY

NaBH4 (mild sauce) NO RXN!

27
Q

ester to alcohol with no extra carbons added

A

LiAlH4 (hot sauce) ONLY

NaBH4 (mild sauce) NO RXN!

28
Q
A

Raney Nickel works like hot sauce (LiAlH4), but also hydrates and reduces carbon double bonds (C=C), making the product an alkane alcohol