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Ethers have boiling points similar to those of the analogous alkanes. Simple ethers are generally colorless.

This direct nucleophilic substitution reaction requires elevated temperatures (about 125 °C). The reaction is catalyzed by acids, usually sulfuric acid. The method is effective for generating symmetrical ethers, but not unsymmetrical ethers, since either OH can be protonated, which would give a mixture of products. Diethyl ether is produced from ethanol by this method. Cyclic ethers are readily generated by this approach. Elimination reactions compete with dehydration of the alcohol:

The dehydration route often requires conditions incompatible with delicate molecules. Several milder methods exist to produce ethers.

Williamson ether synthesis

Nucleophilic displacement of alkyl halides by alkoxides

In a related reaction, alkyl halides undergo nucleophilic displacement by phenoxides. The R–X cannot be used to react with the alcohol. However phenols can be used to replace the alcohol while maintaining the alkyl halide. Since phenols are acidic, they readily react with a strong base like sodium hydroxide to form phenoxide ions. The phenoxide ion will then substitute the –X group in the alkyl halide, forming an ether with an aryl group attached to it in a reaction with an SN2 mechanism.

The Ullmann condensation is similar to the Williamson method except that the substrate is an aryl halide. Such reactions generally require a catalyst, such as copper.

Electrophilic addition of alcohols to alkenes

Alcohols add to electrophilically activated alkenes.

Acid catalysis is required for this reaction. Often, mercury trifluoroacetate (Hg(OCOCF3)2) is used as a catalyst for the reaction generating an ether with Markovnikov regiochemistry. Using similar reactions, tetrahydropyranyl ethers are used as protective groups for alcohols.

Preparation of epoxides

Epoxides are typically prepared by oxidation of alkenes. The most important epoxide in terms of industrial scale is ethylene oxide, which is produced by oxidation of ethylene with oxygen. Other epoxides are produced by one of two routes:

• By the oxidation of alkenes with a peroxyacid such as m-CPBA.
• By the base intramolecular nucleophilic substitution of a halohydrin.

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• The bit patterns in the preamble and start of frame delimiter are written as bit strings, with the first bit transmitted on the left (not as octet values, which in Ethernet are transmitted least significant bit(s) first). This notation matches the one used in the IEEE 802.3 standard.
• Preamble and start frame delimiter are not displayed by packet sniffing software because these bits are stripped away at OSI layer 1 by the network interface controller (NIC) before being passed on to the OSI layer 2, which is where packet sniffers collect their data. There are layer-2 sniffers that can capture and display the preamble and start frame delimiter, but they are expensive and mainly used to detect problems related to physical connectivity.
• Minimum payload size is dictated by the 512-bit slot time used for collision detection in the Ethernet LAN architecture.
• A version 1 Ethernet frame was used for early Ethernet prototypes and featured 8-bit MAC addresses and was never commercially deployed.
• Original Ethernet frames define their length with the framing that surrounds it, rather than with an explicit length count.

Notes

• Cryptocurrency do not have a formal ISO 4217 alpha-3 code. “ETH” is informal only
• A permissionless network allows any party to participate in the network (e.g., conduct transactions) and contribute to its upkeep (e.g., consensus process) without any requirement to validate/approve its identity from a central authority.

The optional 802.1Q tag consumes additional space in the frame. Field sizes for this option are shown in brackets in the table above. IEEE 802.1ad (Q-in-Q) allows for multiple tags in each frame. This option is not illustrated here.

Ethernet packet – physical layer

The header features destination and source MAC addresses (each six octets in length), the EtherType field and, optionally, an IEEE 802.1Q tag or IEEE 802.1ad tag.

The EtherType field is two octets long and it can be used for two different purposes. Values of 1500 and below mean that it is used to indicate the size of the payload in octets, while values of 1536 and above indicate that it is used as an EtherType, to indicate which protocol is encapsulated in the payload of the frame. When used as EtherType, the length of the frame is determined by the location of the interpacket gap and valid frame check sequence (FCS).

The IEEE 802.1Q tag or IEEE 802.1ad tag, if present, is a four-octet field that indicates virtual LAN (VLAN) membership and IEEE 802.1p priority. The first two octets of the tag are called the Tag Protocol IDentifier (TPID) and double as the EtherType field indicating that the frame is either 802.1Q or 802.1ad tagged. 802.1Q uses a TPID of 0x8100. 802.1ad uses a TPID of 0x88a8.

Frame check sequence

The frame check sequence (FCS) is a four-octet cyclic redundancy check (CRC) that allows detection of corrupted data within the entire frame as received on the receiver side. According to the standard, the FCS value is computed as a function of the protected MAC frame fields: source and destination address, length/type field, MAC client data and padding (that is, all fields except the FCS).

However, hardware implementation of a logically right shifting CRC may use a left shifting Linear Feedback Shift Register as the basis for calculating the CRC, reversing the bits and resulting in a verify value of 0x38FB2284. Since the complementing of the CRC may be performed post calculation and during transmission, what remains in the hardware register is a non-complemented result, so the residue for a right shifting implementation would be the complement of 0x2144DF1C = 0xDEBB20E3, and for a left shifting implementation, the complement of 0x38FB2284 = 0xC704DD7B.

End of frame – physical layer

Interpacket gap (IPG) is idle time between packets. After a packet has been sent, transmitters are required to transmit a minimum of 96 bits (12 octets) of idle line state before transmitting the next packet.

Regulation

There are several types of Ethernet frames:

• Novell raw IEEE 802.3 non-standard variation frame
• IEEE 802.2 Logical Link Control (LLC) frame
• IEEE 802.2 Subnetwork Access Protocol (SNAP) frame

The different frame types have different formats and MTU values, but can coexist on the same physical medium. Differentiation between frame types is possible based on the table on the right.

In addition, all four Ethernet frame types may optionally contain an IEEE 802.1Q tag to identify what VLAN it belongs to and its priority (quality of service). This encapsulation is defined in the IEEE 802.3ac specification and increases the maximum frame by 4 octets.

The most common Ethernet Frame format, type II

Novell raw IEEE 802

Novell’s “raw” 802.3 frame format was based on early IEEE 802.3 work. Novell used this as a starting point to create the first implementation of its own IPX Network Protocol over Ethernet. They did not use any LLC header but started the IPX packet directly after the length field. This does not conform to the IEEE 802.3 standard, but since IPX always has FF as the first two octets (while in IEEE 802.2 LLC that pattern is theoretically possible but extremely unlikely), in practice this usually coexists on the wire with other Ethernet implementations, with the notable exception of some early forms of DECnet which got confused by this.

IEEE 802. 2 LLC

Some protocols, such as those designed for the OSI stack, operate directly on top of IEEE 802.2 LLC encapsulation, which provides both connection-oriented and connectionless network services.

IEEE 802.2 LLC encapsulation is not in widespread use on common networks currently, with the exception of large corporate NetWare installations that have not yet migrated to NetWare over IP. In the past, many corporate networks used IEEE 802.2 to support transparent translating bridges between Ethernet and Token Ring or FDDI networks.

IEEE 802. 2 SNAP

In IEEE 802.3x-1997, the IEEE Ethernet standard was changed to explicitly allow the use of the 16-bit field after the MAC addresses to be used as a length field or a type field.

The AppleTalk v2 protocol suite on Ethernet (“EtherTalk”) uses IEEE 802.2 LLC + SNAP encapsulation.

The C-O bonds that comprise simple ethers are strong. They are unreactive toward all but the strongest bases. Although generally of low chemical reactivity, they are more reactive than alkanes.

Although ethers resist hydrolysis, they are cleaved by hydrobromic acid and hydroiodic acid. Hydrogen chloride cleaves ethers only slowly. Methyl ethers typically afford methyl halides:

Ethers serve as Lewis bases. For instance, diethyl ether forms a complex with boron trifluoride, i.e. diethyl etherate (BF3·OEt2). Ethers also coordinate to the Mg center in Grignard reagents. Tetrahydrofuran is more basic than acyclic ethers. It forms complexes with many metal halides.

This reactivity is similar to the tendency of ethers with alpha hydrogen atoms to form peroxides. Reaction with chlorine produces alpha-chloroethers.

In the IUPAC Nomenclature system, ethers are named using the general formula “alkoxyalkane”, for example CH3–CH2–O–CH3 is methoxyethane. If the ether is part of a more-complex molecule, it is described as an alkoxy substituent, so –OCH3 would be considered a “methoxy-” group. The simpler alkyl radical is written in front, so CH3–O–CH2CH3 would be given as methoxy(CH3O)ethane(CH2CH3).

Polyethers are generally polymers containing ether linkages in their main chain. The term polyol generally refers to polyether polyols with one or more functional end-groups such as a hydroxyl group. The term “oxide” or other terms are used for high molar mass polymer when end-groups no longer affect polymer properties.

Crown ethers are cyclic polyethers. Some toxins produced by dinoflagellates such as brevetoxin and ciguatoxin are extremely large and are known as cyclic or ladder polyethers.

The phenyl ether polymers are a class of aromatic polyethers containing aromatic cycles in their main chain: polyphenyl ether (PPE) and poly(p-phenylene oxide) (PPO).

Many classes of compounds with C–O–C linkages are not considered ethers: Esters (R–C(=O)–O–R′), hemiacetals (R–CH(–OH)–O–R′), carboxylic acid anhydrides (RC(=O)–O–C(=O)R′).

History

After the Constantinople upgrade on 28 February 2019, there were two network upgrades made within a month late in the year: Istanbul on 8 December 2019 and Muir Glacier on 2 January 2020.

Design

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• Video which explains how to build an Ethernet Frame
• Minimum Frame Length in Ethernet explained

Applications

Oxygen is more electronegative than carbon, thus the alpha hydrogens of ethers are more acidic than those of simple hydrocarbons. They are far less acidic than alpha hydrogens of carbonyl groups (such as in ketones or aldehydes), however.

Ethers can be symmetrical of the type ROR or unsymmetrical of the type ROR’. Examples of the former are diethyl ether, dimethyl ether, dipropyl ether etc. Illustrative unsymmetrical ethers are anisole (methoxybenzene) and dimethoxyethane.

Vinyl- and acetylenic ethers

Vinyl- and acetylenic ethers are far less common than alkyl or aryl ethers. Vinylethers, often called enol ethers, are important intermediates in organic synthesis. Acetylenic ethers are especially rare. Di-tert-butoxyacetylene is the most common example of this rare class of compounds.

We may calculate the protocol overhead for Ethernet as a percentage (packet size including IPG)

We may calculate the protocol efficiency for Ethernet

Maximum efficiency is achieved with largest allowed payload size and is:

for untagged frames, since the packet size is maximum 1500 octet payload + 8 octet preamble + 14 octet header + 4 octet trailer + minimum interpacket gap corresponding to 12 octets = 1538 octets. The maximum efficiency is:

when 802.1Q VLAN tagging is used.

The throughput may be calculated from the efficiency

where the physical layer net bit rate (the wire bit rate) depends on the Ethernet physical layer standard, and may be 10 Mbit/s, 100 Mbit/s, 1 Gbit/s or 10 Gbit/s. Maximum throughput for 100BASE-TX Ethernet is consequently 97.53 Mbit/s without 802.1Q, and 97.28 Mbit/s with 802.1Q.

Channel utilization is a concept often confused with protocol efficiency. It considers only the use of the channel disregarding the nature of the data transmitted – either payload or overhead. At the physical layer, the link channel and equipment do not know the difference between data and control frames. We may calculate the channel utilization:

The total time considers the round trip time along the channel, the processing time in the hosts and the time transmitting data and acknowledgements. The time spent transmitting data includes data and acknowledgements.